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Private Sail Boat Charters Puerto Rico | Ceiba, Puerto Rico | Sailing
Classic Sail Charters - Puerto Rico | Fajardo, Puerto Rico | Sailing
Day sail trip St.Lucia with spaghetti lunch | Rodney Bay, Saint Lucia | Sailing
Sail The Caribbean On A Private Yacht | Belfast, Puerto Rico | Sailing
Sailing Charters  in Dominican Republic | Casa de Campo, Dominican Republic | Sailing

Sailing Charters in Dominican Republic

Casa de Campo, Dominican Republic
Imagine a new sea view each morning..... | Exuma, Bahamas | Sailing
Puerto Rico Boat Rentals & Island Hopping | Fajardo, Puerto Rico | Sailing
Sailing in Guadeloupe | Jarry, Guadeloupe | Sailing

Sailing in Guadeloupe

Jarry, Guadeloupe
Luxury Yacht Charters With Crew | Road Town, British Virgin Islands | Sailing

Luxury Yacht Charters With Crew

Road Town, British Virgin Islands
Motu Catamaran Yacht for BVI | Smugglers Cove, British Virgin Islands | Sailing

Motu Catamaran Yacht for BVI

Smugglers Cove, British Virgin Islands
Learn to Sail and Have a Vacation in The Caribbean | St George's, Grenada | Sailing

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More Sailing Around the World (show all)
Private appartment at Ski Resort CRANS MONTANA | Crans Montana, Switzerland | Sailing
Kootenay Lake Sailing Charters Canada | Crawford Bay, British Columbia | Sailing

Kootenay Lake Sailing Charters Canada

Crawford Bay, British Columbia
Rainy Lake Houseboats  premier houseboat rentals | International Falls, Minnesota | Sailing

Rainy Lake Houseboats premier houseboat rentals

International Falls, Minnesota
Bareboat yacht charters Pacific North West, Canada | Nanaimo, British Columbia | Sailing
The Best Choise For Your Cruise In Croatia | Dubrovnik, Croatia | Sailing
Sailing In Mediterranean With Medsail Holidays | Aegean Islands, Greece | Sailing
Joy Ride Charters | Westbrook, Connecticut | Sailing

Joy Ride Charters

Westbrook, Connecticut
Empowerment Adventures For Women | Nanaimo, British Columbia | Sailing

Empowerment Adventures For Women

Nanaimo, British Columbia
Top Listings in Caribbean (show all)
Pure Adventure | Fajardo, Puerto Rico | Eco Tours

Pure Adventure

Fajardo, Puerto Rico
Eco Tours
Eco-friendly Barbados Chi Centre Guest House | St. Michael, Barbados | Vacation Rentals

Eco-friendly Barbados Chi Centre Guest House

St. Michael, Barbados
Vacation Rentals
Llantrissant - A Negril Beachhouse | Negril Jamaica, Jamaica | Vacation Rentals

Llantrissant - A Negril Beachhouse

Negril Jamaica, Jamaica
Vacation Rentals
Charming 2 Bed/2 Bath Villa With Hot Tub And Views | Cruz Bay, US Virgin Islands | Vacation Rentals

Charming 2 Bed/2 Bath Villa With Hot Tub And Views

Cruz Bay, US Virgin Islands
Vacation Rentals
Accommodation In Havana, Cuba. 3-room Apartment. | La Habana, Cuba | Vacation Rentals

Accommodation In Havana, Cuba. 3-room Apartment.

La Habana, Cuba
Vacation Rentals
Amazing Barbados Vacation Rentals | West, Barbados | Vacation Rentals

Amazing Barbados Vacation Rentals

West, Barbados
Vacation Rentals
Big Marlin Fishing Charters In Punta Cana | Punta Cana, Dominican Republic | Fishing Trips

Big Marlin Fishing Charters In Punta Cana

Punta Cana, Dominican Republic
Fishing Trips
Oceanfront Vacation Villa in St. Maarten | Anse-Marcel, Saint Martin | Vacation Rentals

Oceanfront Vacation Villa in St. Maarten

Anse-Marcel, Saint Martin
Vacation Rentals
St.martin/maarten Vacation Villas And More | St. Martin, Saint Martin | Vacation Rentals

St.martin/maarten Vacation Villas And More

St. Martin, Saint Martin
Vacation Rentals
St.lucia | Cap Estate, Saint Lucia | Vacation Rentals

St.lucia

Cap Estate, Saint Lucia
Vacation Rentals


Explore Over 100 Travel Categories To Find Your Next Amazing Vacation

With a diverse array of more than 100 travel categories and options, finding the ideal vacation is a breeze. Whether you are looking for a cozy cabins, luxurious resorts, thrilling adventure tours, or tranquil beach getaways, we have the perfect travel option waiting for you.

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  • Destination Weddings
  • Passenger Ferry
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  • Travelers Checks


Top Caribbean Sailing Vacations | Trips, Rentals & Lessons

Browse incredible Caribbean sailing vacations & trips, take a lesson or rent your own sail boat. Browse our Caribbean sailing options and plan your vacation. Also of Interest: boat charter | charter sailing | charter yacht | private sail | private sailing |