Private yacht sailing holidays with skipper in the Caribbean

Private yacht sailing holidays with skipper in the Caribbean

Discover the magic of sailing holidays in the Caribbeans! Renting a sailing boat: a new way of traveling with your loved one, your friends or your family. Find your dream adventure among hundreds of holidays organised by local skippers.

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

Why you should book a holiday with Sailsquare?

Location point above a wave

The leading sailing holiday marketplace

25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.

Two people with sailor hats

Get onboard solo, with your family, or your friends

Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

A boat with a magnifier above it

Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

Two coins with a currency on top

Sailing holidays that suit all budgets

Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!

Reviews - Private yacht sailing holidays with skipper in the Caribbean

1 review
20 / 10
Valentina R.

Valentina R.

review about From Martinique to the Grenadines and Tobago Cays. a warm winter January 2019

10 / 10
We have recently returned from this wonderful journey and we still have in our hearts and eyes the beautiful places we have visited. A huge thank you to the skipper Alessandro who led us with skill, sympathy and a lot of patience in the "perilous" Caribbean waters, infested with barracuda (unfortunately no lampughe or tuna). If you still want us on board with you, we will be there! Thanks also to the co-skipper "zen", the pizza maker "in pectore", Carlo and his partner Mala who cheered us up with his extravagant good humor and his lucullian dishes. Thanks also to the travel companions: Antonella, Carmen, Luisa, Renata, Danilo and Nerino, with whom we shared the holiday in a good mood. Until next time. Valentina and Norberto
Trustpilot

Customer Support

Would you like some support using the platform? We've (almost) always got the answers!

Call us at +44 20351 44220 Check out our Help page

Can't find the perfect holiday for you?

Use our free holiday concierge tool - and let us find your dream sailing experience for you!

Let's find it together!

6 reasons to charter a Caribbean yacht:

  • Enjoy a week of summer during the winter on a Caribbean yacht charter Sailboat in the Caribbean
  • Discover paradisiacal beaches, swim in crystal clear waters and relax under palm trees, away from the tourist crowds
  • Take the Caribbean yacht charter and learn from your skipper during a sailing course
  • Enjoy the comfort and space aboard a sailing yacht or catamaran with your loved ones
  • Rent a catamaran in the Caribbean and enjoy an unforgettable experience on board
  • Sail or catamaran sail with a local skipper and immerse yourself in the culture of your holiday destination

Advantages of yacht charter in the Caribbean:

Caribbean Sailing Yacht Charter

Sailboat charter in the Caribbean is the perfect way to have a great time with family or with a group of friends. Plan your sailing route with your local skipper and enjoy a unique and personalised experience. Your skipper will know how to recommend the most beautiful beaches and the most remote islands to make your dream sailing holiday come true.

Catamaran charter in the Caribbean

Especially in the Caribbean, it's wise to consider chartering a catamaran. In the often shallow waters, a catamaran will allow you to sail smoothly, as it is shallower in the water. Catamaran sailing also means luxury and plenty of space: relax on deck, sleep under the stars on the catamaran's net and discover the breathtaking scenery of the Caribbean.

Everything you need to know about chartering a Caribbean boat:

  • We recommend planning a Caribbean yacht charter in November, February and March, so you can avoid the high season and tourist crowds. Travel to the Caribbean between late May and early November should be avoided as there is an increased risk of hurricanes during this period.
  • The Caribbean is ideal for a relaxing holiday with your family, but a Caribbean yacht charter with friends is also very popular. Choose the experience that best suits your needs from a wide range of offers and enjoy an unforgettable holiday.
  • It's always advisable to plan a two-week holiday to really enjoy the trip and discover all the wonderful places in the area at your leisure.
  • Many Caribbean islands have good connections via international airports and some islands have direct flights from Europe.

The best itineraries for Caribbean yacht charter:

Some examples of itineraries:

  • Route through Bahamas: Marsh Harbour - Elbow Cay - Man O War Cay - Green Turtle Cay - Treasure Cay - Marsh Harbour.
  • Route through Cuba: Cienfuegos - Tiki Bay of Pigs - Isle of Youth - National Park - Cayo Largo - Trinidad - Cayo Cinco Balas - Rancho Luca Beach - Cienfuegos