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Sailing Vacations in the Caribbean

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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
Jan 20 - Jan 27
$261 per night
Boat ∙ 6 guests ∙ 3 bedrooms
Boat in Calvin Hill with Grill
5.0
Outstanding (12 ratings)
Calvin Hill, Exuma, The Bahamas
Details
Vrbo
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Boat Andros Town
Mar 16 - Mar 23
$408 per night
Boat ∙ 7 guests ∙ 3 bedrooms
Boat in Andros Town + Ocean Views
5.0
Outstanding (4 ratings)
Andros Town, North Andros, The Bahamas
Details
Vrbo
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Boat Southgate Farm
Sep 23 - Sep 30
$149 per night
Boat ∙ 4 guests ∙ 2 bedrooms
Boat in Southgate Farm with Pool
4.6
Excellent (10 ratings)
Southgate Farm, East End, U.S. Virgin Islands
Details
Vrbo
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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 Road Town
Mar 16 - Mar 23
$3,334 per night
Boat ∙ 6 guests ∙ 3 bedrooms
Boat in Road Town
Road Town, Tortola, British Virgin Islands
Details
Vrbo
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Boat Red Hook
Jan 6 - Jan 13
$3,000 per night
Boat ∙ 8 guests ∙ 5 bedrooms
Charming Boat in Red Hook with Grill
5.0
Outstanding (2 ratings)
Red Hook, Saint Thomas, U.S. Virgin Islands
Details
Vrbo
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Boat Bullock Harbour
Apr 13 - Apr 20
$261 per night
Boat ∙ 6 guests ∙ 3 bedrooms
Pleasant Boat in Bullock Harbour with Grill
5.0
Outstanding (16 ratings)
Bullock Harbour, Berry Islands, The Bahamas
Details
Vrbo
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Information about Sailing Vacations in the Caribbean

🏡 Vacation rentals available 148 homes
🌙 Nightly prices starting at $42
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 13 homes
🏊 Vacation rentals with pools 40 homes

Frequently Asked Questions

Sailing Vacations in the Caribbean: What is the vacation rental cost in the Caribbean?

You can get a great vacation rental from $1,348 and find discounts up to 10%!

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

Houseboat rental in the Caribbean may fit 7 people.

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