Charter a Dream Vacation

Let Caribbean Yacht Crews Take the Helm


THE SEA'S RHYTHMIC splash under the twin hulls of the 58-foot Leopard catamaran quieted the sounds of civilization from the nearby harbortown of Charlotte Amalie, on St. Thomas, in the U.S. Virgin Islands. Steve O'sullivan looked over at his wife and smiled. She was relaxed, tucked into the cushions in the yacht's comfy cockpit with a cold beverage in one hand and a book in the other.

Exuma, Bahamas - Caribbean Charter - Marinalife
Exuma, Bahamas | GrizzlyMedia with The Moorings

He glanced up next to the flybridge. The couple's 18-year-old son and 20-year-old daughter talked animatedly about plans to swim and snorkel in the U.S. and British Virgin Islands during the week ahead.

O'sullivan sat back, cushioned his hands behind his head and gazed at the soothing blue of the Caribbean Sea. Captain at the helm, he thought, check. Chef in the galley, check. His family's 37-foot NorthEast motor yacht docked safely at home in Massachusetts, check. This was just where he wanted himself and his family to be casting off on crewed charter in the Caribbean.

The term crewed yacht charter often conjures up mental images of movie stars and millionaires lounging on megayachts with attentive crew ready to pour from magnums of champagne. This is true partially. A crewed yacht charter is best defined as an all-inclusive vacation on a luxury yacht hired for private use, where the stateroom view changes daily, and everything is customized for the guests from the gourmet menu to the made-to-order itinerary.

However, and particularly in the Caribbean, you can choose from hundreds of smaller yet no less sumptuous yachts, with licensed captains and culinary school trained chefs. Weekly rates, for example, span from U.S. $13,000 to $24,000 for a 50- to 90-foot sailing yacht, from $18,000 to $44,000 for a 45- to 75-foot sailing catamaran, and $22,000 to $45,000 for a 60- to 112-foot motor yacht. Rates are all-inclusive, except for the airfare to the destination and a 15% to 20% crew gratuity. Thus, crewed yacht charters are not just for the rich and famous.

A big part of this reality is the everyday way crewed chartering started in the Caribbean. In the early 1950s, Commander V.E.B. Nicholson sailed the family's 72-foot schooner, Mollihawk, from Ireland and docked in Nelson's Dockyard in Antigua. Island visitors soon started asking him to take them for a sail. He agreed, with day trips turning into overnights to nearby islands and his two sons serving as crew.

Sea Esta Yacht Charters - Caribbean Chartering - Marinalife
Sea Esta Yacht Charters

Up north, the U.S. Virgin Islands in the 1950s had a reputation for quickie divorces, but required divorcees to stay in the territory for 14 days. Enterprising young men, many of whom had sailed their yachts south from the U.S. mainland or Europe in search of adventure, earned extra income by taking these bored ladies and their friends out cruising.

Next door in the BVI in the early 1960s, a Navy veteran and his wife bought six 35-foot Pearson sailboats, called their new business The Moorings, and offered the yachts for bareboat (without crew) and crewed charters. Today crewed chartering throughout the Caribbean has matured into a boutique industry with a fleet of customized yachts and trained crew each with their own characters to match guests' needs and wants.

Crewed yacht charters have become increasingly popular over the past five years, as customers seek to curate a unique experience that you can't get elsewhere, says Dan Lockyer, vice president of global tourism for Dream Yacht Charter, headquartered in Annapolis, MD. Customers tell us they are looking to create a vacation of a lifetime without the hassle and worry. During COVID-19, it is the perfect isolation getaway where you can easily socially distance from crowds and limit your time ashore.

Why Charter if You Own a Boat?

The biggest reason for chartering a crewed yacht is to experience a true vacation without the stress of orchestrating things yourself, says Kristi Marquart, who with husband Brad, is captain and chef aboard Sea Esta, the Leopard 58 the O'sullivans chartered. Consider the time, distance, and expense it would take to move a personal boat to the Caribbean and back from the continental United States. You could maximize your relaxation and vacation time by letting everything be done for you, from understanding safe local routes to docking and anchoring, to food preparation and cleaning. You could also use a crewed charter to gain familiarity with the Caribbean for planning a future trip with your personal boat.

Another plus, adds Ann McHorney, charter broker and chief executive officer of Select Yachts, in Fort Lauderdale, FL, We get charterers who want to experience specific makes and models and the amenities on board a particular yacht to see if they wish to buy one.

Dream Yacht Charter in Tobago Cays - Caribbean Chartering - Marinalife
Dream Yacht Charter in Tobago Cays

In terms of what type of yacht to charter, choices include sail and power, monohull and multihull. Smaller yachts in the 40-foot range are perfect for honeymooners or two couples as they accommodate two to four guests. Fifty- to 60-footers carry six to eight, ideal for families or couples. Yachts in the 80-foot range accommodate up to 12, perfect for two families or three-generation family trips. Mini-mega yachts are also available in the Caribbean, from 100- to 150-foot classic schooners to power yachts. Of course, it's always possible to charter yachts like Hollywood billionaire's David Geffen's 452-foot Rising Sun, which is usually based in the U.S. Virgin Islands during the winter. What to choose depends on personal preference.

Many of our guests love to sail, and to sail in a beautiful destination such as the Caribbean is often a lifelong dream, says Ian Pedersen, senior marketing manager for The Moorings and Sunsail, headquartered in Clearwater, FL. In this case, the question then shifts to 'do I want to sail a monohull or catamaran?' Most sailors have experience sailing monohulls, but fewer have experienced with a catamaran. I would liken sailing a monohull to driving a sports car, while a catamaran is more like a minivan. One sacrifices space and comfort in favor of speed and performance, while the other is all about comfort and space at the expense of performance. Power catamarans are relatively new to the market and open the world of chartering to people with boating experience but who may not know how to sail. This segment of the charter market is skyrocketing in popularity.

Crew = Catered To

The Moorings in St. Martin - Caribbean Charter - Marinalife
The Moorings in St. Martin | Geoffrey Ragatz

The benefit of the crewed part of a charter is an endlessly customizable experience. Guests can tailor the route, dining options, drinks menu and water toys, which are a big trend including paddle boards, wake boards to pull with the yacht's motor dinghy, and floats shaped like palm trees and flamingos. Some crews have drones and underwater cameras to record take-home memories.

The culinary aspect of crewed charters is a priority as guests are often discerning foodies. They expect gourmet dining that wouldn't be out of place in a five-star restaurant and enjoy the element of adventure sailing brings, waking in a different location every morning. Service is delivered to a high standard, and crews are also invaluable personal destination guides with in-depth local knowledge, says Dream Yacht's Lockyer.

Where to Go?

The U.S. and British Virgin Islands are the number one choice for a crewed yacht charter, with more than 60 islands in each territory to discover. Highlights include the pristine white sand beaches of the Virgin Islands National Park on the USVI's St. John, famous rum huts like Foxy's Tamarind Bar on the BVI of Jost Van Dyke, and the iconic boulders and sea-filled grottos of The Baths on Virgin Gorda. To the east, Puerto Rico's offshore islands of Vieques and Culebra offer quaint restaurants, perfect snorkeling and a friendly vibe.

The Leeward Islands like St. Maarten, St. Barth's, Antigua and St. Kitts and Nevis are wonderfully international, each with its unique culture to explore. There are beautiful beaches, great restaurants, and a taste of Europe and the Caribbean all rolled up into one trip, says Select Yachts' McHorney.

The Windward Islands in the Southern Caribbean, especially St. Vincent and the Grenadines and Grenada boast the same multi-island appeal as the U.S. and BVI, but destinations are a little farther apart with some blue water cruising in-between.

We get a lot of inquiries for charter guests who feel they have 'done' the BVIs and are looking for a new charter destination, says Lesley Dowden, reservations specialist at the Horizon Yacht Charters base at the Blue Lagoon Hotel and Marina in St. Vincent.

How to Choose The Right One for You

To find the right charter, contact a company that offers crewed yachts. Examples include The Moorings and Sunsail, Dream Yacht Charter and Horizon Yacht Charters. The U.S. and British Virgin Islands both have crewed yacht associations, (see and and good resources for cruising grounds.

Perhaps best of all: Reach out to an experienced charter broker who serves as valuable resources to guide clients through the process, familiar locations, yachts, crews and industry to help match the best yacht for their clients. (See Charter Yacht Broker's Association at

Top Caribbean Charter Companies

BVI Yacht Charters

British Virgin Islands

Carefree Yacht Charters

British Virgin Islands, U.S. Virgin Islands, The Bahamas and The Grenadines

The Catamaran Company

British Virgin Islands

Dream Yacht Charter

Panama, Belize, Cuba, U.S. Virgin Islands, St. Lucia, Puerto Rico, British Virgin Islands, St. Martin, Antigua, Guadeloupe, Martinique, St. Vincent/The Grenadines, Grenada and The Bahamas

MarineMax Vacations

The Bahamas, British Virgin Islands, St. Lucia and The Grenadines

The Moorings

Antigua, The Bahamas, Belize, British Virgin Islands, Grenada, Martinique, St. Lucia, St. Martin and St. Thomas

Navigare Yachting

British Virgin Islands and The Bahamas


Antigua, Belize, Grenada, St. Lucia, St. Martin, British Virgin Islands and The Bahamas

Virgin Charter Yachts

British Virgin Islands

Waypoints Yacht Charters

The Bahamas, British Virgin Islands, U.S. Virgin Islands and Belize

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