A guide to booking Caribbean boat charters

Why settle for just one Caribbean paradise when you could have two, three, four, or more packed into the same vacation? From the nutmeg plantations of Grenada to the pink-tinged beaches of Bermuda, this whole sun-splashed region will be your oyster when you snag your own set of sails. This guide has information on what to expect, some of the hottest destinations, and tips on what sort of globetrotters will feel right at home on the open waves… 

Different types of Caribbean boat charters explained

Not all Caribbean sailing charters are the same. In fact, navigating the lingo, the jargon, and the various multi-hulled and single-hulled vessels can be almost as tricky as conquering the sloshing oceans themselves. The pointers below should help you settle on the right type of craft with the right level of service.

A sailboat charter in the Caribbean with a skipper

If you're not ready to don your captain's uniform just yet, choosing a Caribbean sailing charter package that comes with a skipper might be a good idea. You'll welcome a trained helmsman on board for the duration of your trip, and they'll be responsible for ensuring all the technicalities of sailing and navigation are taken care of. It's also possible to secure boats with a complete crew. You know, just in case you wanted to focus on sipping pina coladas and soaking up the rays.

Bareboat Caribbean sailing charters

At the other end of the spectrum from skippered Caribbean boat charters is the bareboat. Just as the name implies, this is the vessel and nothing else. You'll be responsible for manning the sails and mapping your charts. It's extra pressure but offers extra freedom. 

Get a bareboat charter in the Caribbean

If you're not sure a single-hulled ship will have all the space you need, there's a chance that a catamaran could come to the rescue. With dual keels, these tend to have more square footage on board, fitting in bunks, kitchenettes, larger al fresco areas, and so on. Their design also makes for a stable ride, so you can clink beers after long days on the ocean without worrying they'll spill.

Amazing destinations for Caribbean sailing charters

The Caribbean is a vast and exciting region. It ranges from the dusty ABC isles near Venezuela all the way to the sloshing Sargasso Sea and the shimmering coast of Florida. The destination tips below can help you pinpoint the island that's right for your Caribbean sailing odyssey…

The Bahamas are as stunning as ever

Ah, the Bahamas. Even a mention of the name conjures images of a jet-setter paradise that's laced with cotton-white sands and lapped by turquoise seas. What's more, getting around by boat has been mainstream here ever since Christopher Columbus himself pressed footprints into the sands of San Salvador. Nassau and Freeport, on Grand Bahama, are good places to seek out a ship, but you won't want to miss the rose-tinted powder of Great Exuma, either.

The BVI and the USVI

Ask any veteran of sailboat rentals in the Caribbean and they'll tell you – the USVI and the BVI are up there with the very best places to get on board. There's free movement of vessels between the two, which together combine to offer lush rainforest vistas and gorgeous beaches – the Baths and the remote inlets of Saint Thomas where pirates used to hide are among the highlights.

Consider Saint Vincent and the Grenadines 

Saint Vincent and the Grenadines represents something of a more off-the-beaten-track sailing mecca. Located close to the end of the Lesser Antilles, they are home to pristine coral reefs that are only reachable by boat – check out the Tobago Cays. And when you're on land? Wild carnival festivals and the soaring summit of mighty La Soufriere Volcano mean there's plenty to keep you occupied.

Travelers who will love Caribbean sailing charters

Not sure if a Caribbean sailing charter is the journey for you this year? Read on for a glimpse of the type of globetrotters who often can't wait to get on board and hoist the main sail…

Family catamaran rental in the Caribbean

Larger sailboat rentals in the Caribbean often have enough room to host a whole crew, along with uncles, cousins, and tag-along friends. You might need to make use of below-deck bunk quarters, but there's something special about the comradery and adventure that's built by navigating your own family ship across the wavy ocean.

Adventure-hungry travelers

If you love not knowing where next or can't stand not being able to explore the next cove around the headland, sailboat charters in the Caribbean have all the spontaneity and spirit of exploration you could want. Spotted a white-sand beach in the distance? Plot the course. Want to moor up in that charming fishing village for a mahi mahi and jackfruit? Prepare the anchor. The region is at your fingertips.