Charter a sailboat in Caribbean with or without a captain

319 boats available in Caribbean

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George
George

Great staff. Boat and our experience was perfect.

Marco
Marco

Top charter company. Very friendly and customer oriented

The community's advice on the destination

Sulsana
Sulsana
Not having any specific ideas but not wanting to be in touristy places, he was able to offer us a special place where there was just us...
N’ayant pas d’idées précises mais ne souhaitant pas être dans les endroits touristiques, il a su nous proposer un endroit à part où il n’y avait que nous…
Les Trois-Îlets
Elise
Elise
We left from Marie Galante, then we went to Petite Terre… incredible! We saw lots of turtles, a leopard ray and barracudas. Then we left for Saint François and on the way we saw dolphins! Then we returned to Marie Galante. I highly recommend Petite Terre!!
Nous sommes parties de marie galante, puis nous sommes allées à petite terre … incroyable ! Nous avons vu des tas de tortues, une raie léopard et des barracudas. Ensuite nous sommes parties vers saint François et en route nous avons vues des dauphins! Puis nous sommes rentrées à marie galante . Je recommande très fortement petite terre !!
Saint-François
Gaetan
Gaetan
We sailed in the Guadeloupe archipelago: Marie-galante and the Saintes The playground is truly fantastic
Nous avons navigué dans l’archipel de Guadeloupe : Marie-galante et les Saintes Le terrain de jeu est vraiment fantastique
Bas du Fort
Cyril
Cyril
Great sailing. We did even more than what was planned.
Superbe navigation. Nous avons fait même plus que ce qui y était prévu.
Les Trois-Îlets
Keith
Keith
Take it for more than a day! So much to see!
Nassau
Carolina
Carolina
Jost Van Dyke and Bitter End
Parham Town
John
John
St. Thomas and St John are beautiful and can easily fill a 7 day charter.
Saint Thomas
Rebecca
Rebecca
Great cruising area. We loved tintamare and fourchu. Check in and check out every time we change islands is a waste of time. We decided to do only 2 islands and not go to Anguilla because of that.
Anse Marcel

Sail Away: Sailboat rental in the Caribbean for your next adventure

The Caribbean offers a paradise with its crystal-clear waters, steady trade winds, and breathtaking scenery. A sailboat rental Caribbean adventure provides the freedom to explore multiple islands at your own pace. Unlike traditional vacations, sailing vacation experiences allow you to wake up to different stunning views each morning.

The Caribbean sailing experience combines luxury, adventure, and relaxation in a way few other vacation styles can match. Life aboard a sailboat connects you with the sea in a uniquely intimate way.

Choosing the right sailboat rental

When planning your Caribbean yacht charter, selecting the appropriate sailboat is crucial. Consider factors like:

  • crew size;
  • sailing qualifications;
  • experience level.

For those new to sailing, captained charters provide a knowledgeable captain who handles navigation while you relax and enjoy the journey.

Experienced sailors might prefer a bareboat charter, giving complete control over their island-hopping adventure. Caribbean sailboat charter options range from compact 30-foot boats ideal for couples to spacious yachts for larger groups, complete with Wi-Fi and upscale amenities.

Costs and budgeting for renting a sailboat in the Caribbean

Budget considerations for Caribbean sailing vacations vary widely depending on several factors. High season (December through April) typically commands premium rates, while the wet season offers substantial savings. Your sailboat's size, trip length, destinations, and choice of crewed or bareboat charter all influence the total cost.

Most transactions are in USD, though some locations use the East Caribbean dollar. Remember to budget for extras like provisioning, mooring fees, and activities like snorkeling or fishing during your cruise. Your time aboard should be about enjoyment, not worry over unexpected expenses.

Licensing for sailboat rental in the Caribbean?

Most Caribbean yacht charter companies require proof of sailing experience or sailing qualifications before allowing you to rent their sailboats. Requirements vary by location and boat size, but typically, an experienced sailor with documented time as captain will face few obstacles.

Those without formal certification might need to demonstrate competency through a brief skills assessment. Fortunately, many Caribbean routes offer easy line-of-sight navigation, making the region suitable for sailors of all experience levels.

Top destinations in the Caribbean islands

The Caribbean region offers diverse sailing conditions and destinations. The British Virgin Islands and the Virgin Islands are perfect for beginners with protected waters and short distances between stops. The Leeward Islands, including St. Martin, offer a mix of French and Dutch culture.

For more challenging sailing, the Windward Islands stretch from St. Lucia to Grenada, the famous spice island. Be sure to visit Virgin Gorda's dramatic granite boulders and the Tobago Cays Marine Park, known for world-class snorkeling and thriving marine life. Jolly Harbour in Antigua provides excellent facilities for sailors looking to visit multiple islands in comfort.

Caribbean sailing vacations: culture and events

Beyond white sand beaches and beach bars, the Caribbean offers rich local culture and events worth planning your itinerary around. From food festivals in Grenada to sailing regattas throughout the islands, there's always something happening on the sea.

Many sailors discover hidden coves inaccessible to large cruise yachts, where you can experience life more authentically and explore local communities away from tourist crowds.

Tips for a successful sailboat rental experience

The perfect destination deserves perfect planning. Book your Caribbean charter well in advance, especially for high season. Research typical sailing conditions and trade winds for your chosen islands.

Pack light, but don't forget essentials like reef-safe sunscreen, a hat, and non-marking boat shoes. Most importantly, remain flexible – sometimes the best adventures come from discovering an unplanned anchorage or taking time to visit clear waters you happen upon during your sail through this sailor's paradise.

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