Sailing Charters in the Caribbean and Bahamas

All the charter companies listed below have sailing bareboat charters. All offer provisioning options and lengthy lists of included boat gear and amenities. As noted, some also have crewed charters, sailing courses, powerboat charters, and other services.

It's often difficult to compare the prices of charter companies because of differences in the boats, add-on options, provisioning, special offers, and other specifics. Sometimes there are only subtle differences in the bareboat rates of the companies listed here. The rating system here is based on the typical cost of a one-week bareboat charter of a 36- to 39-foot monohull appropriate for four or a small family or a catamaran of about 38 feet. When shopping, look for special offers and add in all costs to reach a total cost you can compare across companies.

Price guide:
$ Less expensive
$$ Average
$$$ More expensive

Choosing a Charter Company

Choosing a bareboat or captained sailboat charter company can seem a bewildering experience—especially if it’s your first time. You have to choose among different sailing locations, models and sizes of boats, provisioning and boat equipment options, and add-on services such as the services of a captain, sailing instructor, and shoreside amenities. At first glance the various charter companies may seem similar, making choices difficult.

To begin deciding which company and boat is best for you, start with these considerations:

1. Choose a sailing area. Different locations offer varying features, as you’ll discover quickly with some essential online research. For example, the Abacos, Bahamas, offers a close-by, protected sailing area that’s not too crowded but that has fewer attractions on shore, cooler water in the winter, and less spectacular snorkeling. The US Virgins Islands or the British Virgin Islands, a favorite of many charterers, has many charter companies, spectacular snorkeling, and popular shoreside attractions, but anchorages are more crowded. Other Caribbean islands offer more exotic locations, different cultures, and smaller crowds but often involve more expensive travel costs and fewer amenities for some American tastes.

2. Consider the options. If you have enough experience to bareboat, you may be ready to go. Or you may want a captain for a day or two until you get used to the boat, a crew and chef if you don’t want to go it alone, or a sailing instructor or full sailing school if you’re just starting out.

3. Determine your boat needs. Too small and you and your family or friends may feel cramped, too large and you’re paying for more than you need and maybe more than what you’re used to sailing. Newer boats that are well-equipped and clean as a whistle naturally cost more than older models that have everything needed for a good sailing experience but not all the options.

4. Check out the websites of the charter companies that fit your choices for the above criteria. You can get a good feel for each company by what they emphasize. Luxury? Amenities on shore? A small, family-run approach? A large company offering every possible option you could want?

5. Finally, compare prices. You may find just want you want at the price you can afford, or you may have to adjust your expectations in the decisions above.

While considering these matters and making your plans, check out this list of 10 Don'ts for Sailing Vacations.

Following are a wide range of charter companies with bases in the Caribbean and the Bahamas, listed alphabetically.

• Smaller, family-run business
• Charter captains available

• Smaller company offering personal service
• Boat inventory includes some older models at bargain rates
• Offers ASA cruising courses
• Represents luxury crewed yachts of varying sizes throughout the Caribbean

• Offers free online bareboat charter sailing course
• Crewed sailboats and crewed power yachts (41 to 102 feet)
• Diving charters and captain-only charters

• Smaller, family-run business
• Crewed sailboats and crewed power yachts (58 to 100 feet)
• Offers hired captains, cooks, or ASA instructors

• Promises to beat all equivalent competitors’ prices
• Charter captains and chefs available
• Offers last-minute booking specials

• Crewed sailboats
• ASA cruising courses at some bases
• Offers last-minute booking specials
• British Virgin Island packages include resort and spa facilities

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