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Top Caribbean Sailing Trips

262 Results
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 1/2 Day Yacht Charter in Bonaire - Customizable!

100% Customizable! Our private charter experience on Bonaire is unmatched. As the only American yacht operators on the island, we understand the importance of personalized …More

100% Customizable! Our private charter experience on Bonaire is unmatched. As the only American yacht operators on the island, we understand the importance of personalized...

4 hours 30 minutes
5.0 (46)
from
$2,299
Private Caribbean Snorkeling Cruise At Punta Cana & Sharks, Stingray Encounter

Perfect for both small and large groups. Explore the beauty of Punta Cana's white sands and turquoise blue clear waters in your own upgraded private …More

Perfect for both small and large groups. Explore the beauty of Punta Cana's white sands and turquoise blue clear waters in your own upgraded private...

4 hours Hotel pickup offered Free Cancellation
5.0 (45)
from
$1,295
The Soul Of Pirates Boat Trip Adventure Caribbean Charter Morning / Sunset SXM

A timeless adventure aboard our sailboat. Come live an unforgettable experience on a sailboat. No engine, sail like pirates. Possibility to hold the helm with …More

A timeless adventure aboard our sailboat. Come live an unforgettable experience on a sailboat. No engine, sail like pirates. Possibility to hold the helm with...

4 hours Free Cancellation
5.0 (44)
from
$124
Beach Trip Along The West Coast Of Curacao

Sailing along Curacao’s West Coast on the biggest catamaran of Curacao is a must do attraction! The trip starts at 08:30 am. As soon as …More

Sailing along Curacao’s West Coast on the biggest catamaran of Curacao is a must do attraction! The trip starts at 08:30 am. As soon as...

8 hours Free Cancellation
4.9 (44)
from
$140
Half Day Snorkeling Trip in Grenada

Come enjoy a relaxing Halfday snorkeling trip with us as we cruise along the west coast of Grenada to make our way to the iconic …More

Come enjoy a relaxing Halfday snorkeling trip with us as we cruise along the west coast of Grenada to make our way to the iconic...

4 hours Free Cancellation
5.0 (44)
from
$85
Snorkel Lunch & Lounge: Bluewater or Snorkel and Lunch: Leeward

Scenic Cruise: The experience begins with a relaxing catamaran cruise, taking you along the picturesque coastline of Frigate Bay into the Southeast Peninsula at Shitten's …More

Likely to Sell Out
Likely to Sell Out

Scenic Cruise: The experience begins with a relaxing catamaran cruise, taking you along the picturesque coastline of Frigate Bay into the Southeast Peninsula at Shitten's...

4 hours Hotel pickup offered Free Cancellation
4.9 (41)
from
$125
Luxury Private Sunset Cruise for up to 6 guests

An Unforgettable Sailing Experience, Just for You. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us …More

Likely to Sell Out
Likely to Sell Out

An Unforgettable Sailing Experience, Just for You. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us...

2 hours Free Cancellation
5.0 (38)
from
$695
Small Group: Snorkeling Cruise Adventure around the Punta Cana Coast

SINGLES, COUPLES & GROUPS can all explore the beautiful coast of Punta Cana on this safe route. Embark on a party in one of the …More

Punta Cana, Dominican Republic

SINGLES, COUPLES & GROUPS can all explore the beautiful coast of Punta Cana on this safe route. Embark on a party in one of the...

3 hours 30 minutes Hotel pickup offered Free Cancellation
4.9 (38)
from
$60
Private, All Inclusive, Double-Decker Catamaran in Punta Cana

Our Catamaran Party Boat Tour is a MUST when it comes to Punta Cana experiences. This booze cruise takes you along the Coast of Bavaro …More

Punta Cana, Dominican Republic

Our Catamaran Party Boat Tour is a MUST when it comes to Punta Cana experiences. This booze cruise takes you along the Coast of Bavaro...

3 hours Hotel pickup offered Free Cancellation
5.0 (37)
from
$83
Private Luxury Sailing Experience Curacao

The experience balances scenic cruising, relaxing time at anchor and a peaceful sail back with the sails raised when weather conditions allow. As owners and …More

Likely to Sell Out
Likely to Sell Out

The experience balances scenic cruising, relaxing time at anchor and a peaceful sail back with the sails raised when weather conditions allow. As owners and...

4 hours Free Cancellation
5.0 (36)
from
$260
Leisure Full Day Catamaran (Blue, Aqua or LIC)

Crafted Catamarans: Specifically designed for water tours, comfort, spacious decks, shaded seating areas, bar, and restroom for the enjoyment of passengers. Scenic Coastal Routes: Allowing …More

Likely to Sell Out
Likely to Sell Out

Crafted Catamarans: Specifically designed for water tours, comfort, spacious decks, shaded seating areas, bar, and restroom for the enjoyment of passengers. Scenic Coastal Routes: Allowing...

7 hours Hotel pickup offered Free Cancellation
5.0 (32)
from
$155
Group Sunset Sail St. John

We are a family owned small business; we have a love for true sailing and authentic relationships here in the islands. Looking for more time …More

We are a family owned small business; we have a love for true sailing and authentic relationships here in the islands. Looking for more time...

2 hours 30 minutes Free Cancellation
5.0 (32)
from
$245
Stroll and Initiation to Sailing in the Baie des Saintes

I invite you to come and share my passion for sailing and navigation in one of the most beautiful bays in the world! I am …More

I invite you to come and share my passion for sailing and navigation in one of the most beautiful bays in the world! I am...

3 hours Free Cancellation
5.0 (31)
from
$86
Private catamaran sail & snorkel cruise

We are a boutique catamaran specializing in private trips for families and small groups looking for a special day on vacation, We avoid the crowds …More

Likely to Sell Out
Likely to Sell Out

We are a boutique catamaran specializing in private trips for families and small groups looking for a special day on vacation, We avoid the crowds...

3 hours Free Cancellation
5.0 (30)
from
$500
Sail, Shop and Snorkel in St. John from Westin Frenchman's Reef

Experience the best of two tropical islands! Sail to the island escape of St. John from St. Thomas aboard the beautiful Flying Frenchman. After snorkeling …More

Experience the best of two tropical islands! Sail to the island escape of St. John from St. Thomas aboard the beautiful Flying Frenchman. After snorkeling...

7 hours Free Cancellation
4.8 (29)
from
$129
Curacao: Private Luxury Boat Tour Half Day

Create unforgettable memories with Maxie Sailing! We specialize in private luxury sailing experiences in Curacao, with our spacious 48-ft yacht reserved exclusively for you and …More

Likely to Sell Out
Likely to Sell Out

Create unforgettable memories with Maxie Sailing! We specialize in private luxury sailing experiences in Curacao, with our spacious 48-ft yacht reserved exclusively for you and...

4 hours Free Cancellation
5.0 (25)
from
$260
Parasailing in Bavaro

This is Punta Cana like you’ve never imagined. Parasailing is a thrilling activity that’ll have you whooping over the Caribbean. After pick-up, head to Corales …More

Punta Cana, Dominican Republic

This is Punta Cana like you’ve never imagined. Parasailing is a thrilling activity that’ll have you whooping over the Caribbean. After pick-up, head to Corales...

2 hours Hotel pickup offered Free Cancellation
4.8 (25)
from
$57
The Soul Of Pirates Boat Trip Adventure Caribbean Charter Full Day SXM

Set off from Saint-Martin for a full day on a wind-powered boat, without an engine. With the captain's help, take the helm and help hoist …More

Set off from Saint-Martin for a full day on a wind-powered boat, without an engine. With the captain's help, take the helm and help hoist...

8 hours Free Cancellation
4.8 (24)
from
$192
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

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