How to Pick the Right Boat for Island-Hopping Bliss

Whether you’re looking for a bluewater cruiser or a boat just for Caribbean cruising, the choice depends on your plans. Digishooter/stock.adobe.com

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.

Hugely popular today, catamarans allow you to anchor close to the beach, and sometimes even nose into the beach itself. ozerkina/stock.adobe.com

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.

On a value basis, a proven distance voyager and Caribbean liveaboard like the Tartan 42 is a great option. Courtesy BVI Yacht Sales

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.

Ted, in green, and the rest of the Rashetiloff family. Courtesy Ted Reshetiloff

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.

Multihulls with features like the Neel 43’s open-living layout are well-suited for couples or families with an eye on island-hopping. Jon Whittle

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.”

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