menu
Destinations
North America
» United States
» Canada
» Mexico
» California
» Florida
» Hawaii
» New York
» Quebec
Regions
» Africa
» Asia
» Australia, NZ & Pacific
» Caribbean
» Central America
» Europe
» Middle East
» South America
Europe
» France
» Ireland
» Italy
» Spain
» United Kingdom
» See All Europe
Elsewhere
» Costa Rica
» Australia
» New Zealand
» Puerto Rico
» India
Vacations
» Accommodations
» Adventure Travel
» Cruises
» Discovery
» Fishing & Hunting
» Health & Wellness
» Local Entertainment
» Nature & Wildlife
» Rentals
» Snow & Ski Vacations
» Tours
» Travel Guides
» Travel Services
Travel Services
» Car Rentals
» RV Rentals
» Shuttle Services
» More...
search
Add Your Listing
Login
Your Account
» Login
» Select Currency (USD$)
» Free Travel Newsletter
About RealAdventures
» About Us
» Advertising Options
» Careers
» DMCA Policy
» Select Currency (USD$)
» Travel Newsletter
» Contact Us
USD $
» US $
» British Pound £
» Canadian $
» Euro €
» Yen ¥
» Other Currency
add
Current Filter
Vacations
(112,201)
Sailing
(316)
Caribbean
(12)
add
Countries
Bahamas
(1)
British Virgin Islands
(2)
Dominican Republic
(1)
Grenada
(1)
Guadeloupe
(1)
Puerto Rico
(5)
Saint Lucia
(1)
add
Top Destinations in Caribbean
search
Castries, Saint Lucia
Christ Church, Barbados
Gros Islet, Saint Lucia
Havana, Cuba
Higuey, Dominican Republic
Kingston, Jamaica
Montego Bay, Jamaica
Nassau, Bahamas
Negril, Jamaica
Ocho Rios, Jamaica
Providenciales, Turks and Caicos Islands
Puerto Plata, Dominican Republic
Punta Cana, Dominican Republic
Runaway Bay, Jamaica
Saint Johns, Antigua and Barbuda
Saint Thomas, US Virgin Islands
San Juan, Puerto Rico
Santo Domingo, Dominican Republic
Trinidad, Cuba
Willemstad, Netherlands Antilles
add
Vacation Ideas inCaribbean
Accommodations
Bed & Breakfasts
(4,243)
Campgrounds & RV Parks
(1,296)
Hotels & Resorts
(71,494)
Vacation Rentals
(2,701)
Youth Hostels
(23,902)
Adventure Travel
ATV Riding & Jeep Tours
(22)
Bike Tours
(280)
Bungee Jumping
(7)
Cave Exploration
(11)
Hang Gliding & Paragliding
(23)
Hiking & Trekking
(663)
Horseback Riding & Dude Ranches
(564)
Hot Air Ballooning
(61)
Kayaking & Canoeing
(233)
Motorcycle Tours
(101)
Rafting Trips
(112)
Rock Climbing
(30)
Sailing
(316)
Scuba Diving & Snorkeling
(332)
Skydiving
(79)
Storm Chasing
(8)
Surfing
(40)
Water Skiing & Jet Skiing
(17)
Windsurfing
(4)
Cruises
Cruises
(353)
Yacht Charters
(12)
Fishing & Hunting
Fishing Trips
(1,856)
Hunting Trips
(430)
Health & Wellness
Day Spa
(8)
Detox & Rejuvenate
(4)
Fitness & Weight Loss
(16)
Health Spas & Retreats
(29)
Spiritual
(10)
Yoga Retreats & Programs
(26)
Local Entertainment
Golf
(18)
Monuments
(1)
Museums
(3)
Music Venue
(1)
Theme Park
(7)
Water Parks
(1)
Nature & Wildlife
Birdwatching
(16)
Camel Riding
(16)
Eco Tours
(233)
Whale Watching
(69)
Wildlife & Safari Tours
(372)
Personal Growth & Educational
Archaeology
(5)
Artisan & Trade Workshops
(13)
Cooking Classes & Wine Tasting
(73)
Cultural Experience
(29)
Folk Medicine
(1)
Gold Prospecting
(1)
Language Schools
(50)
Museums & Art Galleries
(13)
Personal Growth
(4)
Photography Workshops
(10)
Summer Camps & Programs
(19)
Volunteer Vacations
(21)
Wine Tasting
(1)
Rentals
Bicycle Rentals
(4)
Canoe & Kayak Rentals
(15)
Car Rentals
(61)
Jetski & Watercraft Rentals
(1)
Motorcycle Rentals
(11)
RV Rentals
(110)
Sailboat & Yacht Rentals
(4)
Snow & Ski Vacations
Dog Sledding
(15)
Skiing & Snowboarding
(28)
Snowmobiling
(16)
Snowshoeing
(6)
X-Country Skiing
(1)
Tours
Scenic Flights
(138)
Sight-Seeing Tours
(1,436)
Train Tours
(17)
Travel Guides
Articles
(171)
Maps
(42)
Official Info
(16)
Photography
(24)
Travel Services
Car & Van Shuttle Service
(77)
Destination Weddings
(13)
Passport & Visas
(3)
Reservations
(30)
Tourism Center
(106)
Travelers Checks
(13)
For Members Only!
Looking for the hottest travel deals? Join the RealAdventures community and get a free travel newsletter full of ideas, hot deals and more.
See latest edition
.
Sign-Up Today »
Travel Providers
Add Your Travel Services
Update Your Listing
About RealAdventures
About Us
DMCA Policy
Select Currency (USD$)
Contact Us
Top Sailing Vacations in Caribbean
| Trips, Rentals & Lessons
»
Vacations
(112,201)
»
Sailing
(316)
swap_horiz
»
Caribbean
(12)
tune
Filters
auto_awesome
Vacations
& Adventures
Region
place
Country
Top Cities
Accommodations
Bed & Breakfasts
(4,243)
Campgrounds & RV Parks
(1,296)
Hotels & Resorts
(71,494)
Vacation Rentals
(2,701)
Youth Hostels
(23,902)
Adventure Travel
ATV Riding & Jeep Tours
(22)
Bike Tours
(280)
Bungee Jumping
(7)
Cave Exploration
(11)
Hang Gliding & Paragliding
(23)
Hiking & Trekking
(663)
Horseback Riding & Dude Ranches
(564)
Hot Air Ballooning
(61)
Kayaking & Canoeing
(233)
Motorcycle Tours
(101)
Rafting Trips
(112)
Rock Climbing
(30)
Sailing
(316)
Scuba Diving & Snorkeling
(332)
Skydiving
(79)
Storm Chasing
(8)
Surfing
(40)
Water Skiing & Jet Skiing
(17)
Windsurfing
(4)
Cruises
Cruises
(353)
Yacht Charters
(12)
Fishing & Hunting
Fishing Trips
(1,856)
Hunting Trips
(430)
Health & Wellness
Day Spa
(8)
Detox & Rejuvenate
(4)
Fitness & Weight Loss
(16)
Health Spas & Retreats
(29)
Spiritual
(10)
Yoga Retreats & Programs
(26)
Local Entertainment
Golf
(18)
Monuments
(1)
Museums
(3)
Music Venue
(1)
Theme Park
(7)
Water Parks
(1)
Nature & Wildlife
Birdwatching
(16)
Camel Riding
(16)
Eco Tours
(233)
Whale Watching
(69)
Wildlife & Safari Tours
(372)
Personal Growth & Educational
Archaeology
(5)
Artisan & Trade Workshops
(13)
Cooking Classes & Wine Tasting
(73)
Cultural Experience
(29)
Folk Medicine
(1)
Gold Prospecting
(1)
Language Schools
(50)
Museums & Art Galleries
(13)
Personal Growth
(4)
Photography Workshops
(10)
Summer Camps & Programs
(19)
Volunteer Vacations
(21)
Wine Tasting
(1)
Rentals
Bicycle Rentals
(4)
Canoe & Kayak Rentals
(15)
Car Rentals
(61)
Jetski & Watercraft Rentals
(1)
Motorcycle Rentals
(11)
RV Rentals
(110)
Sailboat & Yacht Rentals
(4)
Snow & Ski Vacations
Dog Sledding
(15)
Skiing & Snowboarding
(28)
Snowmobiling
(16)
Snowshoeing
(6)
X-Country Skiing
(1)
Tours
Scenic Flights
(138)
Sight-Seeing Tours
(1,436)
Train Tours
(17)
Travel Guides
Articles
(171)
Maps
(42)
Official Info
(16)
Photography
(24)
Travel Services
Car & Van Shuttle Service
(77)
Destination Weddings
(13)
Passport & Visas
(3)
Reservations
(30)
Tourism Center
(106)
Travelers Checks
(13)
United States
(216)
Canada
(27)
Mexico
(5)
Africa
(2)
Asia
(14)
Australia, NZ & Pacific
(2)
Caribbean
(12)
Central America
(2)
Europe
(31)
Middle East
(5)
North America
(248)
Bahamas
(1)
British Virgin Islands
(2)
Dominican Republic
(1)
Grenada
(1)
Guadeloupe
(1)
Puerto Rico
(5)
Saint Lucia
(1)
Top Destinations in Caribbean
search
Castries, Saint Lucia
Christ Church, Barbados
Gros Islet, Saint Lucia
Havana, Cuba
Higuey, Dominican Republic
Kingston, Jamaica
Montego Bay, Jamaica
Nassau, Bahamas
Negril, Jamaica
Ocho Rios, Jamaica
Providenciales, Turks and Caicos Islands
Puerto Plata, Dominican Republic
Punta Cana, Dominican Republic
Runaway Bay, Jamaica
Saint Johns, Antigua and Barbuda
Saint Thomas, US Virgin Islands
San Juan, Puerto Rico
Santo Domingo, Dominican Republic
Trinidad, Cuba
Willemstad, Netherlands Antilles
Page 1 of 1
Sort By
Featured
Most Popular
Price: Low to High
Price: High to Low
Newly Listed
Updated Recently
Expires First
Most Viewed (asc)
Most Viewed (desc)
Date Viewed (asc)
Date Viewed (desc)
Accessed (asc)
Accessed (desc)
Expires (asc)
Expires (desc)
Inquiry (asc)
Inquiry (desc)
stars
Private Sail Boat Charters Puerto Rico
Ceiba, Puerto Rico
Sail, snorkel, shine, relax aboard the Katarina
Rincon, Puerto Rico
Sailing Charters in Dominican Republic
Casa de Campo, Dominican Republic
Classic Sail Charters - Puerto Rico
Fajardo, Puerto Rico
Day sail trip St.Lucia with spaghetti lunch
Rodney Bay, Saint Lucia
Sail The Caribbean On A Private Yacht
Belfast, Puerto Rico
Imagine a new sea view each morning.....
Exuma, Bahamas
Puerto Rico Boat Rentals & Island Hopping
Fajardo, Puerto Rico
Sailing in Guadeloupe
Jarry, Guadeloupe
Luxury Yacht Charters With Crew
Road Town, British Virgin Islands
Motu Catamaran Yacht for BVI
Smugglers Cove, British Virgin Islands
Learn to Sail and Have a Vacation in The Caribbean
St George's, Grenada
Add Your Travel Services and Accommodations
Create a listing on RealAdventures and be seen by millions of travelers making plans for their next vacation.
More Sailing Around the World
(show all)
Vancouver Luxury Yacht Charters
Vancouver, British Columbia
Day Sailing & Custom Charters On The Schooner Olad
Camden, Maine
NCP Charter (NCP&mare)
Sibenik, Croatia
Kootenay Lake Sailing Charters Canada
Crawford Bay, British Columbia
Rainy Lake Houseboats premier houseboat rentals
International Falls, Minnesota
Bareboat yacht charters Pacific North West, Canada
Nanaimo, British Columbia
Custom Sailing Charters from Rockland, Maine
Rockland, Maine
The Best Choise For Your Cruise In Croatia
Dubrovnik, Croatia
Turkey Sailing Blue Voyages & Blue Cruises
Bodrum, Turkey
Sailing In Mediterranean With Medsail Holidays
Aegean Islands, Greece
Top Listings in Caribbean
(show all)
Eco-friendly Barbados Chi Centre Guest House
St. Michael, Barbados
Vacation Rentals
Llantrissant - A Negril Beachhouse
Negril Jamaica, Jamaica
Vacation Rentals
Big Marlin Fishing Charters In Punta Cana
Punta Cana, Dominican Republic
Fishing Trips
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
Pure Adventure
Fajardo, Puerto Rico
Eco Tours
Oceanfront Vacation Villa in St. Maarten
Anse-Marcel, Saint Martin
Vacation Rentals
Ocean Cliff Hotel Negril
Negril, Jamaica
Hotels & Resorts
St.lucia
Cap Estate, Saint Lucia
Vacation Rentals
Vacation Villas with BONEFISHING and DIVING
Grace Bay, Turks and Caicos Islands
Vacation Rentals
Add Your Travel Services and Accommodations
Create a listing on RealAdventures and be seen by millions of travelers making plans for their next vacation.
Create Your Listing
1
Also in Caribbean
Accommodations
Bed & Breakfasts
(264)
Campgrounds & RV Parks
(1)
Hotels & Resorts
(900)
Vacation Rentals
(224)
Youth Hostels
(113)
Adventure Travel
Bike Tours
(3)
Hiking & Trekking
(1)
Horseback Riding & Dude Ranches
(2)
Kayaking & Canoeing
(2)
Sailing
(12)
Scuba Diving & Snorkeling
(15)
Skydiving
(1)
Fishing & Hunting
Fishing Trips
(7)
Health & Wellness
Health Spas & Retreats
(2)
Nature & Wildlife
Eco Tours
(7)
Personal Growth & Educational
Cooking Classes & Wine Tasting
(3)
Top Sailing Vacations in Caribbean
| Trips, Rentals & Lessons
Browse incredible sailing vacations & trips in Caribbean, take a lesson or rent your own sail boat. Browse our sailing options in Caribbean and plan your vacation. Also of Interest:
boat charter
|
charter sailing
|
charter yacht
|
private sail
|
private sailing
|
Get Your Free RealAdventures Travel Newsletter
Get your free travel newsletter full of inspiring travel ideas, great deals, destinations and adventures. Discover new places to explore, new adventures and new experiences.
See latest edition
.
Sign-Up Today »