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Chartering a Sailboat in the Caribbean
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Chartering a Sailboat in the Caribbean

Chartering a Sailboat in the Caribbean

Last April, Chris Kotchick, a Scranton, Pa., oral surgeon, and his family spent a week on a chartered catamaran in the calm, clear waters off the British Virgin Islands. A crew of two — part of the deal — ran the show.

Until then, Dr. Kotchick said, the sum total of his nautical experience had been riding ferries. But his search for a vacation that would appeal to his wife, Bridget, a high school biology teacher, and their two teenage children led him to a 50-foot-long boat, which they used as a base for swimming, snorkeling, wake-boarding and scuba diving as they sailed from island to island. They slept onboard and mostly skipped onshore restaurants, wowed by the crew-cooked meals that could be shared with their daughter, who has celiac disease.

As to cost, the trip was, for them, an affordable splurge — just over $20,000. “It wasn’t that much more than the blowout Disney World vacation we took when the kids were younger,” said Dr. Kotchick, adding that two others had joined the family on that trip. “And it was a lot more fun.”

Though the image of yachting in the Caribbean skews more oligarch than average Joe, the Kotchicks are far closer to typical crewed yacht clients than the likes of Jeff Bezos aboard his schooner, which is more than 400 feet long and cost a reported $500 million. After a pandemic lull, more people of comfortable, but not necessarily extraordinary, means are booking these trips, and the trend is edging higher. According to an April 2023 report from Fortune Business Insights, the global charter yacht market — including both crewed and sail-it-yourself, or bareboat, charters — is expected to grow 5.5 percent by 2030, with yachts under 40 meters (about 131 feet) accounting for the largest share.

Because the cost includes a crew, passengers don’t need specialized maritime knowledge, which means the trips draw a variety of travelers.

“Some of our clients are more into active sports, and others prefer relaxing with a book or checking out onshore restaurants, bars and resorts,” said Carlos Andrade, a captain who, with his wife, first mate and chef, Maribel Ramirez, has run trips in the Caribbean and elsewhere for more than 30 years, most recently aboard their 44-foot catamaran, Alizé. “But all of them love the outdoors and simply being close to water.”

For Steve McCrea, a broker at the yacht charter agency Ed Hamilton & Co., the most common question from prospective clients is whether their kids will get bored on a boat. “I tell them that, yes, it’s a sailing vacation,” said Mr. McCrea, who has been booking crewed Caribbean trips for 26 years, “but, in fact, it’s more like a floating resort on the move, with loads of activities, sports gear and great beaches where you can spend the day.”

Jim Grant, a broker at Carefree Yacht Charters, said passengers do not need to meet any specific benchmark of health or physical fitness. “If you can comfortably navigate jet travel to get to the boat,” said Mr. Grant, “you’ll be fine on board.”

In the Caribbean, crewed catamaran sailboats with their double hulls far outpace power boats and single-hull sailboats as the vessel of choice. “They’re more stable on the water, which is great for people without a lot of sailing experience,” said Mr. Andrade, the yacht skipper. “And in terms of onboard space, they can’t be beat when you compare different kinds of boats of similar length.”

A boat’s size and age largely determine the cost of a charter, with price bumps occurring during the holidays. For a weeklong trip for six passengers aboard an older catamaran with three en-suite guest cabins and a crew of two in its own cabin, the per-person fee starts around $2,500 for a vessel under 50 feet. That gradually rises to $5,000 and up for a somewhat larger and newer boat and zooms ever higher as size and newness increase. A week aboard a two-year-old, 80-foot catamaran with four en-suite cabins and a crew of four, for example, can easily approach $20,000 per person. In the Caribbean, the charter fee is usually inclusive, meaning that meals, alcohol and fuel are folded into the cost. Only the customary 15 to 20 percent gratuity is extra.

Crewed charter trips can fill up fast. “For the best selection, you should think about booking at least six months in advance for popular times like spring break, Easter and Thanksgiving,” said Els Kraakman, a British Virgin Islands-based broker with Waypoints Yacht Charters. “For Christmas and New Years, it can be more like a year.”

Unless you’re chartering a megayacht with its own gym and sauna, amenities are fairly uniform. Even on moderately sized vessels, they usually include Wi-Fi, air-conditioning, music systems, swimming platforms, on-deck showers (in addition to those in cabin heads), motorized dinghies for water sports and transport to shore, and an arsenal of sporting equipment like kayaks, stand-up paddle boards, and gear for snorkeling and fishing.

Alfresco, onboard dining is a big selling point, with galleys on many boats staffed by cooks with professional experience.

“The meals were fabulous,” said Steve Tyler, a retired process safety engineer from Kansas City, Mo., who recalled an especially memorable chicken-coconut-cream curry served on the 51-foot catamaran in the British Virgin Islands that he chartered earlier this year with his wife, Laura, and their 19-year-old and 23-year-old daughters. “Our daughters are so busy with their own lives,” said Laura Tyler, a family law attorney. “It was wonderful for all of us to share three meals a day.”

Brokers arrange most crewed charter trips in the Caribbean, especially for first-time passengers, with the standard 15 percent broker’s fee being paid by the boat owner. Brokers can book virtually any yacht with a crew. The best of them, however, tend to work exclusively with charters run either by boat owners themselves or a team dedicated full-time to the boat — what some call true charters — as opposed to bareboat operations with a freelance captain and cook hired for a single trip.

Many websites appear to offer brokerage services, but actually function more as booking sites. “Real brokers talk with clients before booking to get a sense of who they are and what their expectations are for the trip,” said Mr. Grant. “Based on those conversations, they recommend boats and crews they actually know about from prior bookings, personal connections or visits to the annual charter yacht shows.” Many top brokers are members of professional associations like the Charter Yacht Brokers Association or the American Yacht Charter Association.

Matching crew to client is particularly important. In addition to running the boat and cooking meals, crew members act as hosts, concierges and de facto tour guides, and they can be in close quarters with clients, especially on smaller boats.

When you consider that there are roughly 7,000 islands in the Caribbean region, choosing one or several for a crewed charter might seem daunting. But the Caribbean’s charter fleet is concentrated in only a handful of locales with the right combination of good sailing and onshore services. Itineraries tend to be similar no matter how big your boat is. In fact, smaller vessels often have an advantage in being able to travel and overnight in shallower, close-in waters that are off-limits to mega yachts.

In the Bahamas, a popular destination that technically lies in the Atlantic Ocean, boats (including power yachts) make trips from Nassau into the Exumas, a chain of 300-plus low islands and cays with few inhabitants and miles of beaches. The U.S. Virgin Islands, with National Park Service sites and other onshore attractions, boasts a significant charter fleet. In the Leeward Islands, Antigua and St. Martin appeal to those looking for serious ocean sailing and, in the case of St. Martin, especially the French side, good food. South of normal hurricane routes, St. Vincent and the Grenadines, a group of 32 cays and small, agricultural islands, sees an influx of charter boats during what is peak hurricane season for many other Caribbean islands.

The top destination by far, however, is the British Virgin Islands, 50-plus diverse islands — some sparsely inhabited, others dotted with resorts and well-known watering holes — whose terrain ranges from green mountains to sugar-sand beaches.

On their separate trips, the Tylers and Kotchicks each hopped around islands like Tortola, Jost Van Dyke and Virgin Gorda, and made the longer sail to more remote Anegada, home to vibrant pink flamingos.

For the Tylers, the British Virgin Islands trip, which ran about $20,000, was likely a once-in-a-lifetime vacation. “It was expensive,” said Laura Tyler, “but definitely worth it in terms of the memories we created.”

The Kotchicks, however, aren’t ruling out another crewed charter. “I’d do it again in a heartbeat,” said Dr. Kotchick. “The only question is where.”

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