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Sailing Vacations in the Caribbean

Caribbean
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$100 - $199
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Sailing Vacations in the Caribbean

Sailing vacations in the Caribbean are ideal for those who want to indulge in relaxation while enjoying crystal clear waters.

Sailing Vacations in the Caribbean: Top Accommodations

Apartment East End
$177 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.8
"Excellent" (20 ratings)
East End, Saint Thomas, U.S. Virgin Islands
Details
Vrbo
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House Coral Bay
$458 per night
House ∙ 6 guests ∙ 3 bedrooms
Coral Bay, St. John, U.S. Virgin Islands
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Villa East End
$542 per night
Villa ∙ 4 guests ∙ 2 bedrooms
East End, Saint Thomas, U.S. Virgin Islands
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4 Best Cruising Destinations in the Caribbean

4 Best Cruising Destinations in the Caribbean

Cruising through Antigua, the Bahamas, the British Virgin Islands, and Cuba, enables travelers to explore the passages between Grenada and Saint Vincent. Caribbean cruise passengers also have the opportunity to make stopovers along the 700 Islands of the Bahamas.

  • Antigua

    You will get to enjoy a host of water-related activities at Antigua. Consider Antigua, the sailor's heaven on earth. Best of all, you do not have to be an expert to enjoy the water.

  • The British Virgin Islands

    You will be able to access some of the best sailing destinations in the Caribbean at the British Virgin Islands. Sail at sites such as RMS Rhone, the shores of Anegad, Smuggler's Cove on Tortola, and Cane Garden Bay. You can also enjoy the evening at some of the local watering holes.

  • Cuba

    Boasting 3,500 miles (5,700 kilometers) of coastline and unexplored coral reefs, Cuba has endless offerings for cruise passengers. Make time to visit Old Havana and Trinidad, which are both UNESCO World Heritage Sites. Brush up on your knowledge of local history at the Hemingway Museum and interact with flora and fauna at Topes de Collantes National Park. When you finish the day's activities, drink and dance at the local restaurants and bars.

  • The Bahamas

    The Bahamas, southeast of Florida, consists of coral islands and shallow water. The island nation makes for smooth sailing, and tourists will have the option of relaxing at countless beaches. Go for a shopping trip at Nassau, see the hammerhead sharks at Atlantis Paradise Island or go for a boat ride at Exuma Cays Land and Sea Park.

Best Places to Stay for Sailing Vacations in the Caribbean

House Frederiksted
$121 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (1 rating)
Frederiksted, St. Croix, U.S. Virgin Islands
Details
Vrbo
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Apartment Bolongo
$125 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.6
"Outstanding" (75 ratings)
Bolongo, Southside, U.S. Virgin Islands
Details
Vrbo
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House Le Gosier
$24 per night
House ∙ 3 guests ∙ 2 bedrooms
Le Gosier, Grande-Terre, Guadeloupe
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Vrbo
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Frequently Asked Questions

How much do vacation rentals for Sailing Vacations in the Caribbean cost?

HomeToGo has incredible rentals for Sailing Vacations in the Caribbean, with prices as low as $19 per night.

What kinds of rentals can I find for Sailing Vacations in the Caribbean?

There are many Apartment rentals and Hotel rooms that are great for Sailing Vacations in the Caribbean.

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