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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Sint Maarten’s next generation of sailors delivered a standout performance at the 2025 Caribbean Dinghy Championship, earning second place overall in the Nations Cup and podiums in every fleet they entered. The event was hosted by Antigua Yacht Club from October 24–26.

Six sailors represented the Sint Maarten Yacht Club across Optimist, Topper Fusion, and ILCA fleets, and their consistency put the team just behind host nation Antigua and ahead of other regional programs.

Results

• 1st Optimist: Nathan Sheppard
• 1st Topper Fusion (Double-Handed): Oskar Jarrett Versteegden and Adilyn Treadwell, with Paola Lapierre crewing on Day 1
• 3rd ILCA 4: Harper Treadwell
• 3rd ILCA 6: Massimo Lapierre

“This year’s results show how hard our young sailors have worked,” said SMYC Racing Coach Sam Peeks. “We are so proud of how they represented Sint Maarten not just through their results, but also through their great attitude and sportsmanship.”

In true island-sailor style, the team made an offshore passage to the regatta as well, sailing from Sint Maarten to Antigua aboard a monohull. The trip served as both training and team bonding ahead of the three-day competition.

The Caribbean Dinghy Championship is organized by the Caribbean Sailing Association and brings youth competitors together from across the region for a mix of national pride and top-level dinghy racing.

For more on the Sint Maarten Yacht Club’s programs, visit smyc.com.

Building the Next Wave of Caribbean Sailors

Youth sailing programs across the Caribbean continue to grow, with island clubs investing in coaching, fleet development, and regional racing opportunities. The Sint Maarten Yacht Club, founded in 1980, runs an active junior program aimed at building seamanship, teamwork, and confidence on the water.

From Optimists to ILCA dinghies, young sailors across the region are gaining offshore experience as well, often through inter-island passages to major events. With regional regattas like the CDC and iconic events such as the St. Maarten Heineken Regatta in their backyard, Caribbean sailors are finding a clear pathway from junior fleets to international racing.

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The 2nd annual Great Bay Beach & Boardwalk Jamboree will return to Philipsburg, Sint Maarten, on Saturday, January 31, 2026, bringing together sailors, locals, and visitors for a full afternoon of racing and island festivities.

The waterfront celebration will center around Great Bay, where the DIAM 24 fleet will take to the water for fast-paced, one-design racing close to shore. Spectators can enjoy front-row viewing at the Dutch Blonde Beach Bar from noon to 3 p.m., with live broadcasting, island music, and cold drinks on tap.

From 3 to 5:30 p.m., the focus shifts to friendly competition ashore with beach games including volleyball, tug of war, and cornhole. This year’s events and evening entertainment will be hosted by Seaview Beach Hotel, a longtime Philipsburg landmark that first opened in 1947. The boutique beachfront property will host prize giving and an evening celebration with happy hour specials, music, and dancing.

“Seaview’s location and hospitality make it the perfect home base for both racers and spectators,” event organizers said. “It’s a natural fit for the fun and energy of the Jamboree.”

Guests can enjoy Seaview’s poolside cabanas, on-site restaurants, and a convenient nearby market for provisioning before Sunday’s events. The hotel is also offering a special promotion that includes breakfast for Caribbean Multihull Challenge participants and Jamboree guests.

Now in its second year, the Great Bay Beach & Boardwalk Jamboree has quickly become a highlight of the Caribbean Multihull Challenge, celebrating sailing culture while connecting visiting racers with Sint Maarten’s local community and lively beach scene.For more details and registration information, visit caribbeanmultihullchallenge.com.

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Entries are officially open for one of the Caribbean’s premier sailing events, the 2026 St. Thomas International Regatta (STIR), set for April 3–5, 2026, at the St. Thomas Yacht Club. The event will be preceded by the popular Round the Rocks Race on April 2, which takes competitors on a scenic and tactical circumnavigation of nearby St. John.

Now in its 52nd year, STIR is known for blending high-caliber competition with the easygoing spirit of island hospitality. Racers from across the Caribbean, North America, and Europe gather each spring to compete in one of the region’s most scenic and welcoming venues.

“Sailors can look forward to the best in handicap and one-design racing on round-the-islands and round-the-buoy courses professionally set by some of the best race management in the world,” said co-director Pat Bailey, who organizes the event alongside Greer Scholes. “In 2026, we will host the second annual IC24 Caribbean Championship as part of STIR. This top-quality racing we match with friendliness, hospitality, and an equally popular club-run event ashore. As we like to say, ‘We love it here,’ and we invite you to enter now and race with us in March.”

STIR 2026 will feature racing under CSA (Caribbean Sailing Association), IRC, ORC, and Multihull handicaps, with divisions for Racing, Cruising, CSA Bareboat, and One Design fleets, including IC24s, Diam 24s, Hobie Waves, and other eligible classes 19 feet or longer.

The one-stop venue at the St. Thomas Yacht Club provides easy logistics and an unmatched Caribbean beachfront atmosphere. Competitors and guests can expect the club’s signature mix of precision race management, lively social events, and a community of sailors who return year after year.

Early entry discounts are available through January 31, 2026, with a $170 registration fee for all classes. From February 1 to April 1, entry fees rise to $340 for most classes, $240 for IC24s and Diam 24s, and $150 for Hobie Waves.

Whether you’re a pro campaigner or a weekend sailor ready to test your mettle in turquoise seas, the 2026 St. Thomas International Regatta promises top-tier racing and the warm welcome that has long defined sailing in the Virgin Islands.

For details and registration, visit yachtscoring.com/emenu/50483.

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US Sailing has announced a new partnership with The Windjammer Way, a group dedicated to reviving the era of classic windjammer cruising by restoring and operating historic vessels throughout the Caribbean.

The collaboration aims to connect sailing’s heritage with its future. Together, the organizations will develop opportunities for US Sailing members, create content to celebrate sailing culture, and organize events that highlight traditional seamanship for wider audiences.

“Partnering with The Windjammer Way represents a celebration of sailing’s roots and future,” said Charlie Enright, CEO of US Sailing. “Their mission to restore historic vessels and offer them to the world resonates with our commitment to legacy and connection through the water.”

At the heart of the effort is the 102-year-old S/V Mandalay, now undergoing a complete restoration. Originally built in 1923 as a luxury yacht for financier E.F. Hutton and his wife, cereal heiress Marjorie Merriweather Post, the vessel has lived many lives. She served as a research ship for Columbia University, logging more than a million nautical miles and contributing to the theory of continental drift, before finding a long career in Caribbean charter service.

Now, The Windjammer Way is giving Mandalay a new chapter. Craftsmen are rebuilding her steel hull, restoring rigging and preserving original design features while outfitting the vessel with modern safety systems. Completion is planned for spring 2026.

“The overwhelming response to our crowdfunding efforts demonstrates how much people value authentic sailing experiences and maritime preservation,” said Charles J. Kropke, CEO of The Windjammer Way. “Partnering with US Sailing elevates our mission and creates exciting possibilities for sharing our restored vessels with sailing enthusiasts at every level.”

Mandalay is set to become the flagship of a broader fleet of restored windjammers that will sail to secluded anchorages and off-the-beaten-path harbors across the Caribbean. The long-term vision is to combine heritage, community, and adventure by bringing sailors aboard ships that embody the golden age of sail.

For US Sailing, the partnership represents an extension of its mission to grow participation in the sport while honoring its traditions. For The Windjammer Way, it ensures that historic vessels remain not just museum pieces but working ships, continuing to inspire new generations of sailors.

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Looking back on my racing IC24s in the windswept waters off St. Thomas in the US Virgin Islands this past spring, it’s difficult to say which of my bone-headed mishaps stung most. Yes, it might’ve been the moment the spinnaker pole went totally astray during a hectic kite drop and crowned me upside the cranium. I hadn’t seen such stars since my old college-football days, laid out reaching for a pass over the middle. 

Then again, there was the instant when we jibed in a barrel of breeze and, in an attempt to gracefully swing the mainsheet from port to starboard, I forgot to let go. That one left me flat on my back in the cockpit with my wind knocked out. Woof. 

Or was it re-tweaking my testy rotator cuff grinding a winch after a freak injury just a couple of months before? The one that elicited this observation from my physical therapist when I’d told him of my sailing plans: “I don’t think that’s such a great idea.”

So much pain. So hard to choose. So different from what I’d envisioned.

After all, when the plan had been hatched the previous summer, it was a glorious one indeed. I’ve been racing J/24s off Newport, Rhode Island, with old pals Ian Scott and Dave Reed for some four decades now. Every so often, we load Ian’s Crack O’ Noon onto the trailer to compete in a North American or World Championship event. This was a different out-of-town exercise altogether: to charter an IC24 for a week to sail the St. Thomas Yacht Club’s annual International Regatta. 

The IC24s are a Caribbean phenomenon. They’re modified J/24s that have been refitted and tamped down; the revamped cockpit means no hiking out, and a blade jib has replaced the big genoa to depower the sail plan. We’re not exactly the world’s flashiest J/24 sailors, but we’ve logged some serious miles. We reckoned that mastering an IC24 would be easy-peasy. Shorts and T-shirts on the racecourse, plenty of cold beers after. Who wouldn’t want to be us?

This rather cavalier attitude was reinforced on the practice day before the main event commenced, in about 12 to 15 knots of wafting Caribbean breeze, as we spun the boat around the buoys without drama. Afterward, however, while sipping brews on the yacht-club lawn, there were murmurs about the impending conditions. It was apparently going to get windy. It didn’t quite occur to me that if the locals were concerned, I should be as well.

The next morning, the big easterly trades—belting in at a solid 25 knots, gusting higher—and a harsh dose of reality arrived at exactly the same time.

How did it all go sideways? Let us count the ways. Dave had recruited his son, Tim, to join us, but we were one of the few ­four-man crews in the 21-boat fleet. We didn’t think that sailing without a fifth crewman would handicap us, but we were constantly on our ear without the additional human ballast (guilty of being not only overconfident, but also overpowered). 

Then, things began to break: the boom vang and the base of our mainsheet swivel block being the most egregious gear failures. We compounded the damage with some dumb, unforced errors: a blown jibe that resulted in a spinnaker wrapped as tightly as possible around the headstay, a jib halyard that skied to the mast head when the shackle somehow came undone (we’d even taped it). 

Meanwhile, the races kept on coming, fast and furious, five a day over three days, bang-bang. And the wind? It never faltered. As we nursed the boat around the buoys, our results plummeted. We slowly, inexorably inched our way toward the back of the fleet. It was humbling. Thank heavens the beer remained chilled. 

In the aftermath, there was time for reflection. Not for the first time, I was reminded that I’m not getting any younger, and it even occurred to me that I might be getting a little long in the tooth for this particular game. You can still sail without racing, right?

Then again, I’d survived. Ian called a few weeks later to say that it was time to get Crack O’ Noon back in the water for the season ahead. Was I in?

Was I ever. 

Herb McCormick is a CW editor-at-large.

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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. 

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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.

As fall approaches, Horizon Yacht Charters is embracing a new phase of its evolution—digitally, operationally and geographically. With a fresh suite of websites and a few high-profile additions to its fleet, the Caribbean-based company is quietly sharpening its edge in a competitive charter landscape, all without losing the hands-on, local service that has long been central to its identity.

At the center of this update is a new set of websites. In the coming months, the company will roll out separate sites for its various offerings, including bareboat yacht charters, sailing school, luxury crewed yachts and yacht sales. These sites have been designed to better reflect the distinct arms of Horizon’s business. Most significantly, the charter site will feature a new real-time booking system, giving guests the ability to secure their dates without waiting on office hours in the islands. It’s a logistical step forward, but it is also one made with care.

• Established in 1998 in the British Virgin Islands and with a base in St Vincent & the Grenadines, Horizon has historically been characterized by its penchant for person-to-person service. Horizon Co-founder Andrew Thompson emphasized that the new digital booking option is not designed to take the place of those human interactions or automate away the personal touch. Instead, the company is simply hoping to capture bookings that might otherwise be lost across time zones. 

That modernized front end doesn’t change the company’s commitment to its clients. Horizon still avoids same-day turnarounds, ensuring every boat gets the time it needs between guests, but still offering any day to any day charters- giving clients flexibility on travel and avoiding same day fleet turnaround bedlam. They also remain dedicated to keeping the one-on-one briefings and walk-throughs that have helped them maintain a loyal base of charterers.

New Boats and Broader Choices

This year’s fleet expansion reflects Horizon’s eye for yachts that can flex between markets. In November, a Jeanneau 55 will join the BVI fleet, becoming the largest bareboat-available monohull in the region. The boat is expected to be used both bareboat and skippered, aimed at sailors who want something closer to the kind of yacht they might own—or aspire to.

Though it’s officially a bareboat offering, this particular Jeanneau leans into comfort. It’s arriving with solar installed, a suite of water toys and extra onboard amenities.

Also joining the fleet in the BVI this winter are two large catamarans for the luxury crewed market—a Lagoon 55 and a Fountaine Pajot 67 For the bareboat segment, a Fountaine Pajot 44 will be added to the lineup as a three-cabin version, designed for groups that want more space without going full skippered. Overall the fleet remains equally split between catamarans and monohulls- a rare profile in the BVI these days.

These additions broaden Horizon’s footprint across price points and sailing styles, offering new size categories while maintaining their signature focus on boat quality, maintenance  and customer service.

Reintroducing St. Vincent

While the BVI remains Horizon’s flagship base, the company continues to push for greater awareness of its St. Vincent & the Grenadines location.

“The sailing is different there. Unlike the BVI’s compact cruising grounds, SVG offers longer reaches and more open-water passages, with fewer charter boats and more private yachts. For sailors looking for a slightly more challenging cruise, it’s a welcome change of pace”.

The payoff for this more advanced sailing is a less-trafficked location with a distinctly local feel. Guests are quickly welcomed—and not in the curated, cruise-ship sense. It’s part of what keeps people coming back.

“It’s not a tourist act,” Thompson noted of the local hospitality. “ It is the genuine island vibe”.

Thompson is also keen  to dispel any lingering concerns about past storm damage. The islands have rebounded from Hurricane Beryl, which made landfall as a Category 4 storm last summer.

“The region is ready,” Thompson said. “And the islands want to welcome the sailors.”

For many charterers, the appeal of SVG goes beyond the water. Fresh-caught fish, locally grown produce and small, family-run restaurants offer a dining experience that’s as memorable as the sailing itself.

Chartering Reimagined

In addition to new boats and tech-forward sites, Horizon is rethinking what a charter vacation can look like. The company is launching new experience-based itineraries that build in hiking, diving, watersports and dining. The packages are designed to expand a sailor’s trip without complicating it.

In the BVI, a new stay-and-sail partnership with Scrub Island makes it easier than ever to build hybrid itineraries that combine time ashore with time afloat. In St. Vincent, Horizon is encouraging guests to incorporate onshore hikes and inland excursions into their sailing plans.

The idea behind the itineraries is to ease each guest’s planning burden while opening up new ways to experience the islands. Travelers can still customize their routes, but they’re no longer starting from a blank slate. These themed itineraries provide a curated foundation that can either be built on or followed exactly.

Behind the scenes, a more responsive sales process aims to make trip planning feel more personal. With a new charter sales manager onboard, Horizon is offering more tailored inquiry responses and custom itineraries based on guest preferences, sailing experience and desired destinations.

Staying Rooted While Growing Outward

Even as the brand modernizes, Horizon remains firmly Caribbean-centric by choice. That doesn’t mean clients are locked into one region, however. The company is increasingly acting as a broker for partner fleets in destinations like Greece, particularly in the Northern Ionian, giving longtime clients a way to explore new waters without starting from scratch with an unfamiliar provider.

For a charter company that’s built its reputation on repeat bookings, that flexibility matters. Some Horizon clients have chartered more than 20 times in the BVI alone. Offering new experiences without losing the service quality those clients have come to expect is the throughline in all of these updates.

From upgraded tech to expanded fleets and destination variety, Horizon is charting its next chapter with care. Click here to learn more about Horizon.

The post Charting Forward: Horizon expands with new tools and a broader view of the Caribbean. appeared first on Cruising World.

Planning a Caribbean cruise or bareboat vacation this fall? Cruising World’s Caribbean correspondent David H. Lyman shares expert advice on routes, island cruising, and marine photography.

If you’re heading south to the Caribbean this fall or planning a two-week bareboat vacation among the islands, don’t miss three insightful seminars by Cruising World’s Caribbean correspondent David H. Lyman at the Newport International Boat Show this September. Drawing on his extensive offshore sailing experience and numerous voyages through the Eastern Caribbean, David’s presentations will equip sailors with the knowledge and confidence to make the most of their island adventures.

On Thursday, September 11 at 12:30 pm, David will present Sailing Offshore to the Caribbean: boats, crews, route and rallies, weather, designations and staying safe. This session is perfect for sailors planning their fall passage and covers everything from route options to Gulf Stream navigation, weather windows, vessel types, and safety tips.

Later that day at 2:30 pm, he will host Cruising the Islands of the Eastern Caribbean from the Virgin Islands to Grenada, offering practical guidance on island hopping, anchoring, customs, provisioning, and local amenities. This seminar provides firsthand insights for those dreaming of or preparing to explore the Leeward and Windward Islands.

On Sunday, September 14 at 2:30 pm, join David for Photographing Your Adventures Afloat: cameras, lenses, GoPros, drones, and how to see the world as a photographer. This seminar blends storytelling and technical tips, teaching you how to capture your cruising journey with compelling images, whether using a smartphone or professional camera.

All seminars take place in Room B – Below Deck at the Hammetts. Whether you’re a seasoned cruiser or new to bluewater sailing, David’s presentations will inspire and inform your next voyage to the Caribbean.

Get more information at newportboatshow.com.

The post Sailing South? Don’t Miss David H. Lyman’s Newport Talks appeared first on Cruising World.