If you love the idea of a pocket daysailer that looks timeless yet sails like a thoroughbred, the 2011 Alerion Express 33 Gallup should be on your radar. Currently listed for $195,000 in Chebeague Island, Maine, our editors see her as a standout in the brokerage market, an ideal choice for anyone craving performance, comfort, and classic aesthetics.

The Alerion Express 33 blends a modern, sporty hull with the traditional beauty of a Herreshoff-inspired topsides design. Step aboard Gallup and you’ll immediately notice the spacious cockpit, complete with high backrests, pedestal steering, and twin electric winches that put all sail handling within easy reach of the helm. A powerful sail plan with a self-tacking jib keeps things simple for shorthanded sailing, while the responsive helm and stable underbody ensure an engaging, confidence-inspiring ride.

In 2019, Gallup underwent a significant suite of upgrades totaling over $110,000. Highlights include a new in-boom furling system (a rare and highly desirable feature), new mainsail, hull paint, dodger portlights, and electronics. Since then, she’s seen only light summer use and has been stored inside with heat protection each winter.

Below deck, the Alerion 33 surprises with thoughtful, efficient accommodations. A forward V-berth provides private quarters, while the main cabin offers twin settees and generous shelving. The galley includes an Origo alcohol stove, top-loading Isotherm fridge, stainless steel sink, and plenty of storage. The head compartment is well-appointed with a Raritan marine toilet and deck hatch for ventilation. The teak and holly cabin sole, solid teak doors, and formica bulkheads maintain that signature Alerion balance of classic style and functional elegance.

Construction-wise, the Alerion 33 is a high-quality composite design. The SCRIMP-infused fiberglass hull features end-grain balsa core and vinylester resin reinforcement, with stainless steel through-bolted chainplates, a fin keel with lead bulb, and a carbon double-spreader Hall Spars mast. Decks and cockpit boast varnished teak trim, full-length cockpit seats, and a removable cockpit table, ideal for daysailing and short cruising in style and comfort.

Powered by a 20-hp Yanmar diesel engine with saildrive, Gallup cruises at an easy 8 knots under sail, with a range of 115 miles under power. The boat comes fully equipped with a Fortress anchor, life jackets, winch handles, fenders, and more. Yes please! 

Specifications:

• LOA: 33’ | Beam: 9’3” | Draft: 5’0”
  
• Engine: Yanmar 3YM20C, 20 hp diesel
  
• Fuel: 18 gallons | Fresh Water: 11 gallons
  
• Cabins: 1 | Heads: 1
  
• Price: $195,000 | Location: Chebeague Island, ME
  

With its combination of classic aesthetics, modern sailing performance, and high-end upgrades, Gallup is a rare find in the brokerage market, a boat that delivers both style and substance in equal measure. For sailors seeking a daysailer-cruiser that turns heads at the dock and delights under sail, the 2011 Alerion 33 is a solid choice currently offered for sale with Wellington Yacht Partners. 

The post Used Boats We Love: 2011 Alerion Express 33 appeared first on Cruising World.

Current Yachts, a new entrant in the yacht brokerage world, has officially launched a platform aimed at transforming how yachts are bought and sold. The Annapolis-based firm introduces a patent-pending service model that replaces traditional 8-10% commissions with transparent flat-rate pricing, while maintaining professional brokerage standards.

Co-founded by marine industry veterans Amanda Haley of Fort Lauderdale, FL, and Maryline Bossar of Annapolis, MD, alongside technical co-founders Jeff Dorso and Sean Walsh, Current Yachts seeks to address long-standing frustrations among yacht sellers and buyers.

“The yacht industry has operated under the same outdated commission model for decades. It was about time we challenged it with a fresh take,” said Haley. “Not only are we offering professional brokerage services at a fraction of the cost, we’re elevating the standard of our profession by giving our clients the most clarity, itemizing our services and explaining the co-brokerage dynamic.”

A distinguishing feature of the Current Yachts approach is the dual-role team supporting each transaction. Every deal pairs a licensed yacht broker with a transaction manager to expedite sales, coordinate showings and surveys, and guide clients through settlement. “With our team approach, we expedite every step of the sale or purchase,” said Bossar. “The seamless communication tools we have built into our process vastly improve accountability to yacht sellers and streamline the entire transaction from listing to closing.”

The platform also includes online tools for listing intake, vessel valuation, payment processing, and soon, real-time analytics and feedback. Sellers retain control over co-brokerage commissions, creating a more efficient marketplace while potentially improving retained equity.

Current Yachts will make its public debut at the 2025 Annapolis Sailboat Show from October 9-12 at booth AB-22. The company will host a press conference Friday, October 10, from 10:30-11:00 AM. Visitors can explore the new brokerage model firsthand and participate in a daily treasure hunt supporting charitable initiatives.

Current Yachts represents a tech-driven alternative to traditional yacht brokerage, combining cost transparency, professional service, and modern platform tools designed for today’s buyers and sellers.

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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.

Few cruising yachts capture the spirit of rugged adventure and refined comfort like the American Tug 41. Launched in 2000, these semi-displacement trawler-style cruisers have earned a devoted following for their ability to handle some of the most challenging cruising grounds—from the winding waterways of the Pacific Northwest to the iconic Great Loop.

Seaglass, a 2006 model, designed by Lynn Senour and currently represented for sale by Wellington Yacht Partners, stands out even among this respected lineage. With a meticulous recent refit and upgrades totaling over $300,000, she embodies what happens when thoughtful owners commit to preserving and enhancing a boat’s performance, comfort, and reliability. Her 540-hp Cummins diesel engine powers a cruising speed of 9 knots with impressive fuel efficiency, yet can push her to nearly 16 knots when time or weather demand.

Belowdecks, the two-cabin, two-head layout offers spacious accommodations designed for long-term cruising. Natural light floods the salon and pilothouse through panoramic windows, while modern comforts like air conditioning, a full galley, and integrated entertainment systems create a welcoming refuge underway or at anchor.

Sophisticated electronics—including a comprehensive Garmin navigation suite with radar, thermal imaging, and autopilot—provide peace of mind, while thoughtful details like freshwater flush systems, bow and stern thrusters, and a joystick-controlled dinghy crane make daily handling and dockside maneuvers seamless.

With hull and deck constructed for durability and noise reduction, Seaglass is built for years of safe, comfortable exploration. Whether cruising inland rivers, coastal passages, or remote anchorages, the American Tug 41 remains a favorite for those who want a capable, no-compromise cruiser.

The American Tug 41 — Crafting Comfort and Capability

Launched in 2000 by Tomco Marine Group in Washington State, the American Tug 41 quickly became a standout among semi-displacement cruisers. Designed by Lynn Senour (best known for his work with Nordic Tugs), the AT41 blends the charm of a working tugboat with the comfort and systems of a well-equipped motoryacht.

Built tough for Pacific Northwest waters, the AT41 features solid fiberglass hulls below the waterline, integrated stringers and bulkheads, and a thoughtful layout that maximizes livability and visibility. Owners love the boat’s ability to cruise efficiently at 8–9 knots, but also appreciate the option to power up to the mid-teens when needed.

What makes the AT41 truly special is its versatility: it’s at home in tight canals, remote anchorages, and open water alike. Bridge clearance is low, access to mechanical spaces is excellent, and the layout fits couples or families equally well.

More than two decades after its launch, the American Tug 41 remains one of the most sought-after cruising tugs on the market—and boats like Seaglass show why, reminding us that cruising is as much about soul and stewardship as it is about speed or destination. They carry stories forward—of thoughtful care, innovation, and enduring style—helping inspire the next generation of cruisers to seek out vessels that are built to last and crafted for life aboard.

Keep an eye on this series for more “Used Boats We Love” — timeless long-range cruising boats (sail and power alike) that define cruising culture, craftsmanship, and the joy of exploration.

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Some yachts transcend the marketplace. They’re not just boats for sale; they are chapters in the story of American sailing craftsmanship and offshore adventure. The 2001 Hinckley Sou’wester 59CC Zanetia is one such vessel—an elegant synthesis of tradition, innovation, and timeless style that continues to inspire, no matter where she sails or who commands her.

Zanetia represents the pinnacle of the Sou’wester 59 line, the final and most advanced hull built by Hinckley Yacht Company. Designed by the esteemed naval architects McCurdy & Rhodes, she is a masterpiece of yacht design that marries classic lines and modern materials. Her Kevlar and carbon fiber composite hull—built with a patented vacuum bagging process—offers strength and lightness that were revolutionary at the time and remain impressive today.

Inside, her satin-finished cherry woodwork, teak-and-holly soles, and meticulous joinery are the hallmarks of Hinckley’s unwavering commitment to craftsmanship. With three private cabins, accommodations for eight, and a private aft owner’s suite with companionway access, Zanetia blends luxury and practicality for serious bluewater cruising.

Her keel-centerboard design offers the best of both worlds: shallow draft access to hidden anchorages and solid offshore performance with the board down. Electric winches, an electric headsail furler, and a powerful Yanmar diesel engine make her manageable for a small crew, while systems like Espar heating, reverse-cycle A/C, and a high-capacity watermaker ensure comfort across climates.

Zanetia carries a fascinating pedigree. Originally commissioned by an English lord and once a member of the Royal Yacht Squadron, she’s a boat with stories embedded in her varnished bulkheads. She’s featured in celebrated sailing books and remains a shining example of American yachtbuilding excellence.

For anyone passionate about cruising yachts that combine heritage, seaworthiness, and elegance, the Sou’wester 59 remains a beacon. Even if Zanetia is no longer on the market, her legacy endures as a benchmark of what bluewater cruising yachts can be.

Why the Hinckley Sou’wester 59 Still Captivates Sailors

Built between 1983 and 2001, the Sou’wester 59 line was Hinckley’s answer to the cruiser who demanded beauty, offshore capability, and meticulous craftsmanship. Only 16 hulls were built, making each one a semi-custom masterpiece.

The transition from traditional fiberglass to Kevlar and carbon composites during the final builds like Zanetia marked an evolution in durability and weight-saving that continues to influence yacht design today.

Hinckley’s attention to detail—from satin cherry interiors to the thoughtfully engineered deck layouts—ensures these yachts remain as functional as they are beautiful decades later.

Used boats like Zanetia remind us why sailing is as much about soul as it is about hull speed. They tell stories we carry forward, inspiring the next generation of cruisers to seek out the perfect balance of tradition, innovation, and enduring style.

Keep an eye on this series for more “Used Boats We Love” — timeless yachts that define cruising culture and craftsmanship.

The post Used Boats We Love: 2001 Hinckley Sou’wester 59CC <i>Zanetia</i> appeared first on Cruising World.

Some boats are simply vessels, but Matsya is something more—a whisper of history, a guardian of quiet waters, a keeper of wooden grace. She has carried me across Narragansett Bay with a steady hand and an easy motion, her Herreshoff lines cutting cleanly through time itself. On her mooring, she turns heads. Under sail, she turns moments into memories.

But even the most beloved boats deserve devotion, and Rhode Island summers are fleeting. My heart has drifted toward wingfoiling, and Matsya deserves a captain who will hoist her sails as often as the wind allows.

One of the last of her kind—a Herreshoff Marlin, not to be confused with her fiberglass namesake—she was lovingly rebuilt in the 1990s and remains in excellent condition. She is ready, as she always has been, to carry a new steward toward peace, adventure, and the simple joy of sailing.

If you’ve ever dreamed of owning a true classic, this is your chance. Matsya is waiting. For more information, CLICK HERE.

The post Ode to <i>Matsya</i>: Classic Sailboat Seeks a New Steward appeared first on Cruising World.

Cruising World’s Caribbean correspondent, David H. Lyman, was at the Newport Boat Show in September, where he organized and hosted a series of seminars. On Friday, the topic was “The Ideal Boat for Caribbean Cruising.” David invited two brokers and a cruising couple to discuss the boat shopping and buying process.

One of the speakers, Ted Reshetiloff, a broker at BVI Yacht Sales and general manager of B&G Marine Services at Nanny Cay on Tortola in the BVI, provided valuable insights into shopping for and purchasing a boat in the Caribbean. Below is a lightly edited transcription of Ted’s presentation.

“In 2012, my wife, Claudia, and I bought a Wauquiez Amphitrite 43 ketch that we named Demeter. We refitted the boat in New England, quit our jobs, sold everything, and set off cruising. We sailed throughout the Caribbean for about a year and a half, as far south as Trinidad and Grenada. We home-schooled our two kids as we sailed. When funds ran low, we had to decide whether to return to the States or find a way to make life work in the Caribbean. An opportunity in yacht management in the BVI came up, and we’ve been living in Tortola, mostly at Nanny Cay, for about 10 years now. Both kids are now in college—one at Massachusetts Maritime Academy, the other studying finance. In 2019, we began acquiring our new boat, Happiness, a Taswell 49. My wife and I now live aboard her in Nanny Cay.

As general manager of B&G Marine Services, I work with clients who want to keep their boats in the Caribbean when not cruising. We assist with logistics for bringing boats to the Caribbean, whether through delivery or shipping. While here, we manage maintenance, provisioning, and outfitting. We offer hurricane plans and look after boats during the summer. We also oversee large refits.

Scott Woodruff, the broker who spoke before me, mentioned the 80/20 rule. There’s no perfect boat that meets every need, so sometimes, you need more than one. Personally, besides Happiness, I also own a Diam 24 trimaran, which I keep in St. Martin for racing. I’m fortunate to enjoy both worlds.

When shopping for a boat in the Caribbean, there’s a lot to consider. Not only are there many sailboats on the market, but many are already here. Whether you’re looking for a bluewater cruiser or a boat just for Caribbean cruising, the choice depends on your plans. For example, a Beneteau 411 might not be ideal for an ocean crossing, but it’s perfect for cruising within the Caribbean, even for a 100-mile beat from Tortola to St. Martin. A Beneteau 473, on the other hand, would be better suited for longer trips.

The Caribbean offers great deals, too. Many people arrive intending to sail the world, but after their first bluewater passage, they realize offshore voyaging isn’t for them. As a result, boats already set up with solar panels, watermakers, and dinghy storage can often be found at affordable prices. It’s worth exploring these options.

When considering larger boats, Island Packets are a good choice. But I’m also a big fan of Hanse and the Amel 54, which are common in the BVI and throughout the Caribbean. We see many buyers acquiring boats from charter companies. New charter boats usually stay in the program for about five years before being transferred or sold. These boats offer great value but might lack some equipment. That’s where B&G comes in—we outfit them with lithium batteries, solar panels, watermakers, and more, while helping owners learn the systems they’ll need to maintain later in remote locations.

Alternatively, you can find a brokerage boat already equipped. From a financial standpoint, a pre-installed watermaker, solar panel, or lithium battery offers greater value. The previous owner has already paid for these, and since equipment depreciates quickly, the price you pay is often lower.

Catamarans are becoming increasingly popular in the Caribbean. It’s getting hard to find a spot for a monohull in the BVI anchorage. Personally, I prefer monohulls, but catamarans offer significant advantages, especially in terms of living space above the waterline and easy access to the water. They’re ideal for families and entertaining guests.

That said, some people find the offshore motion of a catamaran a bit unsettling, and it depends on the build. For example, there’s a big difference between an Outremer 45 and a Lagoon 450. Outremers are not mass-produced, and their high build quality makes them better suited for offshore work. Lagoon has its own advantages, with features that the Outremer doesn’t offer.

Another factor in choosing a catamaran is bridge deck height, which affects sailing performance. As Scott Woodruff said, the 80/20 rule applies here too. Most of the time, you’ll be at anchor, and catamarans are extremely comfortable for that.

We’re also starting to see more trimarans in the BVI, like the Neel, which are gaining popularity. They provide better performance, which is crucial in the Caribbean, where you’ll often be reaching between islands. A heavy bluewater cruiser might be more comfortable, but performance can be the difference between a one-day or two-day passage.

Whether you’re a first-time buyer or an experienced sailor, there are many factors to consider. The process of buying a boat in the Caribbean can be complicated, and I highly recommend working with a broker. There are two types: a seller’s broker, who represents the seller, and a buyer’s broker, who represents the buyer. While they’re often the same, a buyer’s broker will help you find the boat that’s right for you, not steer you toward one they’re selling. Broker fees are paid by the seller, so hiring one doesn’t cost you more, and their expertise is invaluable.

In the Caribbean, storage options are also a key consideration. Will you use your boat year-round, live aboard full-time, or sail back and forth? Are you planning to day sail, keeping the boat on the hard? These factors affect insurance, and it’s becoming harder to get insurance coverage in the Caribbean. This year alone, I’ve had five clients whose insurance companies now require mast removal when boats are hauled.

Managing boats during hurricanes like Irma was a game-changer, especially for insurance companies. A lot has changed since then, and it’s still evolving. Insurers want to know about your preparedness for hurricanes, whether you’ll be on the boat or relying on a management company. These are areas where B&G and other management companies can provide invaluable assistance.

This season, Hurricane Beryl struck the Grenadines in late June, causing significant damage, and many friends sailed down to help with recovery. Since then, the season has been quiet. Normally, we’d have had more hurricanes by September. The water temperature is unusually high—86 degrees in May where I live—and global warming may be influencing storm frequency and severity. It’s something we’ll need to monitor closely.

The world is changing, and I think you made a wise choice attending this show to keep learning. I’m about to turn 53 and have been sailing all my life, but I believe there’s always more to learn.”

The post How to Pick the Right Boat for Island-Hopping Bliss appeared first on Cruising World.

My Boat-Owning Background

I’ve been sailing for 50 years. I’ve owned and sailed four cruising boats and made dozens of offshore deliveries between Maine and the Caribbean. Each boat, each voyage has taught me something. Most of those ­lessons came from getting my hands dirty and venturing outside my comfort zone.

My first boat was Quinta, a 1947 34-foot Alden wooden sloop. I bought it in 1969 in Shelburne, Vermont, on Lake Champlain for $6,000. I fixed it up, and we motored down the lake, through the Champlain Canal, down the Hudson River, around Manhattan, out to Long Island Sound and Cape Cod, Massachusetts, then up to Maine. For the next 10 years, Quinta and I sailed up and down the New England coast with a compass, a radio direction finder and a sounder. I learned to anchor, managed to keep the Gray Marine gas engine running, and navigated by running aground, frequently. 

In 1979, friends joined Kate and me on a two-week bareboat charter in the US and British Virgin Islands. The boat, a Morgan Out Island, was a floating Winnebago, but it introduced us to a world I thought existed only in literature: the tropics. 

I was hooked. The islands of the Caribbean were everything I’d been ­dreaming about since I could read. There was warm, crystal-­clear water. Colorful fish. Coral reefs. Islands, each one different, with strange languages, dancing music and spicy food. The sun shone all day. The trade winds blew steadily from the same direction. At night, a warm breeze wrapped around my ­sunburned hide like a down comforter. 

I had to get back—on my own boat.

Fair-Thee-Well was another wooden sloop built in Maine in 1947. It was 42 feet and cost me $42,000. I was moving up. 

That boat and I sailed to the Caribbean in 1980, and back to Maine in ’81. Then back down the Intracoastal Waterway in 1984 to hop over to the Bahamas, and then back in ’85. 

By then, I’d had it with leaky wooden boats. That fall, I bought Afaran, a Lord Nelson 41 cutter. She was brand-new and cost me $125,000. With another $20,000, we outfitted her in Fort Lauderdale, Florida, and sailed to the Virgin Islands. 

I owned that boat for 10 years, sailing back and forth from Maine to the islands for the first five years. In 1987, Afaran and I rode out Hurricane Emily in Bermuda; then, in 1989, Hurricane Hugo in St. John, USVI. In 1995, we rode out Hurricane Luis in St. John, but a few weeks later, Afaran was lost in Hurricane Marilyn. I was not aboard to move the boat out of the way.

Yes, I still miss that boat. It showed me what it needed, taught me how to care, and gave me back twice as much. You might say that we had a relationship.

I’ve heard that you are supposed to own a boat whose length on deck is equal in feet to your age. In my case, that held true. After losing Afaran in 1995, I bought Searcher the following year. It was a 57-foot Bowman ketch built in 1976. It cost me less than $200,000, and with another $20,000, I ­outfitted it, and we sailed to the islands.

We made three round-trip voyages to the islands in the 14 years that I owned it—and I realized that I would not have been prepared to own and sail such a large, complex boat if I had not owned my three previous boats.

Boats are built of systems that need to be learned, maintained and occasionally replaced. Certainly, modern systems make the offshore voyage less stressful, but there’s still the weather, seas, currents and other ships to contend with, and the knowledge that you are out there, 300 miles from the nearest technical help. 

You are on your own, as you have perhaps never been. The only people farther away from help are the astronauts in space.    

Shopping Advice

The first piece of advice that I give people who are shopping for a boat is not to buy a boat.

Let me repeat that: Do not buy a boat. At least not yet. 

Sail on other people’s boats—as many different kinds as you can. Walk the docks and ask if anyone needs crew (assuming that you can properly cleat a line, tie a bowline, and pump the head). Pay for a ­bareboat-charter class or a DIY class. 

Before you even think about going ­offshore on your own boat, go with ­someone who has many voyages under their belt. This might cost you $4,000 to $6,000, but it’s a bargain as valuable research. For starters, it will teach you whether offshore sailing is your thing, and what to look for in a boat that fits you.

When you get to the actual buying, start small. I suggest a boat smaller than 30 feet. Within a year, you’ll learn a lot—and spend even more. There’s the cost of the boat, insurance, a mooring or slip to rent, the cost to haul and store your boat for the winter—it gets expensive. While doing all of that, you’ll also see if you actually use the boat enough to receive an adequate return on your investment. If not, charter a ­bareboat until your lifestyle justifies ownership. 

If your ultimate dream is to sail amid the islands of the Eastern Caribbean, or even around the world, then your preparations take on an even greater significance. The boat needs to be designed and built for long-distance offshore voyages. You’ll be spending weeks at sea, separated from any assistance, so you must be able to fix stuff that breaks, change fuel filters and bleed the injectors, rig an emergency rudder, patch a sail, and keep going. You will have acquired these skills working your way up while owning smaller boats.

Today’s offshore sailboats are technological marvels. If you are a gear person who loves fiddling with stuff, then these boats might not pose a problem. I’m still of the old school, and when navigating between Maine and the Caribbean, and through the islands, I use just Navionics on my smartphone. 

Top Considerations

I was walking the docks at the Newport International Boat Show this past year, looking for an offshore cruising boat. I found few. Only 20 percent of the boats at that show had masts. All the rest were ­power yachts. I did find two offshore ­sailboats that I liked.

Exodus, a Hylas 57, was impressive, but at $2 million, it’s a boat that only an experienced and wealthy owner could manage. A full-time captain might be required. 

The Island Packet 349 was a bit short at less than 40 feet, but Larry and Lin Pardey completed two circumnavigations aboard engineless boats under 30 feet. And the Packet has a full keel with an attached rudder to track well on long passages, along with smart bluewater features such as handrails along the entire coachroof. 

When I’m evaluating boats like these, I look for a number of key things. 

First is hull design: Sloop, cutter, ketch, yawl or schooner? They all qualify. A full or partial keel makes for better tracking over long distances. Narrow fin keels create less drag, meaning a faster hull and quicker turns around the buoys, but they require constant helm work to keep on course. Long keels and rudder skegs protect the prop and rudder. 

Waterline length: Longer is faster, but it’s also more costly to buy, operate and maintain. Many boats these days range from 38 to 48 feet, but more and more 50-plus-foot yachts are on the water. The difference in speed between a 45-footer at 6 knots and a 50-footer at 7 knots is 24 more miles in a day. On the 640-mile voyage from Newport to Bermuda, that 1-knot advantage gets you there half a day earlier. At 8 knots, Bermuda is whole day closer.

Catamarans: They have less wetted surface, are faster, have more living space, and have less heel, but my son, a yacht designer, tells me that once a pontoon leaves the water, stability begins to deteriorate drastically. “A cat is the most stable upside down,” he says. 

Tankage: If you’re going offshore to anywhere, you’ll need at least 100 gallons of fuel, enough to motor for 100 hours, four days, with another 30 gallons in jerry cans lashed to the deck as a backup. A few boats run out of fuel each year from inadequate tankage. Know your engine’s burn rate at different rpm.

Water: Two tanks are better than one because one could become foul. A watermaker? Sure, but that’s just another piece of expensive gear to buy and maintain. At a gallon per day of drinking water per person, a crew of four will need at least 60 gallons for a two-week delivery. Carry enough drinking water in extra jugs for emergencies.

Rig: A cutter rig is preferable to a sloop for going offshore. It’s easier to reduce sail and hove-to. A cutter or ketch affords more options in sail management. An inner forestay can carry a staysail or a smaller storm jib, but you’ll need running backs to support the mast. All headsails should be on furlers so that there is no need to go forward of the mast once at sea. Should you need to go forward, jacklines rigged from the cockpit exit point to the mast are better than those along the deck. Jacklines along the deck are fine for dragging you along in the water should you fall overboard, but jacklines rigged to the mast keep you from falling overboard in the first place. Look for handholds along the cabin top all the way and 30-inch-high lifelines—or, better yet, stainless-­steel rails. Those 24-inch ­stanchions can catch you at the back of the knees and flip you over the side.

Furling: How easy is it to reef and furl the main? Can it be done from the cockpit, or does someone need to go to the mast or climb onto the boom?

Anchoring: A windlass that’s hidden makes for a neat bow but is inconvenient. When it comes to setting and retrieving multiple anchors, the windlass needs to be on deck with a chain gypsy and a rope capstan—side by side, not stacked up—one above the other. You’ll need at least two anchor rollers on a well-built platform over the bow to accommodate a heavy working anchor on chain, as well as a second, ­lighter anchor on chain and rode. This lighter anchor can lower into the dinghy, run out, and set when there’s concern about dragging. A chain brake just forward of the windlass is a must, and I’d like to see a strong point on the foredeck—a Samson post—to secure snubbing lines, chain or a 1-inch mooring pendant. The deck cleats on many modern boats are barely adequate for dock lines. The windlass is not there to secure lines or chains. You’re apt to bend the shaft and render the thing useless. 

Convenience versus practicality: I recently delivered two modern cruisers. Compared with my previous boats, which were like camping in a tent, these were like motor homes. But with all the convenient push-buttons came a 50-page technical manual, or the need to bring along a technician. If you are buying a boat, ­remember the KISS principle: Keep It Simple, Stupid. Your new boat should be within your technical ability to keep it going.

Overall, if you’re up for the challenge and want to explore the world from the water, start small and learn as much as you can. Most of all, remember to enjoy the journey.

David H. Lyman is an author and award-­winning photojournalist who contributes regularly to Cruising World and other ­publications. Find him at dhlyman.com.

Useful Clicks for the Offshore Curious

Sailing Totem: Jamie and Behan Gifford are circumnavigators who provide practical ­guidance and exceptional coaching for safe, comfortable, happy cruising. sailingtotem.com

Lady K Sailing: Tim, a popular YouTuber, gives genuine unbiased advice about boats and boat ownership. ladyksailing.com

Sailing Avocet: Marissa and Chris Neely share their ­sailing adventures, from the technical aspects of cruising a classic sailboat to the challenges and triumphs of liveaboard life. svavocet.com

Yacht Hunters: Captain Q on YouTube provides a fresh, entertaining look at used boats. yachthunting.com

Offshore Passage Opportunities: OPO is an organized crew network that aims to create quality offshore passage opportunities for its members. sailopo.com

The post How to Buy a Boat: Smart Tips for Smooth Sailing appeared first on Cruising World.

The International Yacht Brokers Association (IYBA) has announced the launch of a comprehensive new database for yachts and boats of all sizes in a consumer-facing marketplace, Yachtr.com.

Powered by Yachtbroker.org, Yachtr gives brokers a new option to list their yachts, and potential buyers an intuitive platform to browse yachts and boats for sale worldwide. Yachtr is the result of several years of software development backed by industry associations and led by IYBA.

Once users visit the website, they can search verified listings that are for sale by category: motor yachts, cruisers, fishing boats or sailboats; by broker or by yacht manufacturer. The association’s From The Bridge blog contains a host of educational posts on topics such as: What is a Sea Trial and Why is it Important?, How to Hire the Right Captain for Your Yacht and Boat Insurance 101: Types of Coverage Every New Boat Owner Should Know. Users can also subscribe to have new articles sent directly to their email. Users interested in selling a vessel can be connected directly to professional brokers by searching either by name, city or zip code.

“Yachtr is taking control from private enterprise solutions and putting it back in the hands of the community,” said Paul Flannery, Chief Operating Officer, IYBA. “We have heard concerns from our members, and we believe that Yachtr addresses and solves the challenges that current listing sites present. We want to provide a platform that is accessible to all, and inherently fair in its approach to displaying listings. Yachtr is and always will be an industry resource, meant to better serve our community and the needs of the boat buying and selling public. We firmly believe that if the industry can be able to control their data that they will then be able to control their destiny and provide an enhanced consumer experience. Help us spread the word about a better way to buy and sell yachts where you’re always in control of your data.”

According to an IYBA spokesperson, Yachtr saw a 25 percent increase in listings during the first 30-day period. Currently, Yachtr offers over 14,000 listings from 285 yacht brokerages, with listings growing every day.

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Take a stroll down the docks at any boat show, and you’ll likely hear the classic quip: “The two happiest days in a sailor’s life are the day he buys the boat and the day he sells it.” While that might get a chuckle or two, for some of us, it’s more cringe than comedy. 

Boat ownership is like parenthood—exhilarating, but with challenges. Sure, the day you buy your boat feels magical, but the real hocus pocus happens when you launch it. I’ll always remember the day we took our 31-foot Hunter, Ragtime, off its mooring for the first time: engine purring like a contented cat, sails popping open and filling with life, wood creaking and rigging shifting as we heeled over on a close reach.

Our first shakedown cruise was up the Connecticut River to Hamburg Cove, where we anchored under the stars on a sheet of glass, my family and I sharing laughs and lobster bisque by the light of an oil lamp. It seems like yesterday. That, friends, is what boat ownership is all about. 

Now, selling a boat? That’s another story. When we finally waved goodbye to Ragtime more than 20 years later, it felt like parting with a family member. Every imperfection told a story—like the not-quite-white patch of cockpit nonslip where red wine was spilled one fuzzy evening on the hook in Fort Lauderdale, leading to a strict “no red wine aboard” policy. Ragtime was a floating scrapbook of memories. 

The infamous quip about the two happiest days probably came from someone who bought a fixer-upper and expected smooth sailing. Newsflash: Boats need TLC. A boat owner often has to channel their inner MacGyver to plug leaks, protect the gelcoat, keep the sails and rigging in good working order, and ensure that the engine runs smoother than a Steely Dan guitar solo.

Upkeep can be pricey if you’re not handy, and a boat’s initial charm can mask a lot of hidden issues. Excitement can quickly become frustration as maintenance costs soar. I get that. You probably do as well, which is why most of us learn to love the smell of marine grease in the morning and to find joy in every successful DIY repair. (If you know, you know.) 

If you’re already a boat owner, or are thinking of becoming one this fall boat-show season, the September 2024 issue of Cruising World has you covered—starting with marine industry veteran Ralph Naranjo’s guide to boat-show shopping, intended to help you navigate the often-overwhelming experience on the docks and ensure that you end up not just with a boat that you love, but also with one that meets your needs and dreams.

Also in the issue, off-grid adventurer Hilary Thomson’s “The Bricolage of Boating” delves into the art of DIY projects and how they bring sailors together as a vibrant cruising community. Cruising legend Jimmy Cornell, in “Chasing Perfection,” describes his five attempts to build the perfect cruising boat, giving us all a masterclass in perseverance and passion. And, with an active hurricane season upon us, sailing veteran David H. Lyman’s “Riders on the Storm” is a must-read firsthand account of surviving Hurricane Hugo that offers vital insights and a sobering reminder of the power of the sea.

While the adage about the happiest days might ring true for some people on the docks this season, it misses the heart of the matter. For die-hard sailors, the happiest days are the ones spent on the water.

My advice? The next time you hear that saying, just smile and keep your eyes on the horizon. Because for us boaters, the real happiness lies in the journey—not just the destination.

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