Top Caribbean Sailing Trips

Q: What are the best options for Caribbean Sailing Trips?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Caribbean Sailing Trips are: Aruba Snorkel Cruise with Open Bar and Lunch Catamaran Sunset Sail Private Catamaran wonderful Snorqueling slide & entartaiment team Barbados Snorkeling and Sailing Adventure for Small Groups Aruba Sunset Sail Dinner Cruise with Open Bar by Catamaran

Q: What are the best kid-friendly options for Caribbean Sailing Trips Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Caribbean Sailing Trips are: St. Martin Sunset Sail Half Day Party Boat and Snorkeling in Punta Cana Parasailing in Bavaro Full Day Excursion to Isla Saona from Punta Cana Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran View all kid-friendly Tours →

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 →

Coral Quest: A Marine Conservation Experience (All Ages)

Discover the Caribbean Beneath the Surface. Coral Quest is more than a catamaran tour, it's an unforgettable marine conservation adventure for families and ocean lovers …More

Punta Cana, Dominican Republic

5.0 (569)

Coral Quest: A Marine Conservation Experience (All Ages)

Discover the Caribbean Beneath the Surface. Coral Quest is more than a catamaran tour, it's an unforgettable marine conservation adventure for families and ocean lovers...

4 hours Hotel pickup offered Free Cancellation

5.0 (569)

from
$114

Enjoy the majestic views as you travel down the southern coast of the island. A stop will be made at Cades Reef for the opportunity to snorkel …More

4.5 (74)

Sail and Snorkel at Cades Reef

Enjoy the majestic views as you travel down the southern coast of the island. A stop will be made at Cades Reef for the opportunity to snorkel...

6 hours Free Cancellation

4.5 (74)

from
$115

Saona by Speedboat: Private Beach & Snorkeling – Small Group

Enjoy Saona Island away from the crowds on a private beach reserved just for your small group. Snorkel in turquoise waters, relax under palm trees, …More

La Romana, Dominican Republic

5.0 (2)

Saona by Speedboat: Private Beach & Snorkeling – Small Group

Enjoy Saona Island away from the crowds on a private beach reserved just for your small group. Snorkel in turquoise waters, relax under palm trees,...

7 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (2)

from
$115

San Juan Catamaran Sunset Sail with Drinks Included

Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset lighting. This 2-hour sail aboard a 37ft catamaran …More

5.0 (672)

San Juan Catamaran Sunset Sail with Drinks Included

Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset lighting. This 2-hour sail aboard a 37ft catamaran...

2 hours Free Cancellation

5.0 (672)

from
$119

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

Come swim with the resident green sea turtles and tropical fish on this 3 hour snorkel & sail adventure in St. Thomas aboard The VI …More

4.8 (2,279)

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

Come swim with the resident green sea turtles and tropical fish on this 3 hour snorkel & sail adventure in St. Thomas aboard The VI...

3 hours Free Cancellation

4.8 (2,279)

from
$119

Historical San Juan Bay Sunset Sailing Tour

Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind, the peace from no engine noise, no …More

4.7 (725)

Historical San Juan Bay Sunset Sailing Tour

Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind, the peace from no engine noise, no...

2 hours Free Cancellation

4.7 (725)

from
$119

Snorkel with Turtles at WW2 Shipwreck Includes Sunset & BBQ

Step aboard on one of the famous Spronk designs Catamarans and enjoy the longest sailing tour on the island 4.5 unforgettable hours on the Caribbean …More

Palm - Eagle Beach, Aruba

4.7 (365)

Snorkel with Turtles at WW2 Shipwreck Includes Sunset & BBQ

Step aboard on one of the famous Spronk designs Catamarans and enjoy the longest sailing tour on the island 4.5 unforgettable hours on the Caribbean...

4 hours 30 minutes Hotel pickup offered Free Cancellation

4.7 (365)

from
$119

Aruba Sail and Snorkel with Turtles at WW2 Shipwreck Includes BBQ

Our catamaran accommodates up to 50 passengers, but we limit each cruise to fewer than 35 guests for maximum comfort. …More

Palm - Eagle Beach, Aruba

4.8 (153)

Aruba Sail and Snorkel with Turtles at WW2 Shipwreck Includes BBQ

Our catamaran accommodates up to 50 passengers, but we limit each cruise to fewer than 35 guests for maximum comfort....

4 hours 30 minutes Free Cancellation

4.8 (153)

from
$119

Samaná + Raised Key + Horse Tour from Punta Cana

Visit Cayo Levantado (Bacardi Island) and El Limón Falls. Enjoy a true experience of the Eastern Coastal Plain of the Dominican Republic, traveling from different …More

Punta Cana, Dominican Republic

5.0 (5)

Samaná + Raised Key + Horse Tour from Punta Cana

Visit Cayo Levantado (Bacardi Island) and El Limón Falls. Enjoy a true experience of the Eastern Coastal Plain of the Dominican Republic, traveling from different...

8 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$119

Catamaran Snorkel & BBQ Sail (cruise friendly)

The only catamaran tour that includes guided snorkeling and on board lunch prepared on the grill! Our schedule is perfectly attuned to arrival and departure …More

4.9 (205)

Catamaran Snorkel & BBQ Sail (cruise friendly)

The only catamaran tour that includes guided snorkeling and on board lunch prepared on the grill! Our schedule is perfectly attuned to arrival and departure...

4 hours

4.9 (205)

from
$120

4 Hours Party Boat Catamaran Cruise in Negril

Book our unique Catamaran experience. You will be picked up at your hotel. You will be travelling in a comfortable fully air conditioned vehicle from …More

Montego Bay, Jamaica

5.0 (11)

4 Hours Party Boat Catamaran Cruise in Negril

Book our unique Catamaran experience. You will be picked up at your hotel. You will be travelling in a comfortable fully air conditioned vehicle from...

4 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$120

2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)

There’s no better way to see the setting Caribbean sun than with a Champagne Sail in Turks and Caicos. Sail past the white sand beaches …More

4.9 (1,137)

2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)

There’s no better way to see the setting Caribbean sun than with a Champagne Sail in Turks and Caicos. Sail past the white sand beaches...

2 hours Hotel pickup offered Free Cancellation

4.9 (1,137)

from
$122

Spend a relaxing evening in Aruba on a sunset cruise followed by a waterfront seafood dinner. Sail along Aruba’s west coast, enjoying snacks and an …More

4.5 (1,020)

Aruba Sunset Cruise plus Seaside Dinner

Spend a relaxing evening in Aruba on a sunset cruise followed by a waterfront seafood dinner. Sail along Aruba’s west coast, enjoying snacks and an...

3 hours Free Cancellation

4.5 (1,020)

from
$122

Sailing has sensation. Come live an unforgettable experience on a sailboat. A timeless adventure aboard our sailboat. Come hoist the sails on the Caribbean Sea …More

5.0 (11)

Half-Day Sailing Boat Adventure

Sailing has sensation. Come live an unforgettable experience on a sailboat. A timeless adventure aboard our sailboat. Come hoist the sails on the Caribbean Sea...

4 hours Free Cancellation

5.0 (11)

from
$123

Take a relaxing cruise along the picturesque shores of Seven Mile Beach and enjoy some of the best snorkeling on Grand Cayman! Visit both a …More

Grand Cayman, Cayman Islands

4.5 (32)

Grand Cayman Kittiwake and Reef Sail

Take a relaxing cruise along the picturesque shores of Seven Mile Beach and enjoy some of the best snorkeling on Grand Cayman! Visit both a...

2 hours 30 minutes Free Cancellation

4.5 (32)

from
$124

No1Sxm Private Intimate Day Sail in St. Maarten

Are you ready to go Sailing? True sailing on board of No1Sxm Trimaran: stable, smooth, fast. The 5 hour experience takes you along the south west …More

4.8 (5)

No1Sxm Private Intimate Day Sail in St. Maarten

Are you ready to go Sailing? True sailing on board of No1Sxm Trimaran: stable, smooth, fast. The 5 hour experience takes you along the south west...

5 hours 30 minutes Free Cancellation

4.8 (5)

from
$124

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

5.0 (44)

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...

4 hours Free Cancellation

5.0 (44)

from
$124

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

4.9 (41)

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...

4 hours Hotel pickup offered Free Cancellation

4.9 (41)

from
$125

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

4.9 (61)