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Top Caribbean Sailing Trips

262 Results
Iconic Aruba Sail and Snorkel Experience

Experience the joy of sailing along Aruba’s stunning beaches on a spacious catamaran & snorkeling at the marine sanctuary, Catalina bay, and the famous Antilla shipwreck. …More

Experience the joy of sailing along Aruba’s stunning beaches on a spacious catamaran & snorkeling at the marine sanctuary, Catalina bay, and the famous Antilla shipwreck....

2 hours 30 minutes Free Cancellation
4.8 (510)
from
$67
Dolphin Catamaran Snorkel and Sail with Open Bar

Enjoy a delightful 3-hour adventure featuring two captivating snorkeling stops. First, explore the iconic shipwreck "Antilla", a fascinating relic resting beneath the azure waters, brimming …More

Enjoy a delightful 3-hour adventure featuring two captivating snorkeling stops. First, explore the iconic shipwreck "Antilla", a fascinating relic resting beneath the azure waters, brimming...

3 hours Free Cancellation
4.8 (2,798)
from
$69
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
Experience a Submarine Scooter with ScubaDoo Punta Cana

ScubaDoo Punta Cana is a diving and snorkeling adventure that takes you to some of the most beautiful and unspoiled areas in the Caribbean Sea …More

ScubaDoo Punta Cana is a diving and snorkeling adventure that takes you to some of the most beautiful and unspoiled areas in the Caribbean Sea...

5 hours Hotel pickup offered Free Cancellation
4.1 (13)
from
$69
Party Boat Cruise & Open Bar with Snorkeling in Punta Cana

Our animation team and captain are highly trained for this type of events with a lot of experience in this type of adventures, fun professionals …More

Punta Cana, Dominican Republic

Our animation team and captain are highly trained for this type of events with a lot of experience in this type of adventures, fun professionals...

4 hours Hotel pickup offered Free Cancellation
3.0 (1)
from
$69
Party Boat - Booze Cruise Punta Cana

If you are looking for parties at sunrise or sunset on a boat where alcohol flows freely and the music pumped, then climb aboard the …More

Punta Cana, Dominican Republic

If you are looking for parties at sunrise or sunset on a boat where alcohol flows freely and the music pumped, then climb aboard the...

4 hours Hotel pickup offered Free Cancellation
1.7 (3)
from
$70
Che’s snorkel catamaran! turtles, wrecks & pickup (small group)

(Semi private) We are the only cruise that sails early to avoid the crowds of commercial tours. That’s our niche! Che’s snorkel focused trip has …More

(Semi private) We are the only cruise that sails early to avoid the crowds of commercial tours. That’s our niche! Che’s snorkel focused trip has...

3 hours Hotel pickup offered Free Cancellation
5.0 (570)
from
$70
San Juan: VIP Snorkeling with Turtles Tour

Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginner-friendly adventure led by a professional guide in …More

Likely to Sell Out
Likely to Sell Out

Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginner-friendly adventure led by a professional guide in...

1 hour 30 minutes Free Cancellation
5.0 (329)
from
$70
Aruba Sunset Sail Experience

Unwind and end your day on a high note with this relaxing cruise. Climb aboard a comfortable open-deck catamaran and set sail to admire Aruba's …More

Unwind and end your day on a high note with this relaxing cruise. Climb aboard a comfortable open-deck catamaran and set sail to admire Aruba's...

2 hours Free Cancellation
4.7 (641)
from
$73
Punta Cana: Catamaran Tour, Reef Snorkeling and Unlimited Drinks!

Embark on a thrilling catamaran ride, where you can relax and enjoy the stunning Caribbean views. Sip on refreshing drinks as you cruise along the …More

Punta Cana, Dominican Republic

Embark on a thrilling catamaran ride, where you can relax and enjoy the stunning Caribbean views. Sip on refreshing drinks as you cruise along the...

3 hours Hotel pickup offered Free Cancellation
4.9 (174)
from
$74
Saona Island Tour and Catamaran Party from Punta Cana

Saona Island is like a paradise on earth surrounded by white sand beaches, crystal clear turquoise waters and countless palm trees, this environment invites you …More

Punta Cana, Dominican Republic

Saona Island is like a paradise on earth surrounded by white sand beaches, crystal clear turquoise waters and countless palm trees, this environment invites you...

9 hours Hotel pickup offered Free Cancellation
4.6 (28)
from
$74
Live Music Sunset Sail

Rated the number 1 Sunset Sail on St Croix! Magical. Unforgettable. The best way to enjoy a sunset on St. Croix. This is how our …More

Rated the number 1 Sunset Sail on St Croix! Magical. Unforgettable. The best way to enjoy a sunset on St. Croix. This is how our...

2 hours 30 minutes Free Cancellation
4.9 (397)
from
$75
Salsa, Sunsets & Mojitos at Sea

Get a sense of Havana, Cuba, as you sip a mojito while sailing on an open-deck catamaran in Aruba. Watch the setting sun and learn …More

Get a sense of Havana, Cuba, as you sip a mojito while sailing on an open-deck catamaran in Aruba. Watch the setting sun and learn...

2 hours Free Cancellation
4.9 (47)
from
$75
Private Sailing Tour of Pirate Waters and Shipwrecks

Salt River Bay, St. Croix, was a pirate nest for two and a half centuries, used by Kalinago, Conquistadors, Buccaneers, and Pirates, and appears almost …More

Salt River Bay, St. Croix, was a pirate nest for two and a half centuries, used by Kalinago, Conquistadors, Buccaneers, and Pirates, and appears almost...

2 hours Free Cancellation
4.9 (24)
from
$75
Catamaran Sunset Cruise with open bar and bites

Our most relaxing trip in our list. Unwind with a drink and some snacks while the sun sets. Step aboard the sailing catamaran and cruise …More

Our most relaxing trip in our list. Unwind with a drink and some snacks while the sun sets. Step aboard the sailing catamaran and cruise...

2 hours 30 minutes Free Cancellation
4.8 (171)
from
$79
Isla Saona from Punta Cana: Catamaran and Boat Tour

Live the Magic of Saône Island! Ready to discover paradise? Just a few minutes by boat from La Romana beach ☀️ Beaches of Dream White …More

Punta Cana, Dominican Republic

Live the Magic of Saône Island! Ready to discover paradise? Just a few minutes by boat from La Romana beach ☀️ Beaches of Dream White...

8 hours Hotel pickup offered Free Cancellation
4.8 (18)
from
$79
Excursion to Catalina Island and Snorkeling from Punta Cana

Experience an unforgettable adventure on a snorkeling tour with lunch and guide. Relax with access to an open bar and arrive to equipment ready and …More

Punta Cana, Dominican Republic

Experience an unforgettable adventure on a snorkeling tour with lunch and guide. Relax with access to an open bar and arrive to equipment ready and...

8 hours Hotel pickup offered Free Cancellation
4.2 (35)
from
$79
Nassau Sail and Snorkel with Open Tropical Bar

Enjoy snorkeling, sailing, and sunning aboard a custom-built catamaran. We will sail out to one of the Islands most beautiful reefs teeming with tropical fish …More

Likely to Sell Out
Likely to Sell Out

Enjoy snorkeling, sailing, and sunning aboard a custom-built catamaran. We will sail out to one of the Islands most beautiful reefs teeming with tropical fish...

3 hours 30 minutes Free Cancellation
4.5 (102)
from
$80
Bioluminescent Lagoon Tour: Night Swimming and Liming in Jamaica

This is one of the many wonders of the world. A beautiful night swim activity that all travelers to Jamaica must experience at-lease once. …More

Montego Bay, Jamaica

This is one of the many wonders of the world. A beautiful night swim activity that all travelers to Jamaica must experience at-lease once....

1 hour 30 minutes Hotel pickup offered Free Cancellation
4.6 (58)
from
$80
Sunset Bliss Catamaran Tour

Enjoy smooth sunset sailing on one of our catamarans along the coast of Bonaire. Let us get you spoiled with luxury snacks, drinks and chill …More

Enjoy smooth sunset sailing on one of our catamarans along the coast of Bonaire. Let us get you spoiled with luxury snacks, drinks and chill...

2 hours 30 minutes
5.0 (16)
from
$80

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