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Top Caribbean Sailing Trips

262 Results
Private, Skippered Catamaran Day Trip in Grenada

With this 7-hour Day Trip, you will enjoy the most beautiful sights of the south coast of Grenada onboard our luxury catamaran. The boat is …More

With this 7-hour Day Trip, you will enjoy the most beautiful sights of the south coast of Grenada onboard our luxury catamaran. The boat is...

7 hours
4.9 (74)
from
$1,350
Private St. Maarten Cruise - Hakuna Matata Catamaran

Embark on a truly unique journey, where your experience is shaped by your desires. Perfect for families, couples, or groups, our flexible itinerary allows you …More

Likely to Sell Out
Likely to Sell Out

Embark on a truly unique journey, where your experience is shaped by your desires. Perfect for families, couples, or groups, our flexible itinerary allows you...

7 hours
5.0 (71)
from
$1,830
Private Day Charter Classic Sailboat

To maximize your day and our destination options in the National Park, we offer flexible timing allowing for an easy transfer away from the busy …More

To maximize your day and our destination options in the National Park, we offer flexible timing allowing for an easy transfer away from the busy...

4 to 5 hours Hotel pickup offered Free Cancellation
5.0 (70)
from
$1,395
Private Luxury Catamaran - Saona or Catalina island

This private day is yours to tailor! Hand pick off track spots and activities for a full personal experience that the crew will help you …More

This private day is yours to tailor! Hand pick off track spots and activities for a full personal experience that the crew will help you...

4 to 8 hours Hotel pickup offered Free Cancellation
5.0 (69)
from
$1,990
Montego Bay Private Yacht Tour with Open Bar and Lunch

We are not just offering a cruise. We are offering an escape and tranquility. Our aim is to provide sophistication, outstanding customer service and the …More

Montego Bay, Jamaica

We are not just offering a cruise. We are offering an escape and tranquility. Our aim is to provide sophistication, outstanding customer service and the...

4 hours Free Cancellation
4.9 (68)
from
$2,500
Aquaspace Sunset Sail and Snorkel Tour on Bonaire with Diner

This boat is one of a kind, specially designed for underwater research and once part of Jacques Cousteau's legendary fleet. It features an air-conditioned underwater …More

Kralendijk, Bonaire

This boat is one of a kind, specially designed for underwater research and once part of Jacques Cousteau's legendary fleet. It features an air-conditioned underwater...

4 hours Free Cancellation
5.0 (67)
from
$135
Sailing lagoon day: slide between mangrove & reefs

Morning boarding in a calm sea, with a simple welcome over coffee. From the first edges, sailing sets the pace. The lagoon, protected by the …More

Likely to Sell Out
Likely to Sell Out
Basse-Terre Island, Guadeloupe

Morning boarding in a calm sea, with a simple welcome over coffee. From the first edges, sailing sets the pace. The lagoon, protected by the...

8 to 9 hours Free Cancellation
5.0 (62)
from
$94
Private Snorkeling in Punta Cana

This excursion will allow you to enjoy the ocean on your own terms. You will be able to snorkel, drink, dance, swim, enjoy the lovely …More

Punta Cana, Dominican Republic

This excursion will allow you to enjoy the ocean on your own terms. You will be able to snorkel, drink, dance, swim, enjoy the lovely...

3 hours Hotel pickup offered Free Cancellation
5.0 (62)
from
$920
Sailing Discovery Day Tour in Martinique

Live a day dream on a legendary sailing boat, a trimaran. Discover the wonderland coasts of one of the most beautiful Caribbean island.  • From …More

Live a day dream on a legendary sailing boat, a trimaran. Discover the wonderland coasts of one of the most beautiful Caribbean island.  • From...

7 hours 45 minutes Free Cancellation
4.9 (62)
from
$126
St. Thomas Maho Bay Turtle Snorkel Sail - Ritz-Carlton

Sail away aboard Lady Lynsey II into the Virgin Island’s National Park to discover the wonders of snorkeling with sea turtles. …More

Sail away aboard Lady Lynsey II into the Virgin Island’s National Park to discover the wonders of snorkeling with sea turtles....

5 hours Free Cancellation
4.9 (61)
from
$159
Adults Only Jolly Pirate Sunset Grub and Grog Dinner Sail

Join the Jolly Crew aboard Aruba's liveliest sunset party cruise with an opportunity to swing from the Jolly Pirate yard arm. There's a DJ aboard …More

Join the Jolly Crew aboard Aruba's liveliest sunset party cruise with an opportunity to swing from the Jolly Pirate yard arm. There's a DJ aboard...

3 hours
4.9 (61)
from
$125
Catamaran Sunset Sail

You are on course for a good time with Bermuda's original sunset Sail. Soak up the setting sun and sensual seascapes as we sail in …More

Likely to Sell Out
Likely to Sell Out

You are on course for a good time with Bermuda's original sunset Sail. Soak up the setting sun and sensual seascapes as we sail in...

1 hour 30 minutes Free Cancellation
4.8 (59)
from
$94
Luxury Catamaran Private Charter in St. Maarten/St. Martin

Get the mega yacht experience aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a custom-made sailing catamaran appointed with all the …More

Get the mega yacht experience aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a custom-made sailing catamaran appointed with all the...

7 hours 30 minutes Free Cancellation
5.0 (52)
from
$330
Barbados Snorkeling and Sailing Adventure for Small Groups

Our team knows how to blend adventure and relaxation perfectly. From snorkeling with sea turtles and exploring shipwrecks to sipping rum punch as you sail …More

Likely to Sell Out
Likely to Sell Out

Our team knows how to blend adventure and relaxation perfectly. From snorkeling with sea turtles and exploring shipwrecks to sipping rum punch as you sail...

3 hours Hotel pickup offered Free Cancellation
4.8 (51)
from
$85
Hands on Sailing Tour in Rodney Bay St Lucia

Enjoy an exciting and adrenaline filled sail around Rodney Bay or further afield, learning the skills and techniques of sailing a race yacht. As you …More

Likely to Sell Out
Likely to Sell Out

Enjoy an exciting and adrenaline filled sail around Rodney Bay or further afield, learning the skills and techniques of sailing a race yacht. As you...

3 hours Free Cancellation
4.9 (51)
from
$150
San Juan Bay Private Tour with Drinks and Tapas: 4+ people

Get more time, See more do more!, More Space! Welcome aboard your private water tour aboard a choice between a 37 foot sailboat ot a …More

Get more time, See more do more!, More Space! Welcome aboard your private water tour aboard a choice between a 37 foot sailboat ot a...

3 hours Free Cancellation
5.0 (51)
from
$166
St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton

This one of a kind excursion to Jost Van Dyke allows passengers to spend the most time on the island out of all other group …More

This one of a kind excursion to Jost Van Dyke allows passengers to spend the most time on the island out of all other group...

8 hours Free Cancellation
4.9 (50)
from
$309
THE BEST Sunshine PARTY BOAT CATAMARAN IN DOMINICAN REPUBLIC

A catamaran or boat equipped for parties, with music, an open bar, and dancing. Water Activities: Snorkeling in coral reefs, visiting natural pools, and enjoying …More

Punta Cana, Dominican Republic

A catamaran or boat equipped for parties, with music, an open bar, and dancing. Water Activities: Snorkeling in coral reefs, visiting natural pools, and enjoying...

3 hours 30 minutes Hotel pickup offered
5.0 (50)
from
$69
Full-Day Sailing Tour in Virgin Islands National Park

Set sail and explore the Virgin Islands National Park! Enjoy a day of sailing and snorkeling with lunch and drinks provided! Where to meet: We …More

Likely to Sell Out
Likely to Sell Out

Set sail and explore the Virgin Islands National Park! Enjoy a day of sailing and snorkeling with lunch and drinks provided! Where to meet: We...

6 hours Free Cancellation
4.9 (49)
from
$285
Good Vibration Catamaran Sail Swim Snorkel

Hop aboard Bermuda's newest catamaran, good vibrations, for a fun-filled excursion of cruising, sailing, swimming, lounging and snorkeling along the shoreline. …More

Likely to Sell Out
Likely to Sell Out

Hop aboard Bermuda's newest catamaran, good vibrations, for a fun-filled excursion of cruising, sailing, swimming, lounging and snorkeling along the shoreline....

3 hours Free Cancellation
4.8 (48)
from
$111

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