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: Leisure Full Day Catamaran (Blue, Aqua or LIC) Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten Cruise Sunset Party in Castries Private Luxury Sailing Experience Curacao Curacao: Private Luxury Boat Tour Half Day

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 →

No1Sxm Half Day Sail Snorkeling and Sunset Experience

On this 4-hour sail we have combined the excitement of Sailing on a great trimaran, Swimming/Snorkeling in turquoise waters of a calm bay on the …More

5.0 (4)

No1Sxm Half Day Sail Snorkeling and Sunset Experience

On this 4-hour sail we have combined the excitement of Sailing on a great trimaran, Swimming/Snorkeling in turquoise waters of a calm bay on the...

4 hours Free Cancellation

5.0 (4)

from
$128

Days End Sunset Sail with Open Bar from St. Thomas Ritz-Carlton

Enjoy a relaxing and romantic sail in the calm waters of Pillsbury Sound with views of the beautiful beaches on the north shore of St. …More

4.7 (50)

Days End Sunset Sail with Open Bar from St. Thomas Ritz-Carlton

Enjoy a relaxing and romantic sail in the calm waters of Pillsbury Sound with views of the beautiful beaches on the north shore of St....

1 hour 30 minutes Free Cancellation

4.7 (50)

from
$129

Join us for a 6 Hours yachting, sailing, and snorkeling experience. Your comfort and safety are our main concern. We will do an easy South …More

4.9 (454)

Tropical Catamaran Snorkeling & Sailing

Join us for a 6 Hours yachting, sailing, and snorkeling experience. Your comfort and safety are our main concern. We will do an easy South...

6 hours Free Cancellation

4.9 (454)

from
$129

St. John PiZZA Pi Snorkel Sail with Beach Stop, Lunch & Open Bar - Westin

Join us aboard one of our luxury catamarans, as we set sail for the best snorkeling destinations surrounding St. John. Start the day with a …More

4.9 (173)

St. John PiZZA Pi Snorkel Sail with Beach Stop, Lunch & Open Bar - Westin

Join us aboard one of our luxury catamarans, as we set sail for the best snorkeling destinations surrounding St. John. Start the day with a...

5 hours Free Cancellation

4.9 (173)

from
$129

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

4.8 (29)

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...

7 hours Free Cancellation

4.8 (29)

from
$129

St. Thomas Dinner Sail to Lovango with Open Bar

Step aboard our luxury 65 foot catamaran Lady Lynsey II for an evening escape to the private island of Lovango Cay for dinner under the …More

4.6 (43)

St. Thomas Dinner Sail to Lovango with Open Bar

Step aboard our luxury 65 foot catamaran Lady Lynsey II for an evening escape to the private island of Lovango Cay for dinner under the...

4 hours Free Cancellation

4.6 (43)

from
$129

Discover the Best of St. John - Snorkel, Beach & Shopping!

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

Cruz Bay, US Virgin Islands

4.9 (7)

Discover the Best of St. John - Snorkel, Beach & Shopping!

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

5 hours Hotel pickup offered Free Cancellation

4.9 (7)

from
$129

Barbados -Luxury Cruise with Lunch and Open Bar By Oceanluxx

Discover the pinnacle of luxury aboard Barbados’ newest gem — our 30ft double-decker pontoon boat. Designed for intimate gatherings of up to 15 guests, this …More

4.9 (241)

Barbados -Luxury Cruise with Lunch and Open Bar By Oceanluxx

Discover the pinnacle of luxury aboard Barbados’ newest gem — our 30ft double-decker pontoon boat. Designed for intimate gatherings of up to 15 guests, this...

4 hours Free Cancellation

4.9 (241)

from
$130

Chill and Grill Catamaran Tour in Bonaire

With our Catamaran, we will sail along the beautiful coast of Bonaire and Klein Bonaire. We will stop for our first snorkel experience somewhere in …More

5.0 (522)

Chill and Grill Catamaran Tour in Bonaire

With our Catamaran, we will sail along the beautiful coast of Bonaire and Klein Bonaire. We will stop for our first snorkel experience somewhere in...

5 hours

5.0 (522)

from
$130

Aquaspace Morning Sail and Snorkel Tour on Bonaire with Lunch

Explore the stunning underwater world of Bonaire on this 4-hour morning sail and snorkel tour. Set sail from 09:00 to 13:00, enjoying all-inclusive snacks and …More

5.0 (5)

Aquaspace Morning Sail and Snorkel Tour on Bonaire with Lunch

Explore the stunning underwater world of Bonaire on this 4-hour morning sail and snorkel tour. Set sail from 09:00 to 13:00, enjoying all-inclusive snacks and...

4 hours Free Cancellation

5.0 (5)

from
$130

Tropical Catamaran Snorkeling, Sailing And Beach Experience

Join us for a 6 Hours yachting, sailing, and snorkeling experience. Your comfort and safety are our main concern. We will do an easy South …More

4.9 (320)

Tropical Catamaran Snorkeling, Sailing And Beach Experience

Join us for a 6 Hours yachting, sailing, and snorkeling experience. Your comfort and safety are our main concern. We will do an easy South...

6 hours Free Cancellation

4.9 (320)

from
$132

Private Catamaran Excursion to Sint Maarten with Snorkeling

1. An exceptional natural setting: crystal clear waters and preserved beaches offer an idyllic setting. 2. Marine richness : snorkeling allows you to explore a …More

5.0 (17)

Private Catamaran Excursion to Sint Maarten with Snorkeling

1. An exceptional natural setting: crystal clear waters and preserved beaches offer an idyllic setting. 2. Marine richness : snorkeling allows you to explore a...

8 hours

5.0 (17)

from
$132

3 hour Glow Worm Sunset Cruise from Providenciales

Watch the bioluminescence of glow worms on a spectacular sunset cruise from Providenciales! For a few evenings after the full moon each month, the waters …More

4.7 (160)

3 hour Glow Worm Sunset Cruise from Providenciales

Watch the bioluminescence of glow worms on a spectacular sunset cruise from Providenciales! For a few evenings after the full moon each month, the waters...

3 hours Hotel pickup offered Free Cancellation

4.7 (160)

from
$134

Adults Only Catalina Bay Small Group Snorkel & Sunset Sail

We offer exclusivity and assigned seating, only a small group of people on board, very calm waters. Adults Only On Monday's Afternoon delight Sailing and …More

4.8 (115)

Adults Only Catalina Bay Small Group Snorkel & Sunset Sail

We offer exclusivity and assigned seating, only a small group of people on board, very calm waters. Adults Only On Monday's Afternoon delight Sailing and...

3 hours Free Cancellation

4.8 (115)

from
$135

Prickly Pear Catamaran Trip from St Maarten Including Lunch

Discover the paradise shores of Prickly Pear Islands on this full-day trip from St Maarten. Sail aboard Lambada catamaran and stop at Prickly Pear Island, …More

4.7 (422)

Prickly Pear Catamaran Trip from St Maarten Including Lunch

Discover the paradise shores of Prickly Pear Islands on this full-day trip from St Maarten. Sail aboard Lambada catamaran and stop at Prickly Pear Island,...

8 hours Free Cancellation

4.7 (422)

from
$135

Tropical Sailing Experience with BBQ Lunch or BBQ Dinner in Aruba

Discover Aruba's Beauty Embark on the Tropical Sailing Experience from Varadero Marina Aruba, with morning and afternoon sails available. Cruise past the picturesque Spanish Lagoon, …More

Palm - Eagle Beach, Aruba

4.9 (251)

Tropical Sailing Experience with BBQ Lunch or BBQ Dinner in Aruba

Discover Aruba's Beauty Embark on the Tropical Sailing Experience from Varadero Marina Aruba, with morning and afternoon sails available. Cruise past the picturesque Spanish Lagoon,...

4 hours Hotel pickup offered Free Cancellation

4.9 (251)

from
$135

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

5.0 (67)

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...

4 hours Free Cancellation

5.0 (67)

from
$135

Aruba Sunset Sail Dinner Cruise with Open Bar by Catamaran

Enjoy a 3 hour sunset sail aboard a luxurious catamaran, combining breathtaking views of Aruba’s coastline with a seated dinner and open bar. Welcome aboard …More

4.8 (449)

Aruba Sunset Sail Dinner Cruise with Open Bar by Catamaran

Enjoy a 3 hour sunset sail aboard a luxurious catamaran, combining breathtaking views of Aruba’s coastline with a seated dinner and open bar. Welcome aboard...

3 hours Free Cancellation

4.8 (449)

from
$137

Sailing Adventure Cruise from Montego Bay

Let's go sailing! Imagine diving into the crystal clear waters over a coral reef filled with exotic fish, turtles and starfish. You can even participate in …More

Montego Bay, Jamaica

5.0 (6)

Sailing Adventure Cruise from Montego Bay

Let's go sailing! Imagine diving into the crystal clear waters over a coral reef filled with exotic fish, turtles and starfish. You can even participate in...

4 hours

5.0 (6)

from
$138