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Sailing Vacations in the Caribbean

Caribbean
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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

Boat Calvin Hill
Mar 16 - Mar 23
$261 per night
Boat ∙ 6 guests ∙ 3 bedrooms

Boat in Calvin Hill with Grill & Patio

5.0
Outstanding (16 ratings)
Calvin Hill, Exuma, The Bahamas
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Boat Saint-Francois
Mar 23 - Mar 30
$231 per night
Boat ∙ 4 guests ∙ 2 bedrooms

Boat in Saint-Francois with Grill & Patio + Lagoon Views

4.4
Very good (7 ratings)
Saint-Francois, Grande-Terre, Guadeloupe
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Boat Water Island
Jun 1 - Jun 8
$200 per night
Boat ∙ 4 guests ∙ 2 bedrooms

Boat in Water Island with Pool & Patio

4.7
Excellent (7 ratings)
Water Island, St. 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.

  • 1. 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.

  • 2. 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.

  • 3. 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.

  • 4. 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

Boat Southgate Farm
Apr 13 - Apr 20
$149 per night
Boat ∙ 4 guests ∙ 2 bedrooms

Boat in Southgate Farm with Pool & Patio

4.4
Very good (11 ratings)
Southgate Farm, East End, U.S. Virgin Islands
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Boat George Town
Aug 17 - Aug 24
$289 per night
Boat ∙ 5 guests ∙ 1 bedroom

Boat in George Town

5.0
Outstanding (9 ratings)
George Town, Exuma, The Bahamas
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Boat Union Vale
Apr 13 - Apr 20
-84%
$800
$125 per night
Boat ∙ 4 guests ∙ 2 bedrooms

Beautiful Boat in Union Vale with Grill & Patio

5.0
Outstanding (2 ratings)
Union Vale, Port Elizabeth, Saint Vincent and the Grenadines
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Information about Sailing Vacations in the Caribbean

🏡 Sailing Vacations available 196 rentals
🌙 Nightly prices starting at $45
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 18 homes
🏊 Sailing Vacations with pools 43 homes

Frequently Asked Questions

Sailing Vacations in the Caribbean: What is the cost per night of stay?

HomeToGo has incredible rentals for Sailing Vacations in the Caribbean, with prices as low as $45 per night.

Can I find a vacation home for a group for Sailing Vacations in the Caribbean?

in the Caribbean, large groups should look for Houseboat rental since they fit 8 people.

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