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Sailing Vacations in the Caribbean

Caribbean
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Caribbean
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Pool
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2 Adults
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1 Bedroom
250 yd to water

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 Water Island
Jul 10 - Jul 17
$200 per night
Boat ∙ 4 guests ∙ 2 bedrooms

Boat in Water Island with Pool & Patio

4.9
Outstanding (10 ratings)
Water Island, St. Thomas, U.S. Virgin Islands
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Boat Isla Grande
Feb 9 - Feb 16
$135 per night
Boat ∙ 2 guests ∙ 5 bedrooms

Entire Boat in Isla Grande with Patio

3.7
Good (12 ratings)
Isla Grande, Santurce, Puerto Rico
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Boat Isla Grande
Feb 9 - Feb 16
$175 per night
Boat ∙ 3 guests ∙ 1 bedroom

Entire Boat in Isla Grande with Patio

Isla Grande, Santurce, Puerto Rico
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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 Saint Mary
Feb 26 - Mar 5
$155 per night
Boat ∙ 5 guests ∙ 3 bedrooms

Boat in Saint Mary with Patio & Pool

3.0
(2 ratings)
Saint Mary, Antigua and Barbuda
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Boat St. Thomas
Jun 25 - Jul 2
$711 per night
Boat ∙ 6 guests ∙ 3 bedrooms

Boat in St. Thomas with Grill & Patio

5.0
Outstanding (4 ratings)
St. Thomas, U.S. Virgin Islands
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Boat Saint-Francois
Oct 7 - Oct 14
$256 per night
Boat ∙ 4 guests ∙ 2 bedrooms

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

4.5
Excellent (8 ratings)
Saint-Francois, Grande-Terre, Guadeloupe
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Information about Sailing Vacations in the Caribbean

🏡 Sailing Vacations available 197 rentals
🌙 Nightly prices starting at $46
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 17 homes
🏊 Sailing Vacations with pools 43 homes

Frequently Asked Questions

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

HomeToGo offers ideal vacation homes, with rates as low as $46 per night.

Sailing Vacations in the Caribbean: are there many vacation rentals available for groups of guests?

The average size for a Houseboat rental is 116 m² and may fit 8 guests on average which is ideal for large groups.

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