Top Caribbean Sailing Trips

Q: Which Caribbean Sailing Trips have Instant Confirmation?

Caribbean Sailing Trips with Instant Confirmation include: San Juan: Snorkeling with Turtles and Complimentary Videos St. Martin Sunset Sail Half Day Party Boat and Snorkeling in Punta Cana Punta Cana Party Booze Cruise, open bar, snorkeling Only Adult Beach Buggy Excursion in Punta Cana Bavaro View all Tours with Instant Confirmation →

Q: I need a ride! Which Caribbean Sailing Trips have Hotel Pickup?

No problem. These Caribbean Sailing Trips include Hotel Pickup: Half Day Party Boat and Snorkeling in Punta Cana Punta Cana Party Booze Cruise, open bar, snorkeling Only Adult Beach Buggy Excursion in Punta Cana Bavaro Parasailing in Bavaro Full Day Excursion to Isla Saona from Punta Cana View all Tours with Hotel Pickup →

Q: Got any more Caribbean trip ideas?

We sure do. Check out our curated lists of hand-picked Caribbean Tours. Top 10 Caribbean 2026 Senior-friendly tours Caribbean The best tours and activities for culture lovers in Caribbean Top Day Trips from Caribbean Things to do in Caribbean this summer View all Caribbean Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Caribbean?

Based on our sales data over the past year, the most popular styles of tours and activities in Caribbean are: Caribbean Luxury & Special Occasions Caribbean Luxury Tours Caribbean Tours & Sightseeing Caribbean Shore Excursions Caribbean Port Transfers View all tour styles in Caribbean →

Deluxe Half-Day Snorkel Sail on Luxury Catamaran

Set sail aboard the luxury sailing catamaran Lady Grace to explore the Turks & Caicos Barrier Reef, home to some of the best snorkeling in …More

4.9 (445)

Deluxe Half-Day Snorkel Sail on Luxury Catamaran

Set sail aboard the luxury sailing catamaran Lady Grace to explore the Turks & Caicos Barrier Reef, home to some of the best snorkeling in...

4 hours 30 minutes Free Cancellation

4.9 (445)

from
$159

Sail/Snorkel Adventure from Sapphire Marina,STT NO CROWDS~ 6 GUEST MAX

We offer a semi private setting with a maximum of 6 guest and a personalized experience. The sailboat Cosmos Mariner is stable, sea kindly, and …More

5.0 (257)

Sail/Snorkel Adventure from Sapphire Marina,STT NO CROWDS~ 6 GUEST MAX

We offer a semi private setting with a maximum of 6 guest and a personalized experience. The sailboat Cosmos Mariner is stable, sea kindly, and...

3 hours Free Cancellation

5.0 (257)

from
$159

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

4.9 (61)

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....

5 hours Free Cancellation

4.9 (61)

from
$159

Half Day Private Sailing Catamaran and Snorkel Trip to St John

Sail with Liberty guests experience real sailing on our spacious, private catamaran. We sail you to the St John National Park for spectacular snorkeling and …More

5.0 (127)

Half Day Private Sailing Catamaran and Snorkel Trip to St John

Sail with Liberty guests experience real sailing on our spacious, private catamaran. We sail you to the St John National Park for spectacular snorkeling and...

3 hours 30 minutes Free Cancellation

5.0 (127)

from
$165

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

5.0 (51)

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...

3 hours Free Cancellation

5.0 (51)

from
$166

Saona Island small group and relax - luxury catamaran

Choosing the Quetzal is choosing the difference and the quality of service! Quetzal boat is the only fully equipped 75-foot boat Small Group: allowing everyone …More

La Romana, Dominican Republic

4.9 (378)

Saona Island small group and relax - luxury catamaran

Choosing the Quetzal is choosing the difference and the quality of service! Quetzal boat is the only fully equipped 75-foot boat Small Group: allowing everyone...

8 hours Hotel pickup offered Free Cancellation

4.9 (378)

from
$169

Hakuna Matata - St Maarten Catamaran day cruise

Enjoy a relaxed day perfect for families (kids welcome!), couples, and groups. Captain Robert, with years of experience sailing the world’s oceans, shares captivating stories …More

5.0 (160)

Hakuna Matata - St Maarten Catamaran day cruise

Enjoy a relaxed day perfect for families (kids welcome!), couples, and groups. Captain Robert, with years of experience sailing the world’s oceans, shares captivating stories...

7 hours

5.0 (160)

from
$169

Luxury Catamaran Cruise: Sip, Sail, Snorkel, and Swim with Pigs!

Dive into a world of difference with Tropical Breeze as we redefine the classic Bahamian cruise experience. Here's what sets us apart as the ultimate …More

5.0 (88)

Luxury Catamaran Cruise: Sip, Sail, Snorkel, and Swim with Pigs!

Dive into a world of difference with Tropical Breeze as we redefine the classic Bahamian cruise experience. Here's what sets us apart as the ultimate...

6 hours Free Cancellation

5.0 (88)

from
$179

Full-Day Sailing and Snorkeling Excursion to Les Saintes

Embark on a unique adventure that combines sailing and snorkeling in one of Guadeloupe’s must-see destinations: the archipelago of Les Saintes. With a small group …More

Basse-Terre Island, Guadeloupe

5.0 (108)

Full-Day Sailing and Snorkeling Excursion to Les Saintes

Embark on a unique adventure that combines sailing and snorkeling in one of Guadeloupe’s must-see destinations: the archipelago of Les Saintes. With a small group...

9 hours Free Cancellation

5.0 (108)

from
$183

Private Luxury Sailing from Casa de Campo to Catalina Island

Set sail on an unforgettable day adventure from the exclusive Marina Casa de Campo, a luxury destination in La Romana. With a max capacity of …More

Punta Cana, Dominican Republic

5.0 (7)

Private Luxury Sailing from Casa de Campo to Catalina Island

Set sail on an unforgettable day adventure from the exclusive Marina Casa de Campo, a luxury destination in La Romana. With a max capacity of...

6 hours 15 minutes Hotel pickup offered Free Cancellation

5.0 (7)

from
$188

Create unforgettable memories on a completely private Sunset & Champagne Cruise aboard our elegant 48-ft sailing yacht Galaxie, reserved exclusively for your group. No mixed …More

5.0 (5)

Private Luxury Sunset Cruise Curaçao

Create unforgettable memories on a completely private Sunset & Champagne Cruise aboard our elegant 48-ft sailing yacht Galaxie, reserved exclusively for your group. No mixed...

2 hours Free Cancellation

5.0 (5)

from
$190

Zip-lining/Horseback Rides/Cat & Atv Inclusive Act with Transpo From Montego Bay

This is a private customizable day tour which Highlights the beauty of the western part of the island. This Tour is a complete package of …More

Montego Bay, Jamaica

5.0 (21)

Zip-lining/Horseback Rides/Cat & Atv Inclusive Act with Transpo From Montego Bay

This is a private customizable day tour which Highlights the beauty of the western part of the island. This Tour is a complete package of...

5 hours Hotel pickup offered Free Cancellation

5.0 (21)

from
$190

Mojito - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Mojito, one of our luxury sailing catamarans, for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private …More

5.0 (1)

Mojito - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Mojito, one of our luxury sailing catamarans, for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private...

4 hours Free Cancellation

5.0 (1)

from
$190

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

4.8 (24)

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...

8 hours Free Cancellation

4.8 (24)

from
$192

Be Happy - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Be Happy for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private sailing experience with your group, …More

5.0 (10)

Be Happy - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Be Happy for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private sailing experience with your group,...

4 hours Free Cancellation

5.0 (10)

from
$195

ALL INCLUSIVE Full Day snorkeling & sunset cruise with boat dogs

Sail to the world-famous Underwater Sculpture Park and enjoy a fully guided snorkeling tour of each of the sculptures. Enjoy a freshly prepared and delicious …More

4.9 (77)

ALL INCLUSIVE Full Day snorkeling & sunset cruise with boat dogs

Sail to the world-famous Underwater Sculpture Park and enjoy a fully guided snorkeling tour of each of the sculptures. Enjoy a freshly prepared and delicious...

8 hours Free Cancellation

4.9 (77)

from
$209

Don't Worry - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Don't Worry, one of our luxury sailing catamarans, for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a …More

5.0 (5)

Don't Worry - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Don't Worry, one of our luxury sailing catamarans, for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a...

4 hours Free Cancellation

5.0 (5)

from
$210

Norman Island - The Indians & The Caves Sailing & Snorkel Tour

Welcome aboard, fellow adventurers, to the breathtaking paradise of the BVI! Here, amidst crystal-clear waters and gentle sea breezes, lies a world of wonder waiting …More

5.0 (77)

Norman Island - The Indians & The Caves Sailing & Snorkel Tour

Welcome aboard, fellow adventurers, to the breathtaking paradise of the BVI! Here, amidst crystal-clear waters and gentle sea breezes, lies a world of wonder waiting...

6 hours Free Cancellation

5.0 (77)

from
$225

Curaçao Private Morning Snorkeling Boat Tour

Create unforgettable memories with this exclusive private sailing experience in Curaçao. Our elegant 48-ft sailing yacht Galaxie is reserved entirely for your group, allowing you …More

5.0 (4)

Curaçao Private Morning Snorkeling Boat Tour

Create unforgettable memories with this exclusive private sailing experience in Curaçao. Our elegant 48-ft sailing yacht Galaxie is reserved entirely for your group, allowing you...

3 hours Free Cancellation

5.0 (4)

from
$225

Private Sunset Serenade Begin your exclusive 2-hour journey with a warm welcome at our secluded pier, complete with refreshing cold towels and personalised attention. Voyage …More

Sunset Deluxe 2-Hour Private Charter in Montego Bay, Open Bar

Private Sunset Serenade Begin your exclusive 2-hour journey with a warm welcome at our secluded pier, complete with refreshing cold towels and personalised attention. Voyage...

2 hours Free Cancellation

from
$227