Travel Destinations

Chartering the Caribbean


An inside look at this popular boating style

Charter vacations have grown in popularity over the years. Like other industries, it took a hit during COVID but has since skyrocketed in sales. In fact, the global yacht charter market is expected to rise from $6.50 billion in 2019 to $10.82 billion in 2027, according to a 2022 report from international market research publisher, Fortune Business Insights.

From bachelorette parties and milestone celebrations to fishing trips and relaxing getaways, chartering is a convenient way to make vacations a breeze. Whether you want a crewed charter to enjoy boating without manning a boat, or a bareboat charter to rent and return, the recent industry boom has allowed companies to increase services and streamline easy bookings and processes.

Bahamas-The Moorings-UPTOPMEDIA-7
Bahamas, The Moorings by UPTOPMEDIA

“There is rising marine tourism, aquatic recreational activities, and preference to chartering than ownership of motor and luxury yachts due to increasing ownership costs associated with yachts in markets such as Europe and North America,”notes a report from Transparency Market Research. The charter industry’s revenue is also estimated to rise by boosting services such as cabin, skippered and crewed chartering.

“The yacht charter market is witnessing a growing trend of innovative interior design such as the use of exotic leather ... and upholstery in the yacht. Sailing and motor yachts are becoming increasingly equipped with modern woodwork, lighting, and furniture,” Transparency Market Research also reports.

Travel with the local expects on a crewed charter and let loose while enjoying watersports and activities you can’t experience while captaining a vessel, or move at your own speed with the feeling of freedom while bareboating. Your charter company will work with you to not only accommodate all travel needs, but to also plan your trip based on the best weather conditions, routes, local knowledge and anything you want to make of the journey.


While tracking trends in the boating world, Marinalife also noticed an uptick in interest for chartering a Caribbean vacation. To help understand what’s behind this shift, we conducted an exclusive membership survey and came up with interesting insights that we’d like to share with our readers.

We chose our top 12 Caribbean destinations most frequented by our readers and asked about their favorite locations, what they love about chartering, and what season is best. We also inquired about helpful tips from their experiences.

We found that the U.S. Virgin Islands was the top destination by 74% of the respondents. Coming in second is the Bahamas at 43%. And British Virgin Islands (BVI) remains as one of the favorite charter destinations.

When it comes to the best season for chartering, winter was voted number one by 56%, followed by spring (48%), then summer (35%), with fall coming in last at 26%. The Caribbean winter season is known for dry, sunny clear skies and mild temperatures — a perfect time for snowbirds to plan a charter escape.

BVIs The Moorings Charters
BVIs by The Moorings

When readers were asked about what they enjoy most about chartering, the most common answer was, “freedom.” Boater Jim DelVecchio notes his favorite part of the experience is the freedom of bareboating. He suggests to book early to snag the best boats available. Richard Fisher, who also notes “freedom” as his favorite benefit of bareboating, gave a few tips for chartering the British Virgin Islands: “Know what you are doing, study the geography (nautical charts), relax and enjoy. Winds in the BVI tend to be brisk to potential gale force, especially in the winter.” He adds, “Get a catamaran — the absolute best platform for enjoying the BVI!”

Another boater Westray Paisley strongly recommends planning ahead. His number one tip: “Book early and do your port of call research.” Paisley cruised the British Virgin Islands with a group of eight in 2015, starting in Road Town, located in the BVI capital of Tortola. He says his group quickly learned that for the smoothest experience, you must have a flexible plan and take your time to enjoy all the gorgeous ports.

“We bareboated the whole trip, and it was very easy, because you are never out of sight of land. We arrived by the ferry from St. Thomas where our booked 54 Leopard power cat was waiting for us from The Moorings charter company,” says Paisley.

“Bareboat is the best for us, since we are all longtime boaters and enjoy the challenge and flexibility to do what we want, when we want. While the 54 Leopard has four staterooms, having a captain would have made it very tight,” he adds.

Have you chartered in the Caribbean? If so, we want to hear about your experience. Share your stories at


The following charter companies (including their areas of operation) are among some of the region’s top-rated services:

Carefree Yacht Charters

Dream Yacht Charter
Antigua, Belize, BVI, Cuba, Grenada,
Guadeloupe, Martinique, St. Martin, USVI

Horizon Yacht Charters
Bahamas, BVI, St. Vincent & The Grenadines,

Antigua, Aruba, Barbados, BVI, Cayman
Islands, Costa Rica, Cuba, Dominica,
Grenada, St. Barts, St. Martin, St. Vincent &
The Grenadines, Turks & Caicos, USVI

MarineMax Vacations

Navigare Yachting
Bahamas, BVI USVI

Nicholson Yacht Charters & Services

Antigua, Bahamas, BVI, Cayman Islands,
Cuba, Grenada, St. Lucia, St. Maarten,
St. Vincent & The Grenadines, USVI

Ritzy Charters
Anguilla, Bahamas, Belize, BVI,
The Grenadines, St. Martin, St. Barts


Antigua, Bahamas, Belize, BVI, Grenada,
St. Lucia, St. Martin, Martinique

The Moorings
Antigua, BVI, Grenada, Martinique, St. Lucia,
St. Martin, St. Thomas

Waypoints Yacht ChartersBVI, USVI

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