How to Charter a Yacht for the Ultimate Caribbean Boating Adventure

There are about seven thousand islands in the Caribbean, but most travelers only have time to visit one or two during their vacation. Typically, most people fly in and stay put or maybe they'll take a cruise, which only allows for quick visits at all the predetermined ports of call. It's understandable why so few people go island-hopping, since regional airlines are expensive, and ferry service between islands is often limited or nonexistent.

However, experienced boaters will tell you that the best way to see multiple islands in the Caribbean at your own pace is by chartering a private yacht. Invite some friends along with you and this pricey-sounding adventure could even be more affordable than you realize—or at least equal to what you'd pay for a high-end hotel room.

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Where to Go for the Best Caribbean Yacht Experience

Caribbean catamaran

Vera Kratochvil /  Public Domain

Yacht charters are available all across the Caribbean, and most islands have hidden beaches, beach bars, dive stops and sheltered anchorages you can plan your itinerary around.

Geography dictates that if you want to see more than one or two islands, you'll need to head to destinations that have multiple islands within an easy half-day (or less) sail from one another. In the Caribbean, that primarily means the Virgin Islands and the Grenadines, as well as St. Maarten, which reasonably is close to Saba, St. Barths, St. Kitts and Nevis, and Anguilla. The Bahamas Out Islands are another potential destination, especially around the Abacos.

In the U.S. Virgin Islands, St. Thomas and St. John are a mere stone's throw from each other, and the British Virgin Islands are easily reached from either Note that you'll need a passport to move between the two. Within the BVI there are an amazing array of islands you can work into a charter itinerary, including private island resorts, beach bars, and the Baths, one of the most dramatic beach spots in the Caribbean. 

The Grenadines includes the big island of St. Vincent (including quiet Wallilabou Bay, where Pirates of the Caribbean was filmed), Bequia, Carriacou, Union Islands, and several private islands, including the luxurious Palm Island and Petit St. Vincent.

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Who to Charter With

Yacht in Caribbean

cdwheatley / Getty Images

There are many yacht-chartering options in the Caribbean, ranging from individual owners who will happily serve as captain and crew and take you around the islands on their boat to big companies that have fleets of boats available for bareback, crewed, or learn-to-sail journeys.

For example, The Moorings is one of the largest charter companies with operations in the BVI, St. Thomas, Grenada, St. Martin, and St. Lucia. Sunsail is another charter company that has bases in these destinations as well as Antigua, Belize, and the Bahamas.

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Captain or No Captain?

Yachts in BVI

Bob Curley

Can you sail? Can you do it well enough to be entrusted with an unfamiliar boat in unfamiliar waters? If so, then you could consider a bareback charter, but you will need to have a sailing license or be able to show sufficient proof of your sailing experience.

For the rest of us landlubbers, the only option is to sign up for a crewed charter—even if that "crew" means only one captain. Hired captains will also act as a tour guide, historian, and possibly an occasional drinking companion when you want one. Most importantly, they can offer invaluable advice and help you plan an itinerary that suits your interests.

What your captain won't be is a chef or a waiter, so you'll need to bring your own food, prepare it yourself, and clean up after your own messes. If this sounds unappealing, you could opt for additional crew members to do those jobs, but it will cost more. At the end of your trip, you'll be expected to tip.

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What Kind of Boat Should You Charter?

Moorings 4800

Bob Adams / Flickr / CC by 2.0

Your chartering options include sailing yachts and power yachts, although that's a bit of a misnomer, since the sailing yachts also are powered. For the sheer thrill of sailing, you can beat a monohull yacht—the Moorings 54.5 can carry up to 11 passengers—but for comfort and smooth sailing go for a catamaran. These boats tend to be spacious and stable with plenty of room for large groups.

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Tips for Chartering a Boat in the Caribbean

BVI sunset

Bob Curley

  • You need to provision your boat: that means stocking it up with enough food, drinks, and alcoholic beverages for the length of your trip. Start by bringing whatever you can from home. Depending on where you're sailing from, there may be local markets where you can pick up supplies. Generally, ports of call, marinas, and resorts catering to boaters will have at least some food shopping options.
  • As mentioned, set aside some money to tip your captain: 15 to 20 percent of the cost of the charter is customary. Also, remember to buy adequate provisions for your captain, as well!
  • Plan your itinerary in advance. Your captain can help you fine tune your trip, but it's helpful to have a general idea about where you want to go in advance. In addition to sailing distance, you'll need to factor in things like the availability of overnight moorings in your planning.
  • Avoid overpacking. Charter yacht cabins are small, and you'll likely spend most of your days in a bathing suit and t-shirts. A single, soft-sided carry-on should be more than big enough for a week on a yacht, even if you bring one nice outfit for a special dinner ashore.
  • Use nature's clothes dryer: simply pin your wet clothing up on the rail of your yacht and let the tropical breeze do the work.
  • Don't forget your sunscreen and power cords for your mobile devices and speakers (yes, there are power outlets onboard, but they only work when the generator is on).
  • Bring inflatable water toys from home so you have something to play with, along with snorkel equipment.
  • Remember to bring your passport and other necessary travel documents aboard if your itinerary involves crossing international borders.
  • If you need to stay connected, rent a portable Wi-Fi hotspot for the duration of your trip.
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