Somewhere, someone is about to fall in love. It might happen this fall, walking the docks at a boat show. Or online, browsing listings deep down a brokerage rabbit hole. Or aboard a friend’s boat, when the genoa pops, the water turns to mercury, and that little voice inside says, More please.

If that someone is you, I won’t talk you out of it. But I will say this: Boat ownership is not all smooth sailing and sunset anchorages. It’s a floating to-do list. It’s a crash course in troubleshooting, a master class in delayed gratification. It’s 90 percent chaos and 10 percent magic, and somehow, that math works. 

You’ll encounter new tools, new smells and new words. Most of them will be expensive. But somewhere along the way, you’ll also discover a part of yourself that thrives on challenge, adapts under pressure, and finds meaning in every hard-won nautical mile.

Full disclosure: Boats are demanding. They break. They leak. They never ask how your day is going before they throw something new at you. And we love them all the more for it.

When my family bought our first boat, I didn’t fully appreciate what we had signed up for. I just knew I wanted to go sailing. What I didn’t expect was how attached we, as a family, would get to all of it: the clatter of halyards in the yard, the smell of wet teak, the pride of knowing the boat inside and out because we’d rebuilt or rewired half of it ourselves. Our first cruise wasn’t flawless, but it was unforgettable, and that’s the ­currency of boat ownership.

Sure, as a boat owner, you might question your decision more than once. But then comes the moment—maybe on a perfect beam reach, or alone on the hook with ­coffee at sunrise—when the chaos subsides, the boat steadies, and you feel it: This is exactly where I’m supposed to be.

Boats also connect us to one another. How many dockside friendships have started with, “Hey, I noticed your solar panel setup,” or “Mind if I borrow your heat gun?” This is a community that rallies, whether to share knowledge, lend a hand, or swap stories over sundowners. Owning a boat brings you into that fold.

If you’re heading into boat-show season and hearing a little voice—Am I ready? Is it worth it?—the experts who contribute to Cruising World have your back. In our Hands-On Sailor department, Behan Gifford of Sailing Totem pulls back the curtain on marketing lingo like “turnkey” and “ready to cruise.” She also explains how to separate dream from delusion. On the other side of the coin, Avocet’s Marissa Neely unpacks what it ­really takes to prep a boat for sale, both emotionally and practically. She offers insights for sellers and ­future buyers alike. You’ll also find a pair of boat owners’ stories that remind us what this lifestyle is all about—seen through a purpose-­built ­passagemaker and an Atlantic crossing that tested not just the systems but ­also the soul of the journey, and from a solo sailor who wrestles with 3,000 miles of ocean and finds clarity on the other side. These stories matter because the boat-ownership experience isn’t just about the boat. It’s about what the boat makes possible. Boating is a platform for self-reliance, growth, escape and return, and everything in between. 

If you’re staring down your first haulout, chasing that elusive “perfect boat,” or trying to make sense of what “needs a little love” really means, we welcome you. No, you’re not crazy. You’re embarking on a journey that can be extraordinary.

In my experience, there’s always been that moment—after the bilge has been cleaned, the leaks hunted down and sealed, the errant halyard finally led fair—that you step back, wipe the grime from your hands, and catch a glimpse of your boat at rest. Maybe the sun is just beginning to arc low across the anchorage. Maybe you hear the soft clink of rigging in a light breeze. In that quiet instant, you remember why you fell in love with this life in the first place.

Is boat ownership worth it? 

You already know the answer. 

The post For the Love of the List (and the Life) appeared first on Cruising World.

There’s an old saying among sailors: “The two happiest days in a boat owner’s life are the day they buy their boat and the day they sell it.” While my husband, Chris, and I can confirm the unbridled joy of buying our beloved 1979 Cheoy Lee 41, Avocet, we’re not quite ready to test the second half of that theory. After years of pouring sweat, love and bottom paint into her, we’ve promised to keep her for the long haul.

That said, we’ve been crew on the emotional roller coaster of friends preparing to sell their boats. Trust me: It’s a ride with plenty of ups, downs and the occasional splash of regret.  

To demystify the process and help sailors prepare for what can feel like the nautical equivalent of sending your child off to college, I turned to two experts: yacht broker and sailor Josh Hannigan, as well as our pal and long-range ­cruiser Peter Metcalfe. They shared their wisdom, and a healthy dose of reality, on how to sell your boat while (mostly) ­keeping your sanity. 

The Right Timing

Let’s rip off the bandage: The right time is now. “If you’re ready to let go, just do it,” Hannigan says. “Boats aren’t like real estate. They’re not investments that appreciate. Every day your boat isn’t on the market is a day the perfect buyer isn’t seeing it.”  

Hannigan is more than a longtime yacht broker. He’s ­also a captain involved with yacht surveying, sailing ­instruction, and providing specialized services for ­watermaker systems and custom sails. He offers insights as an active sailor, instructor and liveaboard boat owner. He’s also an associate surveyor with the Society of Accredited Marine Surveyors and an instructor with NauticEd, making him a trusted adviser on boat ownership, maintenance and sales. 

For Hannigan, boats are less like houses and more like relationships: There’s someone out there who will love your boat just as much as you do. But timing, he says, is everything: “The right buyer might be waiting for a promotion, selling their property or finally retiring. If your boat is out there when they’re looking—and it’s the best option—it’s game on.” 

The trick, as with most relationships, is patience. Boats can take time to sell, and the seasons of the sailing world ­often ­dictate when interest peaks. But Hannigan says a well-prepared boat can sell at any time of year, provided it’s priced competitively and ­presented at its best.  

First Impressions

If you’re picturing buyers strolling onto your boat and falling in love at first sight, you’d better make sure it’s worth swooning over. 

“Think of it like staging a home,” says Metcalfe, who is in the process of selling his boat, the 38-foot Hans Christian Kessel, after completing a singlehanded voyage across the Pacific. “A clean, fresh-­smelling boat with shiny brightwork makes it easy for buyers to imagine themselves living their dream on board.”  

To prepare Kessel, Metcalfe embarked on a top-to-bottom makeover. “I revarnished the cabin sole, repainted the ­interior, refinished the teak, and even spruced up the deck paint. It was a labor of love—and a little heartbreak—but it made all the difference.”  

Hannigan agrees, but with a sharper edge: “Every scratch, chip and stain is a negotiation chip that you don’t want to hand over. Fix it now, or be prepared to lose money later.” 

His advice? Paint the bilge, tighten the hose clamps, and make the engine shine like you’re prepping it for a yacht show. “Every small detail adds up to one big impression: This boat is cared for,” he says. “Buyers can sniff out neglect faster than you can say ‘osmosis blister.’”  

Keep It Functional 

Boats are also like pets: They don’t do well sitting idle. Hannigan says systems left untouched for months will almost certainly revolt when you need them most. “Flush the heads, check the furlers, and make sure your wind instruments actually display wind,” he says. “Buyers will forgive quirks, but they won’t forgive neglect.”  

Metcalfe adds that honesty goes a long way: “If you can’t fix every issue, be upfront about it. Disclosing known problems shows you know your boat and aren’t trying to pull a fast one. Buyers appreciate ­transparency, and it builds trust.”  

I remember when we were buying Avocet. She wasn’t neglected, but she was ­definitely left untouched for months because the seller was in poor health. Luckily, we had a survey to support our concerns and could whittle the price down to a number that reflected the state she was in. 

The Right Price

Hannigan’s pricing philosophy is refreshingly straightforward: Price your boat fairly based on its condition and market comps. 

“Set a no-nonsense price that reflects a boat in good working order,” he says. “If everything works, buyers will pay for their preferences rather than penalizing you for deferred maintenance.”  

The Broker 

Selling privately can save you brokerage fees, but the process is not for everyone. Hannigan recommends asking, “Do I have the time, patience and knowledge to handle this myself?” 

A broker can take care of marketing, showings and paperwork, making the process smoother—especially if you’re emotionally attached to your boat. (And let’s face it, who isn’t?)

When choosing a broker, Metcalfe suggests going with your gut. Ask yourself: Would I buy a boat from this person? “If the answer is no, keep looking,” he says. “A good broker should be approachable, knowledgeable and genuinely interested in finding the right buyer for your boat, not just making a quick sale.” 

Patience Is a Virtue 

Selling a boat takes time. Hannigan likens it to getting out of a gang: “It’s not going to be easy, and it’s not going to be quick.”  

When it came to buying a boat, Chris and I took a whole year and put in two offers on two boats before Avocet fell into our laps. It took time, heartbreak and research to find the right boat. I can only imagine how Avocet’s sellers felt with the boat sitting on their hands for twice that amount of time. 

Budget for the time it takes to sell your boat and for the expenses involved in keeping it in show-ready condition. Whether it’s in a slip or dry storage, a well-maintained boat is far more likely to attract buyers than one that looks like it’s been left to fend for itself.  

Moving On

For Metcalfe, selling Kessel is bittersweet. “This boat carried me through some of my toughest times, but life has seasons. It’s time for me to move on.”

He expects tears when he hands over the keys, but also joy, knowing that the boat he loved is ready for its next adventure. We can’t wait to buddy-­boat with him again someday. We are confident he will be on the buyer’s side of thingssoon.

What he’s going through right now, though, is what so many sailors endure. It’s more than a transaction. It’s a rite of passage. Whether your boat has been a faithful partner, a dream realized or a character-­building challenge, preparing it for sale is your chance to honor its story while helping a new owner begin theirs.  

So, give it your best. Varnish the teak, clean the bilge, and light a candle in the galley for good measure. And when the right buyer comes along, hand over the keys with a smile, a handshake and maybe a little tear. 

After all, it’s not just a boat—it’s a piece of your life, setting sail for a new horizon.

The post How to Sell Your Sailboat: Pricing, Staging and Letting Go appeared first on Cruising World.

Gusting winds drive clouds of spray right across the bay. Deluges of rain blast across the long jetty that leads past the workshop and out to Sahula’sberth. I watch through my office window as the boatsurges against its mooring lines. Tropical Storm Tam has moved south to cover our part of New Zealand and is now officially a cyclone, one that is forecast to linger for another two or three days.

I am making little progress on the article I am trying to write. Yes, the window-shaking gusts of wind are a distraction. But the real culprit? A sheet of paper titled “Sahula’s Work List.”It lies right next to my computer.

It has been 16 months since we last made an ocean passage, south from a season in New Caledonia to my home base in New Zealand. Earlier this year, we decided to set sail and cross the Tasman Sea. Our goal: a leisurely meander through the islands and waterways of Australia’s Great Barrier Reef. Now we are just five weeks away from our planned departure, and Sahula’s work list still has 27 items on it. Most of them require relatively calm weather.

Yesterday, I printed out a ­copy and showed it to my partner, David. “Here’s what I need to get done before we set sail,” I told him.

“Need to or want to?” he queried.

His words echo through my mind as I try to work on an article about one of the yachts that my husband, Larry, and I delivered to finance our early cruising days. 

Back then, much of the cruising fleet was made up of smaller boats sailed by cruisers who looked for ways to earn as they wandered. Thus, there was a lot of competition for ­delivery jobs. When the owner of a big US-flagged ketch put the word out in Mallorca, Spain, that he needed someone to sail his boat back to New Orleans, a half-dozen cruisers wanted the job. The owner asked for a fixed price quote, one that would include the time and ­expenses of getting the boat seaworthy enough to set sail ­after ­having been sitting unused and neglected for two years. 

We really wanted the job. Our cruising kitty was getting low, and we welcomed the chance for an affordable visit to friends and family back home. We worked hard to come up with a competitive bid. We did a careful survey of the boat. The potential work list kept expanding: Haul the boat to remove a 2-inch mat of barnacles and growth, renew the upper shrouds that had broken strands just above the lower swages, repair two of the three bilge pumps, create a temporary whisker pole (the original had been lost in a blow). There was almost a whole page filled with faulty electrical items. The engine needed attention. By the time we sat down to work out our quote, the list was three pages long.

“OK, let’s be logical,” Larry said.  “We need to ensure that the boat stays afloat, the water stays out of the boat, the mast stays up, the sails go up and down, the rudder works, the stove works, and we can get fresh water out of the water tanks. Everything else is either a convenience or a luxury.” 

Then Larry began circling the items that fell into his “essential” category. With his cutback list, we figured it would take us about 15 days to get the boat underway, and 65 days to make the passage. The results: Our quote won. We got the boat to its owner within the time frame he’d requested. We had to do some jury-rigging along the way. We did put up with some inconveniences. But a few months later, we returned to where Seraffyn lay waiting near Mallorca, with enough “freedom chips” to cruise onward for another year.

I often think of that delivery trip when I meet people who have had their cruising dreams delayed or missed weather windows or even abandoned their plans because of “the work list.” That is why, when Larry and I presented seminars called “Priorities for Successful Cruising,” we would end the day by saying: “Two weeks before your planned departure, sit down and write out a complete work list. Add every job you think you should do. Then, go out on deck and let the wind blow the list away.  Rush below and write down the first six things you remember. Those are probably the most important ones. Get them done and go.”

That is the reality of caring for a boat, which is both your home and your adventure machine. There will always be things that could be done to make the boat easier to use or prettier. Things that might make life afloat “better.” 

The truth is, during all my voyaging life—which has ­included 100 or more ocean passages, included sailing with Larry on two different boats, ­doing delivery trips and, more recently, sailing with my current partner, David, on Sahula—there was only one time when every item was crossed off the predeparture work list. That was only when I agreed to sail with Larry on board 29-foot, engine-free Taleisin from the Atlantic to the Pacific around Cape Horn. The one condition I had: Everything had to be checked off the list when we made our attempt.

This was important to me for several reasons. It was highly likely we would face extreme weather. We might have to stay at sea for up to a month at a time. Our gear, our stamina would be severely tested. Crossing the very last item off the list just before we left Mar del Plata in Argentina and headed for The Horn helped ease the last concerns I had. (That last item? Put two changes of clothes plus a clean towel in vacuum-packed bags for emergencies.)

But the voyage I am now contemplating is not a bash around a great southern cape. It is the sixth time I will be sailing across the 1,300-mile width of the Tasman Sea. Even with unfavorable winds, it is unlikely we will be at sea for more than 10 or 12 days. With these thoughts in mind, I ­become determined to get something useful done despite the stormy weather.

I pull up my electronic copy of the Sahula work list. I put a check mark next to the items I know are essential to having a safer voyage: Add nonslip and paint the deck; sort the port vang line block; set up and test the Iridium Go for at-sea weather forecasts. 

An “M” (for “maybe”) goes next to a few other items that I really would like to get done if possible: Put trim over the new wiring in the loo, paint the compass, strip and varnish the companionway surrounds. 

I reluctantly put an “X” next to items that I realize might never get off the work list: Make a cover for the panel next to the companionway; add trim at the far end of galley. The list ends up with only seven check-marked must-do items and five marked “M.”  

As I am obviously not in the mood to write, I decide to brave the wind and rain, and head down toward the jetty. Though the wild weather precludes working on any of the check-marked jobs, there are two on the “M” list that I can do in the workshop.

As I begin cutting the first piece of foam which will ensure that my wineglasses and porcelain teacups will survive even the roughest sea, I think of David’s words. 

He was right. I was letting myself feel trapped by a work list cluttered with want-to’s.  Cutting back to the need-to’s set me free. 

After cruising more than 240,000 miles, US Sailing Hall of Fame inductee Lin Pardey is headed to sea again. Her latest book, Passages: Cape Horn and Beyond, encourages folks to go simple, go small, and go now.

The post Boat Work Lists Made Simple: Lessons from Lin Pardey appeared first on Cruising World.

For professional operators managing multiple boats, keeping tasks organized across teams is an ongoing challenge. Sailsense has introduced a new Team Tasks module to its mobile app, designed to bring more clarity and control to day-to-day fleet management.

The module offers a unified task list with smart filters, visual tags, and real-time updates, making it easier for teams to stay aligned and act quickly. Users can sort by status, assignee, boat, or priority, and track progress on everything from simple onboard checks to complex maintenance jobs.

Task creation has been redesigned for speed and simplicity. According to Sailsense, new defaults and streamlined inputs allow operators to add a clear description, assign responsibility, and set priority or due dates in seconds. Supporting documents, photos, or videos can be attached directly to each task, reducing back-and-forth and improving accuracy.

Communication has also been upgraded. The app now displays ticket history as a conversation thread, keeping all updates, messages, and shared files in one place. Push notifications ensure team members stay informed as work progresses.

The Team Tasks module is part of a broader Sailsense platform that includes automated SmartCare maintenance scheduling, performance dashboards, partner Points of Interest, BoatGuard security, and live boat data monitoring.

For Sailsense users, the update brings a more efficient way to coordinate operations and ensure no detail is overlooked. The new module is available now through the App Store and Google Play.

The post Boost Fleet Efficiency: Sailsense’s New Team Tasks Module appeared first on Cruising World.

Here’s a hopeful cruiser sentiment: “I don’t want a project boat; I want one that’s ready to go.” 

It’s a fair wish. Who wouldn’t want to skip the difficult refit and head off over the horizon? But a truly turnkey used cruising boat is more myth than reality. 

We’ve seen dreamers who buy budget-­friendly project boats get overwhelmed with the unexpected effort or cost and ­never leave the dock. Similarly doomed are the Pollyannas who buy that “ready to go” boat, only to borrow from their cruising kitty to correct myriad problems.

These are not cautionary tales. They’re more typical than not. Buying a cruising boat can be one of the biggest purchases in a lifetime, but unlike buying a house or a car, the search can be slower, messier and more emotional. Getting it wrong can cost thousands of dollars and multiple cruising seasons. 

Let’s talk about how to get this purchase right.

The Right Boat

Spoiler: There is no “best” boat for cruising. There isn’t even a “correct” set of features. It’s easy to get trapped by dogma, and much conventional wisdom is dated when it comes to what makes a bluewater boat. Just ask an AI bot, which feeds on outdated content and parrots a misleading response. Eventually, it will learn that a full or modified keel and heavy displacement hulls are not essential features for an offshore cruising vessel. 

Retaining old-school biases limits the inventory of candidate boats. Modern build techniques and design innovations give better sailing performance, more living and cockpit space, and an easier path to insurance. Helping people release biases around legacy bluewater design is a theme that we visit repeatedly in our coaching service.

What’s real is the boat that’s right for a particular buyer. To find that sweet spot of features, real feel and budget, start by envisioning cruising goals. Is the plan coastal or regional, such as the Caribbean, the Mediterranean or Mexico? Or are you thinking about crossing oceans and doing some multiregional cruising? Safety offshore has more to do with the sailor’s choices while cruising than with the make of boat.

Bob and Kim Stephens, currently cruising in the South Pacific aboard their Stevens 47, Meraviglia, say there are often mismatches between boats and sailors. They underscore that not all buyers are created equal: A buyer who knows boats, has owned boats, and has experience with boats is a significantly different buyer than one who is new to boating. Knowing yourself, including your skillset and risk tolerance, is as important as knowing your boat in determining the outcome.

The All-In Budget

To work out whether a boat fits in your budget, start with a purchase figure, then add a general rule to estimate the additional refit budget. 

Oh, wait—there is no general rule for refit cost. Every boat is different, and oversimplification will gloss over the likely budget necessary to make a cruising boat safe, reliable and comfortable. 

Instead, consider the total cost to purchase and equip a boat for your intentions. We call this the all-in budget: the total investment needed to purchase andprepare the boat for use. It includes purchasing costs beyond the negotiated price, such as survey and haulout, along with transaction fees, taxes, maybe delivery to another location, and the first year’s insurance. 

The refit is fixing known and surprise faults, adding missing gear, and replacing unsuitable or aged-out gear. Costs can add up, and new cruisers can hemorrhage money to reach departure day. Before committing to any boat, thoroughly assess its condition and gear to estimate refit costs. We use a spreadsheet template with fields for available budget, all purchase costs, and refit cost estimates broken down in categories, such as anchor gear, energy systems and rigging.

There is no “best” boat for cruising. It’s easy to get trapped by dogma, and much conventional wisdom is dated when it comes to what makes a bluewater boat.

If the all-in costs exceed the budget ceiling, then it’s time to negotiate a lower price, recalibrate to a different boat, or plant a money tree. 

Going through this process to vet a boat can be liberating or frustrating. Make sure the heartstrings tugging over the quality workmanship don’t overshadow the voice mumbling about the rigging age, lack of safety, and energy systems meant for being tied to a dock rather than off the grid.

Finding a Boat

Buyers often ask us where they should look. Online listings are a typical choice, and there are dozens of sites to browse. We track around 30 in our lists. A few sites list only brokered boats; others focus on private sales or specific regions, such as North America, Australia or Europe. 

A boat search doesn’t have to be limited to where you want to start cruising. Identical boats are likely to be priced differently depending on whether they’re in Florida, Maryland or Connecticut. It might make sense to cast a wider net and factor in the cost of relocation after purchase, especially if you’re not finding candidate boats in your local search area. 

Consider starting where the better-fit boat is, even if it’s not your originally planned location. Many buyers feel more comfortable purchasing a boat they can drive to. One common use case is the North American ­buyer who dreams of cruising the Caribbean. Purchasing to start on the East Coast feels easier and safer than buying a boat in Grenada. But to reach Grenada, the Florida sailor will go more than 1,000 nautical miles against prevailing conditions on the ­so-called Thorny Path. 

One Seattle-area couple we supported as coaches, Matt and Colette Rabdau, began their search focused on Leopard 44 catamarans. Colette made several trips to Florida, where, despite having watched video walk-throughs, she found gaps that drove up refit costs. They scaled back to smaller models with lower price points to allow more buffer in their funds. Ultimately, they acquired a Leopard 38.  

“We were glad that we ­shifted from a 44-foot boat to a 38-foot boat, as the money we did not spend was available to make other repairs, including replacing both fuel tanks, the front windows, all four cabin windows and portlights,” they told us via email. They also did some upgrades, adding Starlink, a higher-output alternator, a LiFePo4 bank and a watermaker.

Now two years into cruising the United States and Bahamas aboard Chinook, they say it was the right call to recalibrate. “If we had purchased the 44 [dream boat],” they write, “we would not have had the necessary funds for the upgrades and repairs that would likely have come up for other boats as well.”

Digging Into ­Listings

It’s tempting to treat a boat’s equipment list in binary fashion: Gear is either there or it isn’t. To avoid surprise expenses after a transaction, buyers should get a deeper understanding of each item’s condition. 

Many listings have checkbox lists instead of details. “Depth sounder” seems great, but what kind is it? How old? Similarly, an “autopilot” might be a bungee cord and a centered wheel. Maybe the listing says: “new batteries, 2019.” Well, are they lead acid or lithium? If they’re lead acid, they’re likely near their end of life—not exactly new or a selling point. 

Look carefully at photographs. Do the pictures show a pristinely painted engine? Overspray on parts not meant to be painted, such as formed hoses, suggests new paint on a not-new engine. Is this paint covering rust and corrosion from poor maintenance? And is the mainsail fully covered in those dockside images, or is the leech exposed and baking in the sun? How rusty is the anchor chain? 

Everything on a boat has a lifespan. As the buyer, you want to know where each item is on that timeline. This depends on the original quality of the item, how well it was installed, and how well it was maintained. 

Lifespan applies to nearly everything, not just the electronics. Our boat, the Stevens 47 Totem, is 43 years old. It’s been under our ownership since 2007, and we’re on the third standing rigging, the second engine, the third life raft, the third watermaker—not to mention bulkhead repairs, tank replacements and more.

Many listings have checkbox lists instead of details. “Depth sounder” seems great, but what kind is it? How old? Similarly, an “autopilot” might be a bungee cord and a centered wheel.

Buyers need detailed knowledge, or solid guidance, to assess each component’s stage of life. When a listing is thin, seek information from the seller or their representative. Sometimes, lifespan will be called out for them, such as when an insurance underwriter refuses to bind a policy until an aging rig is replaced. 

Digging into listings also means researching online history. One of our coaching clients went through social media posts by the seller of a boat they were considering. It turned out that the boat had been through a hurricane and sustained meaningful damage—so much so that the insurance company had totaled the boat. This information was not disclosed in the listing. They asked pointed questions of the broker. Screenshots supported their case after the seller deleted the content online. The state in which the boat was listed may not have required disclosure, but the code of ethics for professional yacht-­broker associations does—as does a basic moral compass.

Again, the goal is to understand the boat’s all-in cost. This cannot be done by applying a general figure or a percentage calculation. It is unique to every boat.

Working With a Broker

A good broker is a valuable asset during the purchase process. The broker provides market insight and access to the back-end data for some online listings to help inform your offer. 

The broker also acts as a buffer in negotiations with the seller and their broker. Owners are often emotionally attached to their boats. Explaining why your lower offer for their lovely vessel is fair can be difficult to do directly. After the survey and sea trial, brokers can again save you thousands by negotiating for adjustments to the accepted offer. 

Why doesn’t every buyer have a broker? It requires a reasonable budget to make the commission. This is often around the $150,000 mark. Not all brokers want to be a buyer’s representative. It’s not as lucrative. Their commission is paid by the seller. 

It’s also important to know what brokers don’tdo. Don’t expect them to scour listings to find that dream boat for you. That responsibility lies with the buyer, although a good broker will assist the process. And, of course, they will know what their own brokerage has available. 

Working with a buyer’s broker isn’t always a slam dunk. The Chinook crew’s Seattle-based broker did not advise them effectively about Florida taxation, an omission that cost them a considerable sum.

Resale Value

Avoid problems later by keeping resale in mind before you purchase. Consider demand: Is the make or model a name that people will type into search engines? Does the boat have an owners group? Resale value has geographic implications too. Designs revered in one region are undesirable in others.

An unusual boat—your “unicorn”—might be harder to sell later. The cost to carry a boat for sale, from dock fees to insurance, can get expensive. Boats often sit on the market for months. 

Also important: Refit expenditure does not add dollar-­for-dollar to resale value. A given make and model tends to have a market value. It will have some regional variation. It will sell faster or slower based on how well it is equipped or maintained. But $150,000 put into a $100,000 boat does not make it worth $250,000. 

Newer cruisers aboard their Beneteau, Paradise II, Chris and Shiela say that physically getting onto as many boats as they could was an invaluable part of the process. “Any boat,” Chris says. “Boats I could afford with change from the couch, and boats I couldn’t afford even if I sold both kidneys. Shiela suspected that she would not have been happy with a linear galley, and I knew I wouldn’t be happy with anything in the way from the forward cabin to the companionway stairs.” 

Those preferences knocked out lots of designs, but they helped to identify which boats they could afford and which of those retained market value. 

When To Pull the Trigger

Analysis paralysis is real. How do you break that cycle and commit to a boat? 

Internalize the idea that there is no ready-to-go boat, and then move ahead with due diligence and support. A mentor can help you ask the right questions, and can sometimes answer them too. 

Most important, make sure you buy with your head as much as your heart. A particular boat might pull your heartstrings, but do the math on the probable cost to make it ready for your dreams, and learn as much as possible about what you’re getting into. 

Then, the day you step aboard your magic carpet really will be one of the best days of your life.

The post Buyers Beware: Navigating the Boat Purchase Process 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.

When Sarah and I tell people we’re planning to sail around the world, we usually get one of two questions: “Where will you go?” and “What kind of boat are you doing it in?”

The first answer is simple: everywhere we can. High latitudes and tropical trade routes, quiet coves and remote anchorages, oceans to cross and people to meet.

The second question takes longer to answer—and the decision behind it took even longer to make.

We knew from the outset that this boat wouldn’t just be a mode of travel. It would be our home, our lifeline, and our entire support system for months or even years at a time. That made the search personal, and deeply mission-driven. The end result—our Boreal 56, Spindrift—is the product of months of discussion, dreaming, and refining what really mattered.

If you’re beginning your own search for a serious offshore cruising boat, we hope our experience helps frame the questions that matter most.

Start With the Mission

We began with a clear plan: to circumnavigate under sail, as safely and comfortably as possible. Our route would include everything from tropical trades to high-latitude routes with cold water, long passages, and unpredictable weather.

Our crew? Often just the two of us. Occasionally, our daughters Hannah and Samantha would join. Maybe, now and then, another couple. That meant two things had to be true: the boat had to be easily handled by two people, and it had to be rugged and forgiving in heavy weather.

We weren’t in a rush. Retired and finally free of the demands of career and commuting, we had time on our side. But that also meant we didn’t want to spend our retirement years tied to a dock, elbows deep in a refit or chasing system failures across foreign ports. We were looking for a boat that wouldn’t just go the distance—it had to arrive ready to go.

New vs. Used: The Time Equation

This led us to the first big fork in the road: old boat or new build?

There are plenty of excellent older boats out there, and we seriously considered going that route. But we also recognized that a “project boat” can quietly take over your life—and often carries invisible risks. In our case, the price of uncertainty outweighed the savings.

We didn’t want to be in a boatyard for the first year of retirement. We wanted to be at sea.

Material Matters: Why We Chose Aluminum

With the new-build route in mind, the next big choice was hull material. Fiberglass? Steel? Aluminum?

After plenty of research, conversation, and crawling around in boatyards, we decided on aluminum. For us, the pros—ruggedness, impact resistance, structural strength, repairability—outweighed the cons. We liked that aluminum deforms rather than cracks, and we trusted the long-term durability when built well.

The construction techniques used in our final choice were impressive: a thick keel plate, double-digit millimeter hull plating, and a monocoque structure that removed as many failure points as possible. Concerns about electrolysis are real, but manageable with good engineering and proper maintenance.

Hull Form and Handling: Comfort First

Comfort underway became a guiding value. Not comfort in the sense of plush cushions and granite countertops, but a kind motion—a boat that takes care of her crew in rough seas.

That ruled out multihulls for us. We gave them a fair look, even touring a Chris White Atlantic 55. But in the end, we preferred the motion and security of a monohull. One particular design caught our attention: the Boreal 56, a centerboarder with twin daggerboards—a rarity, but a configuration with huge upsides. It could go shallow, surf safely, and track well on long passages.

Weight distribution was also thoughtfully managed—fuel, water, chain, and batteries were centralized low in the hull. This created not just a more stable ride, but also increased internal volume where we needed it most: for storage, guest accommodations, and systems access.

The Rig: Safe and Simple

The rig design sealed the deal for us. We chose a Solent configuration with twin furling headsails and a main with deep reefing capability. Downwind, we carry a Blue Water Runner and a furling gennaker, all sized for short-handed control.

But what impressed us most was the attention to safety. The mainsheet is out of the cockpit entirely, mounted to the top of the doghouse—no traveler to fall into or trip over. Winches and sail controls are brought inboard where they can be handled safely from the cockpit. These details reflect real offshore experience. They’re not flashy—but they make a big difference in the moments that matter.

Finding the Right Builder

No boat is built in a vacuum, and in the end, the people mattered most.

After visiting many yards, we found one where the philosophy aligned with our own. The builder’s experience, integrity, and design evolution made a strong impression. The founder had clearly spent thousands of miles at sea and poured that experience into each detail.

What sealed the deal wasn’t just the specs or even the prototype—it was the team. The pride they took in their work. The thoughtfulness in their answers. The way every decision seemed tied back to the real-world question: “Would this make life safer, easier, or better for the crew?”

Final Thoughts

We know Spindrift isn’t the right boat for everyone. But for our goals, the Boreal 56 checked every box. And that’s the point.

There’s no single answer when it comes to boat selection. The “right” boat depends on your mission, your crew, your risk tolerance, and your sailing style. The only real mistake is not thinking hard enough about the decision.

Ask questions. Challenge assumptions. Visit builders. Talk to other cruisers. And most of all, know your priorities.

This was our process—and it led us to the boat of our dreams.

Offshore Cruising Boat Selection Checklist: A Practical Planning Guide for Cruisers Starting Their Search

Whether you’re dreaming of trade winds or tackling high latitudes, here are 10 questions to help guide your offshore boat search:

1. What’s your mission?
   Define your sailing goals—distance, locations, duration, and seasons.
   
2. Who’s your crew?
   Will you sail solo, as a couple, or with friends/family? This impacts layout, sail handling, and safety.
   
3. How important is comfort under way?
   Evaluate motion at sea, not just interior space. Try different hull types in different conditions.
   
4. Do you want a new or used boat?
   Consider time, budget, project appetite, and the hidden costs of a refit.
   
5. Which hull material fits your plans?
   Fiberglass, aluminum, and steel each have trade-offs in weight, repairability, and resilience.
   
6. How shallow do you want to go?
   A centerboard, lifting keel, or shoal-draft design could expand your cruising grounds.
   
7. Is your rig optimized for your sailing style?
   Look for a setup that’s safe and manageable by your smallest likely crew.
   
8. Can systems be maintained off-grid?
   Think about power generation, redundancy, and access to critical parts.
   
9. How is safety integrated into the design?
   Look beyond marketing—ask how design decisions reduce real-world risks.
   
10. Do you trust the builder?
    Visit yards, talk to past owners, and evaluate the yard’s philosophy and support.

About the authors: Tony and Sarah Mercurio grew up on the water in New Jersey and Rhode Island and now live on Long Beach Island, NJ. Lifelong sailors, they spent years chartering globally before commissioning their current world-cruising sailboat. In retirement, they’re pursuing a lifelong dream to circumnavigate aboard Spindrift, their Boreal 56. Follow their voyage at KrustyKrabAdventures.com.

The post One Couple’s Search for the Right Offshore Cruising Boat appeared first on Cruising World.

When it comes to living the cruising dream on a budget, few sailors are more qualified—or more colorful—than Cap’n Fatty Goodlander. In the second episode of Ahoy!, Cruising World’s signature podcast, we sit down with the legendary storyteller, three-time circumnavigator, and lifelong liveaboard to explore a life afloat that’s as unconventional as it is inspiring.

Born into a sailing family and raised aboard a 52-foot schooner, Goodlander took to the sea before he could even walk. Since then, he’s salvaged boats, built his own, weathered cyclones, and logged more offshore miles than most sailors will see in a lifetime—all while staying true to his frugal philosophy.

As Goodlander often emphasizes, cruising isn’t about spending money—it’s about making it memorable.

This episode dives deep into what that means. We hear tales of self-reliance and resilience, from refitting wrecks to riding out storms with nothing but grit, good seamanship, and a well-stocked sense of humor. Along the way, Goodlander shares the kind of hard-earned wisdom only a life offshore can teach, from embracing simplicity to navigating relationships in close quarters—especially with his longtime partner and first mate, Carolyn.

Though no longer a contributor to Cruising World, Goodlander’s voice remains one of the most iconic in the cruising community. He’s authored more than a dozen books and countless columns over the years, all infused with his trademark wit, candor, and deep love for the sailing life.

Whether you’re a salty liveaboard, a weekend sailor, or just harboring the dream of cutting the docklines someday, this episode is a reminder that adventure under sail doesn’t have to come with a luxury price tag.

Listen now on Spotify, Apple Podcasts, or wherever you get your podcasts.

The post PODCAST | The Art of Frugal Cruising appeared first on Cruising World.

As electric propulsion, solar panels, and eco-friendly antifouling paints gain traction in the marine industry, a new study confirms what many sailors and cruisers have suspected: sustainability is no longer a fringe concern—it’s a key factor for most buyers.

According to Unmuted Consumer Insights’ 2025 U.S. Boat Owners Sustainability Study, 68% of American boat owners say a brand’s commitment to sustainability plays a role in their purchase decisions. The study surveyed more than 750 owners of power and sailboats across the country, revealing a clear trend toward value-based buying behavior.

“Sustainability matters,” said Bridget Millar, president of Unmuted Consumer Insights. “Over two-thirds of boat shoppers now consider a brand’s environmental practices as part of their decision-making process—a trend that’s reshaping the future of recreational boating.”

Among the most intriguing findings: 54% of respondents said they would consider purchasing an electric boat if shopping today, reflecting growing openness to greener propulsion. However, the study notes that purchase intent doesn’t always equate to action, as concerns around range, infrastructure, and performance still linger.

Other data points showed a strong link between owner satisfaction and how often they use their boat—along with the length of the vessel—suggesting that boaters who are more engaged with life on the water may be more attuned to the environmental impact of their cruising lifestyle.

As sailing brands and builders increasingly market their sustainability credentials—from recyclable hull materials to hybrid drive systems—this report offers fresh insight into how eco-awareness is influencing consumer choices on the docks.To learn more, you can download the full summary report at unmutedci.com.

The post New Study Finds Majority of U.S. Boat Owners Prioritizing Sustainability 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. 

The post Confessions of a DIY Charter Skipper appeared first on Cruising World.