Big news for Caribbean cruisers: Nanny Cay Marina on Tortola has begun construction on a major expansion that will add a third marina basin, increase haulout capacity and create new berthing for the growing fleet of large catamarans and luxury yachts cruising the Caribbean.

The development includes a custom Marine Travelift designed for 60- to 80-foot multihulls, 112 new slips for catamarans, private boats and yachts up to 165 feet, and expanded yard space. The investment is expected to exceed $30 million and will roll out over three years.

“This expansion reflects our ongoing commitment to improving facilities for the BVI’s marine community and strengthening Nanny Cay’s position as the heart of Caribbean yachting,” said Cameron McColl, chairman of Nanny Cay. He noted that increased lift capacity and berthing will help serve “the growing number of large catamarans and superyachts operating in the region.”

General Manager Miles Sutherland-Pilch said the demand has been clear. “We were seeing increasing demand from larger multihulls and monohulls, and this project was designed to meet that need,” he said. “The new lift and berths will allow us to handle more vessels efficiently and safely.”

BVI Premier Dr. Natalio Wheatley called the expansion the first phase of a broader redevelopment plan for the resort and marina. He said the project represents “a declaration of confidence in our economy, our people and in the Virgin Islands as a premier destination for tourism, maritime excellence and sustainable growth.” Wheatley also highlighted the plan’s workforce impact, citing 91 new jobs and a training partnership with H. Lavity Stoutt Community College.

Along with expanded marine services, the project includes customer amenities like a new beach, pool, restaurants, retail village and a dedicated classroom for youth maritime programs. Nanny Cay will also continue to serve as home base for the BVI Spring Regatta and Sailing Festival, which will celebrate its 53rd running in 2026.

With the BVI continuing to attract passagemakers, charter guests and long-range cruisers, the expansion aims to keep pace with the next generation of cruising platforms while reinforcing the territory’s reputation as one of the Caribbean’s premier boating destinations.

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Lagoon, the world leader in cruising catamarans, is expanding its partnership with Ponant Yachting and Sailoé with a new flagship model, the Lagoon EIGHTY 2. The catamaran, named Spirit of Ponant II, will begin operating luxury charters in French Polynesia by late 2026.

The announcement marks the third yacht in Ponant Yachting’s growing fleet, joining Spirit of Ponant in the Seychelles and La Désirade, which splits its season between Corsica and the Caribbean. Each catamaran in the program is designed for small-group exploration, offering a more personal and environmentally conscious sailing experience.

Built at Lagoon’s Bordeaux facility, the EIGHTY 2 reflects the builder’s focus on elegance, performance, and sustainability. With more than 400 square meters of living space, five double cabins, and a four-person crew, the new yacht is designed for fully private charters and tailored itineraries. Guests can expect a mix of refined comfort and hands-on water adventure, including an array of high-end water sports.

“The Spirit of Ponant II reflects the natural evolution of a partnership based on shared values: excellence, innovation, and respect for the environment,” said Thomas Gailly, Lagoon’s Brand Director. “We are honored to support Ponant Explorations Group in developing its premium sailing offering, with a yacht that raises the bar for luxury at sea.”

The project underscores an ongoing alliance between three French yachting leaders. Ponant Explorations Group, renowned for small-ship luxury expeditions, Sailoé Yachting, specialists in Lagoon charters worldwide, and Lagoon, a brand of the Beneteau Group, continue to shape what they describe as “a more intimate and inspiring” style of ocean travel.

With a growing fleet spanning multiple oceans, Ponant Yachting says it aims to redefine modern luxury under sail, matching slow travel, sustainability and seclusion with world-class comfort.

The post Lagoon and Ponant Expand Luxury Sailing Fleet appeared first on Cruising World.

There’s nothing quite like the first sip of rum at anchor, the light dimming on the sea, the scent of salt and sugarcane in the air. For me, the daily craving started with a gallon jug of punch on a bareboat charter back in 1979. Since then, Caribbean rum and I have had a long, spirited relationship—one sip at a time, one island at a time.

The seventh-annual Caribbean Rum Awards were held this past fall on St. Barts. This competition is all about ­sipping rums, not the more-pedestrian versions used for mixing evening cocktails, where most any good rum will do. Out of 60 rums entered, Martinique’s Trois Rivières Triple Millésime was crowned world ­champion. Kudos to the French.

One of the great joys of sailing the Eastern Caribbean is sampling various island rums as you go. I’ve been doing this for 46 years, ever since a two-week bareboat charter in the Virgin Islands. The boat, a Morgan Out Island, was wide-beamed, lumbering, and about as elegant as a camper van in a cocktail dress. But tucked beside the chart table sat a complimentary gallon jug of rum punch, sweating in the tropical heat.  

That did it. It’s been rum ever since.

Rum is the Caribbean in a glass: sun-warmed sugarcane, salt-laced breezes, and the echo of steel drums somewhere ­onshore. Made from local sugarcane or molasses, rum reflects its birthplace in flavor and color, from crystal clear to ­molasses black. West Indian rum is available in clear or in shades from gold to amber to black. Mix the amber fluid with pineapple and orange juice, add a splash of grenadine, and the drink takes on all the colors of a West Indian sunset.

In the early days, it was always Mount Gay and orange juice for me: simple, cheap, and potent enough to cut through the heat after a long sail. That was in the 1980s, when I could buy a bottle on St. Barts, duty-­free, for $2. And while my rum locker still contains a few bottles of select sipping rums, in more recent times, Cruzan Aged Dark has supplied my daily ration. This reasonably priced amber rum is distilled on St. Croix in the US Virgin Islands. 

I start with a 24-ounce insulated Yeti coffee mug—it keeps the morning coffee hot and the evening rum chilled, both for hours. Drop in four cubes of ice and 4 ounces of rum, and top it off with 18 ounces of tonic water. A squeeze of lime is ­optional, and dash of nutmeg is nice. 

Each island down here has a distillery or two. Some of these island rums are excellent, most are good, and a few should come with a fire-hazard warning. I once tried a bottle from a roadside shack in Dominica that could’ve doubled as outboard fuel. 

On Grenada, Clarke’s Court and River Antoine produce their own rums. On Bequia, I found Sparrow’s, a rum from St. Vincent. It was just right for mixing my evening libation. On Bermuda, Goslings makes a dark rum that, when combined with ginger beer, becomes a Dark ’n Stormy. Guadeloupe and Martinique have their own distilleries, producing robust French-style rums. On Sint Maarten, Guavaberry and Topper’s offer a dozen spiced and gussied-up varieties. Callwood Rum Distillery in Cane Garden Bay on Tortola has been making rum for more than 200 years. The stone buildings, scorched copper stills and weathered casks feel frozen in time. Callwood’s signature 80-proof cane-based rum—named Panty Dropper—is as famous for its label as its lingering kick.

Rum is the ­Caribbean in a glass: sun-warmed sugarcane, salt-laced breezes, and the echo of steel drums somewhere onshore.

Antigua Distillery Limited offers a variety of sipping rums. Its Cavalier Gold is a fine choice for any West Indian rum punch. If you’re lucky—or persistent—you might find yourself invited to join the Royal Navy Tot Club of Antigua and Barbuda. Under the glow of nautical lanterns in a dockside pub, a band of expats gathers nightly to toast the Crown and history itself. A Royal Navy tale is read aloud, and a full tot of rum—2.4 ounces, not a drop less—is downed in one steady gulp. Saturdays come with the toast: “To our wives and ­sweethearts, may they never meet.”

In 1999, I made my way to Cuba and found myself a few blocks behind El Capitolio in Central Havana, at a place called El Floridita, which Ernest Hemingway once haunted like a regular spirit. This pink, one-story restaurant and bar is eight blocks in a straight line down Obispo Street from the Hotel Ambos Mundos, where Hemingway lived for a while. He would drink a dozen daiquiris in one sitting while chatting with fellow writers such as Ezra Pound, John Dos Passos, Graham Greene, Jean-Paul Sartre, Gabriel García Márquez and Tennessee Williams. The photographs on the walls tell a more complete story from the 1930s to 1950s.

My red-aproned bartender—sleeves rolled, a practiced flick of the shaker—lined up daiquiris like a gunslinger. Rum, lime, grapefruit juice, sugar syrup. Shake. Pour. Repeat. According to William Grimes’ book Straight Up or On the Rocks: The Story of the American Cocktail, this traditional drink is made with Bacardi white rum, fresh lime, grapefruit juice and sugar syrup. It’s shaken, not stirred, with ice, and is served in large goblets. Add six drops of maraschino liqueur for more color. If the bartender skips the sugar, it’s the Hemingway Daiquiri: stripped down, no-nonsense and a little dangerous. Where the classic version is limey and sweet, this one doubles the rum, earning the nickname “Papa doble.” It’s a drink that doesn’t smile back, and after two, neither will you.

Bacardi rum is not available in Cuba now, yet the name is still in Havana, carved into a granite facade—the family’s former headquarters. Today, the rum in Cuba is Havana Club. The Bacardi family set up shop in nearby Puerto Rico and is doing just fine.

Puerto Rico’s piña colada is a sweet, slushy anthem to ­vacation-­mode excess. It’s served in ­hurricane glasses taller than your forearm, usually with a cherry and a paper umbrella. It tastes like sunblock and joy. I once ordered one that came in a hollowed-out pineapple—and briefly considered renting a ­cabana and staying forever. 

For sailors, there’s Navy Grog, made with Pusser’s Rum, water and lime juice. This daily tot was first doled out to British crews in 1655 and then stopped in 1970. The Royal New Zealand Navy still continues the tradition. 

The Painkiller is the BVI’s answer to the mainland’s ibuprofen and acetaminophen—a creamy, coconut-laced concoction that masks its potency behind pineapple sweetness and a dusting of nutmeg. I had my first Painkiller at the Soggy Dollar Bar, slumped in a hammock after a beach landing that required no shoes and one waterproof dry bag. The drink originated at White Bay on Jost Van Dyke, where there’s no dock. Sailors swim ashore with dollar bills stuffed in their swimsuits. The Painkiller goes down really easy. By the second round, the name starts to make perfect sense. It comes in grades: one, two, three—and the fourth should be outlawed. 

On the other hand, rum punch is the Caribbean’s catchall cure: orange juice, pineapple juice, grenadine, a dash of lime and whatever rum’s on hand, often two or three kinds. I’ve had versions so smooth that they sipped like juice, and others that lit up my sinuses like wasabi. The only ­constant? You don’t stop at one. The recipe starts with ice in a tall glass, ­followed by white or amber rum, then tropical citrus fruit juices such as lime, lemon, papaya, mango, pomegranate and orange. I prefer pineapple and ­orange juice with a splash of grenadine syrup for color.

On Bequia, a variation of rum punch goes like this: one of sour, two of sweet, three of strong and four of weak. That’s lime juice, sugar syrup, rum and tonic water.

The mojito is Cuba’s contribution to the rum drinker’s delight. In my opinion, having done the Hemingway Pub Crawl, Hotel Ambos Mundos makes the best one. Hemingway wrote 1932’s Death in the Afternoon here, about Spanish bullfights. He also started writing Green Hills of Africa here, and worked on To Have and Have Not. The mojitos at this bar come with a sprig of mint so fresh, it still holds the scent of the garden. That mint goes into a tall glass with a lime wedge and a spoonful of sugar, to be mashed into a fragrant pulp by a mallet worn smooth from good use. Then it’s ice, Havana Club rum, soda water, a straw, and a nod from the bartender. The mojito is a refreshing drink with the fiery taste of rum tamed by sugar, lime and grass. One usually leads to two. 
Of course, not every rum drink comes in a frosted glass. Sometimes it’s a tin mug of grog—rum, water, lime and not much else—passed around at anchor as the sun drops. No umbrellas, no fanfare. Just sailors, stories, and a slow burn in the chest.

As I sail among the islands this winter, I’ll be hunting cocktails as much as coves. It’s a ritual now. As the hook sets and the light fades, I head below, reach for the rum, and pour my daily ration. The sea sighs against the hull, and the scent of lime is on my hands as I raise a glass to the islands, to Hemingway, and to another day well-lived under sail. 

For more than 20 years, author and ­photojournalist David H. Lyman has sailed the Eastern Caribbean islands. His Hemingway Pub Crawl is detailed in his forthcoming book, A Maine Yankee in Castro’s Cuba. Find more of his writing and photographs at dhlyman.com. 

The post Caribbean Rum: A Sailor’s Spirited Journey appeared first on Cruising World.

Chartering is guaranteed to teach you something. Sometimes it’s a gentle lesson, such as discovering the pure joy of a quiet anchorage that wasn’t even on your itinerary. Sometimes it’s more like a slap from a wet halyard. Either way, every charter adds a few notches to your sailing know-how—and your humility.

Over the years, I’ve come to think of charter trips less as vacations and more as continuing education. Each time out, there’s a new wrinkle: a mystery beep from the nav station, a stubborn mooring ball, a provisioning mishap that results in 5 pounds of cheese slices and no coffee. And so I’ve started keeping an informal mental list—call it the “charter charter.” These aren’t hard rules, exactly, and they’re certainly not gospel, but they are things I’ve learned, usually by doing them the hard way.

Like provisioning. Charter boats are ­often floating paradises, but they are not bottomless pantries. Let your crew loose in a shoreside market without supervision, and you might end up with nothing but snacks, mixers and a healthy debate about whether Coffee mate counts as a dairy substitute. My advice? Appoint a provisioning captain, make a list and, above all, do not forget the coffee. Pro tip: Paper towels can double as coffee filters. You’re welcome. 

Packing falls into a similar category. Every charter begins with someone dragging an oversize rolling duffel onto the dock like they’re about to fly to the French Riviera. Don’t be that person. You’ll end up wearing the same pair of shorts, the same salt-crusted T-shirt and the one hat that doesn’t fly off in 20 knots of trade wind. The rest of it? Deadweight. But if you’re a coffee connoisseur, do pack your favorite beans. Just trust me.

Your crew—whether familial or familiar​—have their own internal ecosystem too. There’s always someone who insists on organizing the itinerary down to the minute, complete with tide tables, wind models and backup anchorages in three languages. Let them. Every crew needs a logistics geek. But every crew also needs a “just happy to be here” type, and someone who insists on helping out with the daily onboard chores. Like dishes. This person is a saint. Extra grog rations might be in order.

As for sailing itself, the gear might get fancier every year, but the sea doesn’t care how many USB outlets your boat has. Batteries still run down, anchorages still get rolly, watermakers may or may not decide to stop making water halfway through the voyage, and marine toilets still operate on black-magic principles. Explaining “pump, pause, pump” to a landlubbing friend is a rite of passage. So is the awkward moment when someone insists that they never get seasick—right before turning the color of Key lime pie.

Then there’s the matter of anchoring. Modern catamarans are wide, comfortable and basically floating condos—but they still swing on a single hook, and scope is not a vibe. Learn the anchoring system. Communicate. Don’t be the crew who drifts too close to the boat flying the dive flag. 

Charter boats these days come tricked out with more amenities than ever. I’ve chartered some that were better equipped than my last apartment. But that doesn’t mean the experience has lost its charm. In fact, the beauty of chartering is in the freedom. You’re not locked into a set itinerary. You don’t have to tick off every must-see beach bar. Some of the best moments come when you go off-script—when weather changes your plan, or when you decide to linger an extra day in that perfect little bay because the breeze feels just right.

And those moments stick with you. That’s what chartering does. It gives you stories. Like the time we set out for what we thought would be a mellow downwind sail and ended up motoring through a dead calm, dodging squalls and learning how to make cocktails with exactly three ­remaining ice cubes. 

The memories that matter aren’t always the picture-perfect ones. They’re the ones where you figured out something together, adjusted on the fly, and laughed about it at the dinner table. Smooth sailing is nice, but a little friction makes the lobster tails taste better and the stories funnier.

Whether you’re eyeing the Med, the Caribbean or the Pacific Northwest—or you’re not quite sure where to begin—if this is your year to finally book that long-awaited charter, get it done. Book the boat. Gather your crew. Toss your flip-flops into a duffel bag and go. The boat might be borrowed, but the dream is all yours.

May you see fair winds, light packing lists, and just the right amount of ice for your Painkillers.

The post The Charter Charter: Lessons from Sailing Adventures appeared first on Cruising World.

For many sailors, the dream of owning a yacht in the Virgin Islands is as picture-perfect as the Caribbean itself. But for some, that dream is also a strategic move that blends lifestyle, business and, in some cases, tax-smart investing. Crewed charter-yacht ownership can be a viable path to spending real time on the water while defraying the costs of boat ownership.

Cruising World Editor-in-Chief Andrew Parkinson sat down with charter expert and BVI Yacht Sales broker Ted Reshetiloff for a deep dive into the world of charter-yacht ownership, based on his personal interactions with client-owners, brokers and charter operators. 

AP: Let’s start with the basics. Why would someone choose to own a professionally crewed charter yacht instead of using the boat solely for private enjoyment?

TR: It’s a great question, and one we hear often from potential buyers weighing their ­options. The truth is, there are a number of compelling reasons why someone might choose the crewed charter model over traditional private ownership—starting with lifestyle and access.

For many people, the idea of owning a 50-plus-foot catamaran is incredibly appealing, but the financial and logistical realities can be a deal-breaker. Purchase price, insurance, dockage and annual upkeep add up quickly. Then there’s the challenge of managing the boat—often located in the Caribbean or Mediterranean—while living thousands of miles away. It’s a full-time commitment that doesn’t align with most owners’ lifestyles.

That’s where the crewed-yacht model offers real advantages. By placing the vessel into a professional charter program with full-time crew, many of those burdens are lifted. Owners can enjoy peace of mind knowing that the boat is being actively maintained and operated by professionals. In fact, we often see better long-term care in crewed yachts than in those that sit idle between seasonal owner visits.

Financially, there’s an upside as well. Most crewed yachts for sale come with existing ­bookings in place, providing immediate revenue and an established client base. While it’s not a get-rich scheme, the ­charter income can offset a ­significant portion of the ownership costs​—and in some cases, even ­generate passive or semi-active income.

But beyond the dollars and logistics, what really motivates many owners is the lifestyle enhancement. Charter ownership offers flexibility, access to a premium yacht, and the ability to share unforgettable experiences with friends and family, all while knowing that your asset is working for you when you’re not aboard. For many, it’s the gateway to a yachting life that they otherwise couldn’t justify or afford.

AP: What do the numbers really look like? How do owners balance personal use with ­generating charter income?

TR: Once you own a crewed yacht in the Caribbean, the dream starts to take shape. You’re planning your next getaway and imagining anchoring off secluded beaches, with a ­cocktail in hand. But then comes the real question: How many weeks a year do you actually plan to spend on board? And is this primarily a lifestyle play or a financial one?

Owners need to decide early on how much charter activity they want. Some aim to maximize income, booking 20 or more weeks per season to make the most of high-demand charter windows. Others take a more balanced approach, modeling out their expenses and choosing to charter just enough to offset annual costs while preserving prime weeks for personal use.

Charter rates vary based on the boat, but to give you an idea, a crewed Leopard 50 catamaran can bring in around $25,000 per week for an ­all-inclusive charter. So, if you’re asking yourself, Is it cheaper to own or to charter? then you need to compare apples to apples. Let’s say you want to spend eight weeks a year sailing the islands. Chartering a comparable crewed yacht for that amount of time could easily cost you upwards of $200,000 annually. But as an owner, those weeks can be paid for by your charter income—and you’re spending them on a professionally crewed, well-maintained yacht that’s yours.

So the financial equation ­really comes down to how much you use the boat and how you value the lifestyle. For many owners, it’s not just about the numbers. It’s about accessing a level of experience that they couldn’t otherwise justify or afford without the charter model in place.

AP: Are there any tax benefits to owning a crewed charter yacht?

TR: Absolutely—and it’s one of the most important parts of the conversation for US-based ­buyers. Under the right circumstances, there are several tax strategies that can significantly reduce the cost of ownership, particularly if the yacht is operated as a legitimate business with the intent to generate profit. That said, these benefits are complex and must be carefully structured in consultation with a tax professional who understands maritime assets.

One of the key areas where owners might find advantages is bonus depreciation. This has been one of the most powerful incentives in recent years. If a yacht qualifies as a business asset, owners might be able to depreciate a significant portion of the purchase in the first year. Under the Tax Cuts and Jobs Act, that meant up to 100 percent depreciation, though this percentage has started to phase down. Still, there are signals that it might return to the full deduction under new legislation. To qualify, you must be operating the yacht as a ­bona fide business.

Another advantage can be the Section 179 deduction. Similar to bonus depreciation, Section 179 allows for the immediate expensing of certain business assets, including—​under the right conditions—charter yachts. It’s subject to limits, but it can be a valuable tool for those looking to reduce taxable income early in ownership.

There’s also deductible operating expenses. If the yacht is actively chartered and treated as a business, many ongoing costs might be deductible. That includes dockage, maintenance, crew salaries, insurance, fuel, provisioning, marketing, and even travel expenses ­related to managing the yacht.

Loan-interest deduction is another possible advantage. If you finance the purchase, the interest on that loan also might be deductible—again, provided the yacht is used for legitimate business purposes. This can ease the financial load, especially in the early years of ownership.

With sales tax, depending on how the purchase is structured and where the vessel is delivered, some owners can defer or even avoid paying sales tax altogether. Some take delivery in tax-advantaged jurisdictions or form ownership entities in states or territories with more-favorable laws.

Also worth noting is that the IRS draws a line between active and passive income. If you’re materially involved in running the charter business, you might be able to offset losses against other active income. If it’s considered a passive activity, the benefits are still there but ­applied differently.

There’s also the 1031 like-kind exchange. This applies mostly to real estate, but there have been instances where commercial yacht owners have successfully used this strategy to defer taxes when upgrading to a newer vessel. It’s not common, but it’s worth exploring with your CPA if you’re scaling up.

Bottom line: The tax advantages can be substantial, but they require intentional planning, proper documentation and professional guidance. For many owners, the savings can help make the numbers work and turn a luxury purchase into a viable investment.

AP: What’s the deal with buying a crewed charter yacht that’s already up and running, with bookings already lined up?

TR: For buyers looking to step into the charter world with minimal friction and maximum financial upside, purchasing a turnkey crewed yacht with existing bookings is a smart move. These yachts are already up and running, often with a full calendar of charters secured months in advance. That means you’re not starting from scratch. You’re stepping into a revenue-generating business from day one.

One key benefit of that approach is immediate cash flow. Yachts with active charter schedules typically come with prebooked weeks—sometimes a full season or more. That gives new owners immediate income, which can help offset expenses right out of the gate.

There’s also the established market presence. A boat that’s been operating successfully has something money can’t easily buy: reputation. Repeat clients, positive reviews and name recognition all can lead to consistent bookings year after year.

Also, most turnkey yachts are sold with a seasoned crew already on board and a trusted management company running day-to-day operations. That means you’re buying into a system that works: Everything from maintenance and provisioning to client service is ­handled by professionals.

If you want hands-off ownership, this is a way to get it. Not every owner wants to be involved in the logistics of running a charter business, and with a well-managed operation, you don’t have to be. Many owners simply enjoy their owner-­use weeks and let the team handle the rest.

In the Virgin Islands especially, many of these operations are supported by experienced clearinghouses, which are local charter hubs that manage bookings, hold client deposits, oversee crew contracts and help navigate local regulations, ­including work permits and customs compliance.

For buyers who want a blend of lifestyle and financial return, a turnkey charter yacht offers one of the most efficient paths to ownership. It’s a proven model with fewer unknowns—and a faster route to making your dream yacht work for you.

AP: How do owners structure their yacht purchases?

TR: There’s no one-size-fits-all model, but many owners have built successful operations by combining smart tax planning, realistic income goals, and a clear understanding of what they want from ownership, whether it’s lifestyle, income or both.

Some owners set up legitimate yacht-charter businesses, allowing them to take advantage of tax incentives such as depreciation and deducting operating expenses. Others get creative with financing and ­entity structures to optimize their tax position and cash flow. The common thread is that they’re working with experienced professionals—brokers, tax advisers, maritime attorneys—who understand how to structure things properly.

From the clearinghouse perspective, I agree with Dick Schoonover at CharterPort BVI. He says that for most crewed catamarans, the typical break-even point for a 40- to 50-footer is around 10 to 12 charters a year. At that size, annual crew costs for a captain and chef can run around $1,800 per foot. Many crews aim to book 20 or more weeks per year, motivated not just by salary but also by guest gratuities.

With the larger luxury cats, such as Lagoon 620s and 70- to 80-foot Sunreefs, the owner will need more-experienced crews and bigger budgets. Those boats can charter for $100,000 or more per week. Owners might see only 10 to 15 charters a season, but at that rate, the math can still make sense.

Schoonover does caution that after about five years in charter service, a yacht typically needs a refit. At that point, owners either invest in the upgrade or list the boat for sale—often with a strong charter track record and client base that adds real market value.

And one other note: A small number of top charter brokers control the majority of bookings. So aligning with the right team—on the dock and in the marketplace—is key to ­long-term success.

For anyone considering this path, hearing these real-world stories can make the possibilities feel a lot more tangible. With the right setup, it can be both a smart investment and a deeply rewarding lifestyle.

AP: Any parting advice for someone thinking about taking the plunge into crewed ­charter-yacht ownership?

TR: At the end of the day, owning a crewed charter yacht—­especially one based in the Virgin Islands—is about finding the right balance between lifestyle and financial sense. Some folks are drawn to the tax benefits, others to the idea of stepping into a business that helps offset the cost of owning a beautiful yacht in paradise. And for many, it’s a bit of both.

But here’s the real ­takeaway: This isn’t the kind of thing you want to figure out alone. Between the charter ­regulations, tax angles, crew ­logistics and quirks of Caribbean ownership, there are a lot of moving parts. It just makes sense to talk to people who’ve helped others do it ­before—ideally folks who live and breathe this world year-round.

Whether you’re looking at a ready-to-go yacht with bookings already on the calendar or dreaming about refitting a boat into your ideal floating getaway, getting the right info up front can save you time, money and headaches down the road. 

Owning a crewed yacht can be incredibly rewarding. It just helps to go into it with your eyes wide open and a good chart to follow. 

The post The Charter Equation: How To Unlock Yacht Ownership Benefits appeared first on Cruising World.

For the fifth year in a row, The Moorings has been recognized with Tripadvisor’s Travelers’ Choice Award in the “Things To Do” category for its charter operations in the British Virgin Islands. The award places The Moorings among the top 10 percent of attractions worldwide based on consistently strong guest reviews.

“Winners are calculated based on the quality and quantity of the millions of reviews, opinions, and ratings collected on Tripadvisor,” the company explains. “With over 8.7 million businesses listed on Tripadvisor, these awards are a true testament to the outstanding service and quality that winners consistently provide to their guests.”

The recognition comes as The Moorings’ BVI base has undergone significant transformation in recent years. Following the devastation of Hurricane Irma in 2017, the company invested in a comprehensive rebuild of its flagship location. Improvements include new docks, a renovated hotel, an on-site supermarket, and a refreshed fleet featuring the latest cruising catamarans and monohulls.

“We are thrilled to have been awarded this award once again,” says Ian Pedersen, Senior Marketing Manager for The Moorings. “It is a testament to the hard work that has gone into rebuilding our flagship destination in the past few years, and a validation that the changes we have implemented are having the desired positive impact for our guests.”

With more than five decades of charter expertise, The Moorings remains one of the most recognized names in global yacht chartering. For many sailors, the British Virgin Islands continue to represent a quintessential cruising ground, with steady trade winds, protected anchorages, and short passages between islands—an ideal setting for a first-time or repeat charter vacation.

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I called my brother Dan, who is my go-to guy for half-baked, far-flung sailing ideas. “The time is now,” I said, using an ominous voice. “Time for us to head north for some serious sailing adventure.”

No, I was not talking about the San Juan Islands, that delightful archipelago in the far northwest corner of the contiguous United States. I wanted to cross the border, where the magic continues with Canada’s Gulf Islands.

Like a baby whale tucked safely up against its mother’s belly, the 200 or so Gulf Islands are clustered around the southeast corner of Vancouver Island at the western terminus of the world’s longest international border. They benefit from the rain-shadow effect of the mountains there, with a mild, sunny climate and limited rain and snow. It’s a perfect place for two guys who spend their ­summers wilting in the heat of Florida and California.

I reminded myself, as I searched for a charter company, to ask questions and do actual research about boat maintenance and more before sending the check. This credo led me to the good people at NW Explorations, who had excellent customer reviews and a gently used Bavaria 35 available for our preferred dates in September. The ­company also scores big on ­convenience: It’s all of 10 minutes from Victoria International Airport.

One thing I kept reading on ­social media is that recreational boats need to be wary of the many ferries and floatplanes that use these ­waters. With shock, I watched a 2023 ­video of a floatplane colliding with a ­powerboat in Vancouver Harbour. And ferries are always going faster than they look. So I paid close attention on arrival day at Port Sidney Marina as I learned all about the Bavaria Immaterial Girl. 

A company rep helped us review safety gear, electronics and engine operation. She produced maintenance checklists. This was comforting compared with previous charters I’ve been on, where the company neglected to empty the holding tank or make sure all the battery cables were tight. 

Another rep then demonstrated the finer points of operation, navigating and anchoring. “The few problems we’ve had,” he said, “were customers who hit a rock and said it was unmarked. There are no unmarked rocks in this area. They’re all on the chart.”

Dan arrived from the airport a little before dusk. After loading up on food and drinks, we reviewed tides and weather, and we set the alarm for dawn. We would try to catch a break with the wind early in the week, get as far north as possible, and then pick our way south through the islands. For wind and weather forecasts, we had the internet and real-time updates. 

We motored out of the marina the next morning and were ­treated to a sublime display of rocky islands and mountains backlit by a golden sky. The florid writing of Muriel “Capi” Blanchet came to mind. She sailed these waters on a small motor launch with her five children almost 100 years ago, using the experience as ­inspiration for her Canadian classic, The Curve of Time.

I’ve spent a lot of time on boats, mostly on the US East Coast and in the Bahamas. I can tell you now that the only thing that those locations have in common with these waters is salt, storms and tides. In our warm waters, you’ll see birds and the occasional ­manatee, but up here, you’re constantly goose-necking to see pelagic life, to take it all in. I’m embarrassed to say that in all my sailing, I’d never seen a whale and was quietly hoping that a pod would make an appearance. And the soundings can go from 300 feet to less than 10 in a New York minute. 

The wind was foul but the mood was fine as we picked our way through the many isles and tidal streams. For navigation, we had paper charts and a chart plotter. The Navionics app on my phone proved the most useful; it instantly plotted our way through minefields of rocks and narrow passes. Still, I frequently cross-checked our position on all three redundant systems.

Archipelago sailing is great. You sail as long as you like and then pull over wherever you are for the night. Weary of the strong northwesterlies, we gingerly entered Princess Cove on Wallace Island, dropped a single anchor, and called it a day. At sunset, we were treated to a full harvest moon rising above the pines with a million stars above. 

The next morning, we listened to Environment Canada’s marine forecast on VHF radio Channel 21 and got underway beneath a beautiful sky on a falling tide, backtracking oh-so-slowly, with a sharp eye on the depth sounder as we reentered Trincomali Channel, bound for Gabriola Island. We raised the mainsail with the wind still forward of the beam.

Seas were smooth, and we maintained 5 knots with motor assist. Later, we passed a tug with a log boom—a reminder that we shared these waters with slow-moving working vessels. John Muir passed near here in 1879 on his way to Alaska and was astonished by what he saw. “Never before this had I been ­embosomed in scenery so hopelessly ­beyond ­description,” he wrote.

Good time is made catching the rising tide, and by afternoon, we had pulled into Degnen Bay on Gabriola, where we were disheartened to see boats chockablock on moorings. Dan took the helm while I scanned around. Canadian kindness is real: With a big smile and without being asked, a man offered his mooring to us for the night, then ran his dinghy out to show us where and took our bow line through the swivel eye. He refused to take any money. Then he got his car and offered us a ride to town. Wow, what a great place.

In Folklife Village, we picked up a few items for the larder and then caught “Gertie,” the public bus service. It makes continuous loops around the island and requires only a wave to the driver for a ride. And on this island, like all the others we visited, there were constant reminders that First Nations people had been there long before the Europeans arrived.

On day three, we threaded our way into Telegraph Harbour on Thetis Island, where two double-ended ferries regularly visit. They’re designed to get in and out of a terminal quickly; when they back out, they spin around, and it’s difficult to tell where they’re bound. I can only compare watching this to how a matador must feel when a bull stares him down. Olé and get out of the way.

The spring ebb compelled us to run at idle speed into Telegraph Harbour, then to Thetis Island Marina, where we took a just-deep-enough slip. Off we went to stretch our legs, and we came to one of the many “drying passes” in these islands. Known as “The Cut,” it serves as a risky shortcut between Thetis and Penelakut islands. We watched a small sailboat run aground trying to get through, and decided to cruise the long way when it was time for us to leave. Back at the marina’s pub, we scarfed down big bowls of clam chowder and enjoyed the warmth of a wood-burning stove, all with a great view of the boat traffic.

An incendiary sunset lit up the sky and harbor that night with radiant bands of yellow, orange and red, all burning away at the stratified clouds like a prairie wildfire. A wedge of frantic geese flew over the docks, and an owl awakened nearby, hooting its warning. It was one of those forever moments that’s all too short; within a minute, a long gray line advanced downward, pushing the colors beneath the horizon until nothing remained but a bloody glow between distant mountains. This is why I sail: It puts ordinary people like me in a position to witness the extraordinary.

Underway the next morning, we turned southeast and realized that the wind had swung to the south. Oh well, at least the skies were blue and the tide was going our way. The green mountains rose sharply, soon to be covered with snow. 

The Bavaria’s Volvo hummed contentedly. We found it to be a solid cruising yacht, albeit plastered everywhere with German imperatives such as: abwindstarke 6 sind alle kabinen-fenster zu schlieBen. That is:“In wind force 6, all cabin windows are to be closed.” Who says high school language classes don’t come in handy later in life? 

We took a sharp right at Southey Point and crossed tracks with a bulk carrier. Quickly, we steered to the side to let it pass, but a distant sailboat remained in its path. The five stentorian blasts of the ship had its crew scurrying aside. 

The small anchorage at Retreat Cove was nearby, but we carried on for the long western approach to Montague Harbour and the dock at Marine Provincial Park. From there, it was off to town to catch the bus to the famous Hummingbird Pub. Sadly, it had just closed for the season. In fact, most of the village had called it quits for the year. Back in the boat’s cockpit, as the harvest moon rose over the many anchor lights, Dan and I reminisced of days gone by in Ohio. We heard the plaintive cry of a loon. Could there be a better end to any day?

The sun rose and, despite the 44-degree temperature, it was another winner of a day with nary a cloud in the sky nor a soul moving in the anchorage. After dancing with several leviathan ferries and making the pass west of Prevost Island, we entered a massive fog bank. Dan was at the helm and I was at the bow, bleating the foghorn. Of the frequent fogs here, Blanchett wrote: “It would roll down the open channels in great round masses—­hesitate for an island, and then roll over it and on. It would fill up all the bays—searching and exploring.”

We made the turn into Bedwell Harbour and grabbed one of the many moorings at Beaumont Marine Park as the fog receded just above the tip of our mast. A hike up Mount Norman proved a lot more exercise than we’d anticipated; it was surprising that after two hours in the woods, we saw not a single critter. 

With the sun well across the yardarm, it was time for sundowners and a good meal. We zipped across the harbor to Poets Cove Resort & Spa, which was named, we were told, for the many marriage proposals that happened there. Dinner at the bar was awesome, enhanced by a spirited conversation with some patrons and the barkeeper about what makes Canadian football better than American. (Three downs instead of four? Are they kidding?)

Really, I’m not making this up: The sun rose again to a cool, clear morning without a breath of wind. Boats around us were frozen in place, clearly reflected in the water.

A seal snorted nearby, no doubt looking for a fish breakfast. Ours would be avocado toast with eggs and java. We let loose the mooring and were bound for Lyall Harbour on Saturna Island. We crept through the pass between Pender Island and Blunden Islet: very narrow, very nerve-wracking. Our Lady of Blessed Navionics got us through, with 20 feet to spare.

Later, Dan called down from the wheel: “Hey, bro, this ­powerboat is gonna hit us. What should I do?” 

I quickly explained the basic rules of the road, which in a crossing situation can be summed up as: When he’s right, you’re wrong. The fishing boat was crossing our path from the left side. “So we’re the stand-on ­vessel?” Dan asked. “Precisely,” I ­answered. “But let’s be ready to circle around his stern if he doesn’t know this too.”

We rounded the tip of Saturna and squeezed ­into the public wharf at Lyall Harbour. The cruising guide talked of a bike-rental shop nearby, but it had recently gone out of business. No car rentals either. We had our feet, but these islands are big; next time, we’ll bring bikes.

A hike eastward for a few clicks brought us to Saturna General Store & Freight, where we made our last grocery purchases of the cruise. My cash was getting low. Banks that provide foreign exchange are few and far between in the Gulf Islands, but major credit cards are accepted everywhere. And most places accepted our US cash.

Back at the wharf, we bought tasty bread from Vibrational Café and learned that it was closing for the season in a few days. As the moon peeked out from the distant trees, we enjoyed dinner from the deck of Saturna Lighthouse Pub and watched the last floatplane and ferry head off into the gloaming.

We were underway again on another no-wind morning and spotted basking seals on Saturna Beach, then motored past the dreadfully named Murder Point and wiggled through the many tidal rips along the international border south of Moresby Island. At Portland Island, we made a final ride to the beach for a hike, then called it a week.

It was time to refuel and then deposit Immaterial Girl back in its slip, where it would be cleaned and turned over to another party. Dan and I tied up and fist-bumped, happy for the great week together and all the special places we had visited. 

And then we walked away from one of the best sailing grounds on the continent.

The post Islands in the Strait: Sailing Canada’s Gulf Isles appeared first on Cruising World.

It was shaping up to be ­another postcard-perfect day at anchor in Thailand. My husband, Jamie, was working on deck aboard our Stevens 47, Totem, when he let out a shout that made everyone’s spine snap straight.

“Hey! Hey! Look out!”

A bareboat charter catamaran was bearing down on us—fast—and the people aboard were too busy laughing and posing for selfies to notice. The skipper finally looked up from his phone just in time to veer away, clearing our anchor chain by maybe 10 feet. 

“I saw ya, mate,” he called out. 

Sure you did.

For anyone who dreams of cruising, chartering can be a brilliant first step. But the gap between dream and disaster can be alarmingly narrow. Done right, bareboating is a confidence-building adventure. Done wrong, it can be a deal-breaker.

If you’re thinking of chartering as a stepping stone to life afloat, here’s how to get it right, from the skills you’ll need to the surprises you’ll want to avoid.

Build the Right Skills 

A successful charter doesn’t just depend on your spirit of adventure. It also relies on your ability to handle the fundamentals. 

Even seasoned sailors can get tripped up when stepping aboard a vessel that’s significantly different from what they’re used to handling. Twin engines, catamaran maneuvering, electric winches, a ­heavier displacement hull—all these variables affect everything from docking to anchoring to systems management.

“If you’ve been off the water for a while, or if your experience has all been in smaller or simpler boats, consider brushing up before your trip,” says Tracy Sarich, owner of Voyage Makers Coastal Adventures in British Columbia, Canada. “One of the most common issues we see is a gap in skills that becomes clear only once a client is already at the dock. That’s hard on everyone.”

To avoid that last-minute scramble, consider taking a refresher or liveaboard course with American Sailing or the Royal Yachting Association, or through the charter base. Many companies offer training designed to mirror real-world charter conditions, often using the same types of boats you’ll be renting. Not only does this kind of refresher course sharpen your skills, but it also builds confidence and reduces anxiety for you and your crew.

“Research your charter company’s requirements early,” Sarich says. “Then plan your prep accordingly. We tailor training to match both the boat and the cruising area, so charterers feel ready when it’s time to go.”

The more solid your foundation, the more fun you’ll have—and the more likely you’ll be planning the next adventure before this one’s even over.

Be Honest 

It’s important to recognize that while your sailing skills might be top-notch in your home waters and familiar conditions, those skills might not translate seamlessly to a new charter-base location. Charter bases often vet those skills carefully—especially in areas with more-complex navigation dynamics.

Charter guests can get frustrated when required to sail with a checkout skipper. “Do they think I’m not experienced?” “Did they not believe my sailing résumé?” In reality, it’s not about mistrust—it’s about setting you up for a safe and enjoyable trip.

“Charter companies want your experience to be a positive one,” says Capt. Margaret Pommert, a veteran sailing instructor who conducts checkout orientations for charters in Puget Sound. “They know their boats and waters better than anyone, and they’ve seen what can go wrong.”

A checkout skipper’s role is to familiarize guests with the vessel and local conditions, ensuring comfort with handling, docking and onboard systems. At the end of the process, the skipper must determine whether the guest can safely manage the boat—and their crew.

Even seasoned sailors can be caught off guard by unfamiliar waters. Deepwater Puget Sound sailors might run aground in Florida’s shallows. A salty Southern California sailor might struggle when the “wind machine” kicks in on a summer afternoon in San Francisco Bay.

Pommert remembers a Chesapeake Bay sailor—and hopeful family cruiser—who was planning a Puget Sound charter with his anxious wife and young children. He ­proudly explained that he had interpreted the local tide tables and intended to sail through Deception Pass on a max ebb current. Recognizing this as a recipe for disaster, Pommert gently explained the danger of his plan and introduced the concept of a tidal gate. Together, they reworked the itinerary.

A month later, the family bought a sailboat. Six months after that, his wife enrolled in one of Pommert’s courses.

A good checkout skipper is a mentor and partner. They help you build on your strengths, identify knowledge gaps, and ensure that your charter is a success. It’s a rare ­opportunity to grow; embrace it.

Know the Systems

Even experienced sailors can find themselves flustered on a charter boat. The systems might be unfamiliar, the layout unexpected and the interface—bonjour, French chart plotter—less than intuitive. What you think of as basic sailing knowledge might not prepare you for the living ­systems that make a boat feel like a functioning home, even for a week.

On a charter, you might be managing a watermaker, monitoring battery-charge levels, or operating a macerator pump for the heads. These are things you might never touch on a daysailer or even your own coastal cruiser. Mismanaging these systems can lead to discomfort, stress and safety issues.

“In-mast furling systems, for example, are very common on charter sailboats,” says Tracy Sarich of The Voyage Makers. “Clients who say they know how to use them—because they’ve watched a YouTube video—are often the ones calling on day one when something goes wrong. These issues could be avoided if they gave themselves a little more time for discussion at the dock.”

Before you board, ask for a list of the boat’s equipment. Familiarize yourself with anything unfamiliar. Charter ­companies might be able to provide videos or manuals. If not, a little digging online—­especially on YouTube—can go a long way. Make a checklist of key systems that you want to understand: How do you monitor tank levels? Where are the breaker panels? How does the autopilot engage? And, yes, how do you flush the toilet?

Even details such as PFD comfort, dinghy operation and stove ignition can feel like small wins if you take the time to get familiar up front. The orientation provided by the charter base is valuable, but it’s not always enough, especially if you arrive rushed or distracted. A little homework before you go can make your entire week more enjoyable. 

Research and ­Prepare

Sailing in a new place can be thrilling—but also deceptive. It’s easy to assume that your sailing skills will transfer ­seamlessly. In reality, every destination has its quirks, risks and local ­knowledge. Maybe it’s the swift tidal currents and narrow passes of the San Juans, or the sharp katabatic winds that come screaming down Greek hillsides in the Med. Even the most seasoned sailors can be caught off guard when they underestimate the local conditions.

Nothing beats advanced planning and asking questions of your charter company ahead of time so that you can discuss your plan with a local expert upon arrival.

“Most accidents occur on charter boats because clients have overestimated their ability to read the conditions in a new area,” Sarich says.

She appreciates when guests take time before their trip—and during that first day of orientation with The Voyage Makers—to plan and prepare, making their vacation more relaxing. It can also save money, especially when security ­deposits are at stake.

Lara Ortiz runs Ocean Adventure Cat charters with her husband, Jason Decker, and has seen both sides of the coin when it comes to research.

“We met some nonmariners on a dive trip in Borneo who were super-interested in sharing a bareboat with us one day,” she says. “They joined us in St. Lucia, loved it, and went home to Germany to earn their sailing certifications. A year and a half later, they invited us on a sailing trip in Croatia, with Jason as the backup skipper.”

On that trip, their friend—the first-time charter skipper with an engineer’s mindset—brought along a 3-inch binder with divider tabs. It included detailed information on the cruising grounds, potential itineraries, summaries of each destination and port, anchorage and marina chart screenshots, explanations of local weather patterns, guidance on areas to avoid and how to identify risk factors, and diagrams of line and rudder configurations for different docking conditions.

Ortiz and Decker were the only experienced sailors aboard, but each day, their friend—the new skipper—would review ­relevant maneuvers with the crew and assign clear roles.

“He maintained great communication during sailing, docking and anchoring,” Ortiz says. “Preparation paid off, and the trip was a rousing success.”

Be Realistic

One of the most common causes of charter disappointment is an overstuffed itinerary. It’s tempting, especially on your first trip, to try to check off every beach, bar and snorkeling spot that you flagged in the guidebook. But cramming too many destinations into too few days almost always backfires. You spend your week rushing between anchorages, eyes on the clock, powering through squalls or skipping swims—all just to stay on schedule. 

The problem is mindset: We come from lives governed by fixed calendars and concrete deadlines, where a change in the weather just means packing an umbrella. But sailing doesn’t work like that. Weather shifts, boats need attention, and sometimes the best-laid plans give way to the perfect cove you didn’t expect to fall in love with.

Give yourself time, especially on day one. Settle in, get to know the boat, and slow your roll. Marla Hedman, a captain with The Voyage Makers, recalls a charter crew who arrived late, eager to cast off and make their first anchorage before sunset. In their haste, groceries were hurried aboard, the boat briefing was rushed, and they motored out without properly checking systems. 

Later, when they went to raise the main, the electric winch jammed—and they kept pressing the button. Pop. Pop. Pop. The halyard, still routed through the lifelines, ripped stanchions from the deck one by one. Their charter ended ­before it really began.

The lesson? Prioritize ease over ambition. Aim for fewer destinations, with more time at each. Let the weather and your mood guide your course. Savor the unplanned layover, the lingering lunch or the unexpected sunset in a bay you didn’t even mean to stop in. 

When you make room for spontaneity, that’s when magic tends to happen.

Bring Perspective

Your mindset is one of the most important pieces of charter prep—more than any checklist or chart-plotter app. 

Charter boats get used hard. Systems wear, cushions fade, things break. The air conditioning might groan in protest, the dinghy might have a sticky outboard, and the watermaker might be out of commission entirely. None of these situations is ideal, but none of them need to ruin your trip.

One of our coaching clients, fresh back from a weeklong charter in the BVI, told us: “It wasn’t exactly as advertised. Our boat was supposed to have a watermaker, but it wasn’t working. Yet for one week in the BVI, it was easy enough for us to manage on board.” 

His takeaway? A little flexibility and problem-solving made the trip feel more like an adventure and less like a resort stay. That’s actually pretty close to real cruising, where “something always needs fixing” is less a complaint than a mantra. If you treat minor hiccups as part of the story, then you’re already thinking like a cruiser.

There’s also another way to bring perspective: If you’re chartering and curious about the liveaboard lifestyle, look around the anchorage. Cruisers are easy to spot. They typically have laundry flapping from the lifelines, an array of solar panels, jerries lashed to the rail, and someone in the ­cockpit elbow-deep in an electrical panel or a winch servicing. Go say hi. Most of us remember exactly what it was like to be cruiser-curious, and we’re ­often more than happy to swap stories or offer a quick tour.

Just maybe don’t drop your anchor right on top of theirs.

Pregame Like a Cruiser 

If you’re treating your charter as a trial run for future cruising life, don’t wait until you’re aboard to start thinking like a full-time ­sailor. Use the planning phase to build real-world skills and gain confidence with the tools that cruisers rely on daily. Try this ­four-step checklist before you even book your flight.

Practice With Charting Software: Install a navigation app such as Navionics or Aqua Map on a tablet. Practice route planning manually to get familiar with chart overlays, depth contours, and hazard markers. No auto-routing.

Track Weather: Download a robust marine forecasting app such as PredictWind. Ask your charter base which forecast models they trust most for the local area, then begin following them days or weeks in advance. You’ll get a sense of how patterns evolve in your  destination.

Scout Anchorages With Cruiser Intel: Platforms such as Noforeignland let you explore anchorage reviews and track real cruisers’ movements. Study the footprints of others to get a sense of practical, comfortable routes, as well as ones to avoid.

Understand Local Phenomena: GRIB files don’t tell the full story. Learn about region-specific weather quirks such as katabatic winds in the Med, chubascos in the Sea of Cortez, and squalls that funnel between islands. Knowing what’s likely to catch you off guard helps you stay ahead of the curve.

The post How to Bareboat Charter Like a Cruiser appeared first on Cruising World.

My wife, Kati, and I had built a small and profitable business in Nottingham, England. We decided to take a well-earned six-week vacation in Greece during our two young daughters’ school holidays. We ­rented an RV to travel at our own pace, stopping wherever and ­whenever we wanted. When we arrived in Athens, we chartered a Coronado 35 ketch for a week and sailed around the stunning Peloponnese, crewed by two American lads because we had never sailed before.

Inspired by this experience, we sold our business, house and furniture, and bought a 40-foot Endurance ketch, which we named Tranquility Base in honor of the first American moon landing. With our children aboard, we set sail for the Mediterranean on what was meant to be a two-year ­sabbatical—and we ended up staying for seven. 

After the first year, we ­realized that we needed to start earning again to sustain our nomadic lifestyle. What better way than to use our beautiful boat to charter?

Charter sailing was in its infancy in the Mediterranean back then, and I signed on with a British charter agency targeting novice sailors who were looking to learn in the sun with a captain and cook. That’s when things started to get interesting.

Bookings Begin

Our first guests were an American couple traveling through Europe who ­wanted to see if they liked sailing. Our boat was perfect for them: ­comfortable, manageable and well-equipped for short coastal trips.

One afternoon while we were anchored in a quiet bay, the wife decided to go for a swim. For reasons of modesty, she wore a wool poncho over her swimsuit. It quickly became waterlogged. The weight of the soaked fabric dragged her down. She managed to shed the poncho and grab hold of a floating line we had over the side, but she didn’t have the strength to climb back aboard.

I couldn’t lift her out of the water, so I rigged the main boom with a snatch block and passed a line beneath her arms to form a sling. Kati lowered the lifelines between two stanchions as I hoisted the guest up and over the rail. She came aboard safely—albeit ­awkwardly—landing on deck like a beached fish.

It was an unglamorous start to our chartering career, but it taught us an early and valuable lesson: Be ready for anything.

The One-Armed Sailor

On another charter, we hosted a couple whose husband had only one arm. He was considering buying a sailboat and wanted to find out if he could handle things on his own. Since we’d advertised that our ketch was rigged for shorthanded sailing, he saw it as a good test platform.

Our self-tailing electric winches were key to making sailhandling manageable for him. But at the time, portable electric winch handles—now common and helpful—weren’t yet available. He managed admirably under calm conditions and found ways to adapt, but it was clear that sailing solo or in rough weather would present serious challenges.

In the end, he chose to buy a powerboat—probably the wisest and safest option for his needs. I’ve often thought about that experience and whether someone with a similar limitation could truly handle a sailboat safely without a capable crew, ­especially in an emergency.

The Drunks

While in Gibraltar, I accepted a charter from five men who, coincidentally, were also from our hometown of Nottingham. From the outset, they were more interested in partying than sailing. Sensing how the week might unfold, Kati made the smart decision to stay ashore with our daughters in a rented chalet. I stayed aboard to skipper the boat and quickly came to regret it.

The group’s main goal was drinking and meeting women. They also wanted to sail to Tangier, Morocco, about 40 miles across the Strait of Gibraltar. I warned them that the Strait was busy with commercial traffic and that Morocco had a different cultural attitude toward gender and public behavior, especially where Western tourists were concerned. They didn’t care.

Once in Tangier, they met three local sisters who invited them back to their apartment. What the men didn’t realize was that the women still lived at home. The evening ended not with a party, but instead with tea served under the strict supervision of their father, who told them that any infidel who laid a hand on one of his daughters would lose his head. The scimitar mounted above the fireplace suggested that he meant it.

On the sail back to Gibraltar, one of the men wore a kandura​—a long, traditional robe—that got caught in the sheet winch while we were tacking. He was yanked to his knees and tangled in the lines while his friends laughed. I had to reroute another line carefully to free him, a process that took a good amount of time and effort.

It was a charter I was glad to see end, and a firm reminder that good seamanship sometimes includes managing difficult personalities as much as handling sails.

Some Caught the Sailing Bug

Not all guests were challenging. In fact, some became longtime friends, and a few bought their own boats. One family with two young daughters chartered with us near Saint-Tropez in the South of France. We spent several days sailing around Île de Porquerolles until, unexpectedly, I was told we needed to return immediately to Port Grimaud. The wife feared she was having a miscarriage. I hadn’t even known she was pregnant. Thankfully, they had good insurance and were flown back to England on a medical flight. She received prompt care.

A few years later, that same family reappeared in Gibraltar, this time arriving in an old motorboat after navigating the European canal system. They had become skilled sailors, owning a fine boat and even undertaking deliveries across Europe.

Their journey was a rewarding reminder that some charter guests truly embrace the lifestyle, growing from nervous beginners into confident boat owners and sailors.

The Rum Deal

When we were based in Gibraltar, the British Admiralty finally ended the centuries-old practice of issuing a daily rum ration to sailors—a tradition dating to 1740. This change became a windfall for Tranquility Base. Surplus rum was sold ­locally in Gibraltar for about 10 GIP per gallon (about $13.58 US), still bottled in the original pot demijohns.

I always stocked up with a couple of gallons before heading to the Mediterranean. At dinner, we served guests neat rum and grog—the classic British naval mix of rum diluted with water—keeping alive a bit of maritime heritage.

We realized that we needed to start ­earning again to sustain our nomadic ­lifestyle. What better way than to use our beautiful boat to charter?

The raw rum was a strong, warming drink that few could handle in quantity. While the traditional naval “tot” was half a pint twice daily, most guests barely managed a couple of neat servings before feeling the effects. It was also a reliable way to encourage early bedtimes in the afternoon, which, for a skipper, was often just as ­welcome as the drink itself.

Heads and ­Headaches

Our boat had just one Baby Blake marine toilet, and it required precise instructions to operate correctly. Guests had to open the valves and pump the lever in the right sequence to avoid unpleasant consequences.

I often ended up emptying the toilet after someone got it wrong, and it wasn’t uncommon to hear a startled shriek from the head when a guest struggled. On rare occasions, I even had to put on rubber gloves to retrieve items that had fallen into the bowl.

A single toilet is far from ideal for a charter boat, especially with multiple guests. That’s why on our current boat, we upgraded to two electric toilets. They are much easier to use and far less likely to cause trouble.

Seasickness: An Inevitable ­Challenge

Mal de mer was a common issue among guests who had never been on a small boat before. We always advised them to take motion sickness tablets before boarding, just in case, but sometimes even that wasn’t enough.

When nausea hit, the best we could do was provide a bucket and discreetly dispose of the contents later. Most guests got their sea legs within a day or two, but occasionally we had to remain tied up in a marina for several days while some guests adjusted to life aboard.

Patience and preparation were key, for the guests and crew alike.

Hot-Water Hustle

Keeping enough hot water for daily showers by four or five people was always a challenge aboard our boat. When we docked in port, we could plug into shore power and easily heat the water. But anchored in secluded coves, we had to rely on the engine’s heat or our portable Honda generator to warm about 15 gallons of water. Our options were noisy and annoying for a peaceful anchorage.

On sunny days, I sometimes hung a plastic bag from the mast, fitted with a shower head. The sun would heat the water inside, providing a ­simple solar shower. The catch? After ­rinsing off, guests needed to jump into the sea to wash away the soap and cool down. Children enjoyed this, but ­many adults were less enthusiastic about the swim.

Balearic Bliss

Some of our most enjoyable charters took place in Spain’s Balearic Islands, particularly Ibiza and Mallorca, where we ran day charters for groups of young vacationers. We’d pick them up from a beach near their hotel and sail to a nearby island or sandy cove.

The days were filled with swimming, snorkeling and relaxing drinks at a local bar. Many guests would nap on deck during the leisurely return sail, soaking up the sun and sea breeze.

We repeated this routine for several days each summer. It not only brought us great memories, but it also made a valuable ­contribution to our boat fund.

From Buckets to Bathtubs

All of this happened in the ­early days of sailboat chartering, when the sea felt wide open and the rules were few. Anchoring was easy, paperwork was ­minimal, and most of us were figuring things out as we went. It was a simpler time: rugged, rewarding, and full of surprises.

Today, chartering looks ­different. You can hire a ­skipper for just a few days, or even for a single afternoon, to sail, cook dinner and head home before sunset. Boats have become floating homes with every ­comfort imaginable.

Our current 50-foot ­schooner has twin air conditioners, a washer/dryer, a deep freezer, two heads with electric toilets and showers, and a full-size bathtub with jets. It’s a far cry from our early setup with one hand-pump head and a bucket on deck.

And yet, no matter how far the gear and the business have come, some things haven’t changed at all. The sea still finds ways to keep us humble. 

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St. Thomas, U.S. Virgin Islands — Tensions are rising between neighboring territories in the Virgin Islands as the Virgin Islands Professional Charter Association (VIPCA) urges the U.S. Virgin Islands government to implement reciprocal licensing measures in response to recent fee increases by the British Virgin Islands.

The controversy stems from a decision by BVI authorities to impose significantly higher licensing fees on U.S.-based vessels conducting charter business in BVI waters. The new measures, part of the Commercial Recreational Vessels Licensing (Amendment) Act, 2025, have sparked concern among U.S. Virgin Islands operators who argue that the increased costs are punitive and threaten the regional charter industry’s cooperative foundation.

In a public statement, VIPCA described the BVI’s move as “short-sighted and unfortunate,” claiming that the new regulations place an unfair burden on USVI-based charter vessels. In response, the organization is calling on the USVI government to take action by enforcing existing laws more rigorously and implementing reciprocal fees and compliance requirements for BVI-based vessels entering USVI waters.

Concerns Over Economic Impact

VIPCA points to the size and significance of the marine tourism industry in the USVI, which it says supports more than 5,000 jobs and contributes over $166 million annually to the local economy. The association warns that without intervention, businesses may be forced to relocate to the BVI, creating ripple effects across a wide network of supporting industries including marinas, mechanics, grocery stores, restaurants, and hospitality services.

“The USVI charter industry is at risk,” VIPCA said. “Every vessel that relocates to the BVI or day charter business that shuts down means not just the loss of that operation, but impacts across the entire maritime supply chain.”

The association has outlined several steps it believes the USVI government should take immediately, including:

• Imposing matching licensing fees and access restrictions on BVI-based charter vessels
  
• Requiring proof of U.S. customs clearance for all foreign vessels prior to passenger embarkation or disembarkation
  
• Enforcing compliance with U.S. Coast Guard crew credentialing and vessel safety requirements
  
• Mandating the use of the U.S. eNOA/D arrival and departure system

A Call for Cooperation—or Competition?

While the BVI government has not publicly responded to VIPCA’s latest statements, officials there have defended the fee increases as part of broader efforts to strengthen oversight and regulatory compliance within their waters. The BVI’s charter sector has also grown significantly in recent years, with local stakeholders pushing for policies that ensure more direct economic benefit to the territory.

Some in the region worry that a tit-for-tat regulatory approach may damage long-standing cross-border tourism ties. For decades, charter boats have freely cruised between the USVI and BVI, offering visitors seamless itineraries that span both territories.

VIPCA, while advocating for reciprocity, also emphasized its preference for a collaborative future. The organization has proposed the concept of a “Greater Virgin Islands Sailing Zone”—a joint initiative between the BVI and USVI to streamline regulations and foster shared maritime prosperity. But for now, VIPCA says, the BVI’s decision to act unilaterally has forced the USVI to respond in kind.

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