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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

Boat Saint-Francois
Mar 25 - Apr 1
$392 per night
Boat ∙ 4 guests ∙ 2 bedrooms
Boat in Saint-Francois
4.7
"Outstanding" (65 ratings)
Saint-Francois, Saint-Francois, Guadeloupe
Details
FlipKey
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Boat Nassau
Mar 31 - Apr 7
$254 per night
Boat ∙ 4 guests ∙ 2 bedrooms
Boat in Nassau
Nassau, New Providence, The Bahamas
Details
Vrbo
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Boat Parham Town
Aug 12 - Aug 19
$3,850 per night
Boat ∙ 4 guests ∙ 1 bedroom
Boat in Parham Town with Patio
Parham Town, Tortola, British Virgin Islands
Details
Expedia
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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-Francois
Sep 16 - Sep 23
-39%
$461
$283 per night
Boat ∙ 4 guests ∙ 1 bedroom
Boat in Saint-Francois with Patio & Grill
4.5
"Outstanding" (16 ratings)
Saint-Francois, Grande-Terre, Guadeloupe
Details
Expedia
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Boat Black Point
Apr 2 - Apr 9
$2,905 per night
Boat ∙ 4 guests ∙ 3 bedrooms
Pleasant Boat in Black Point
Black Point, The Bahamas
Details
Vrbo
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Boat Saint George's
May 6 - May 13
$1,368 per night
Boat ∙ 6 guests ∙ 4 bedrooms
Boat in Saint George\'s
5.0
"Excellent" (3 ratings)
Saint George's, Saint George, Grenada
Details
FlipKey
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Frequently Asked Questions

Sailing Vacations in the Caribbean: How much does it cost to rent a vacation rental in the Caribbean?

HomeToGo has incredible rentals for Sailing Vacations in the Caribbean, with retes as low as $20 per night.

Can I find a vacation rental for a group of guests for Sailing Vacations in the Caribbean?

House boat rental in the Caribbean can fit 6 guests.

What types of vacation homes can I find for Sailing Vacations in the Caribbean?

There are many House boat rental and House rental that are great for Sailing Vacations in the Caribbean.

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