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: Private 4 hour Catamaran Tour Private Sunset Sail, Open Bar, 12 Guests, Amazing Island Views Private, Skippered Catamaran Day Trip in Grenada Sail and Snorkel at Cades Reef Be Happy - Half Day Private Catamaran Cruise - St Maarten

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 →

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea ending in an amazing sunset setting. …More

Fajardo, Puerto Rico

4.9 (21)

Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea ending in an amazing sunset setting....

3 hours Free Cancellation

4.9 (21)

from
$229

Mojito - Full Day Private Catamaran Cruise - St Maarten

Join us on Mojito one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can enjoy …More

4.8 (24)

Mojito - Full Day Private Catamaran Cruise - St Maarten

Join us on Mojito one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can enjoy...

8 hours Free Cancellation

4.8 (24)

from
$230

Be Happy - Full Day Private Catamaran Cruise - St Maarten

Join us on Be Happy, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can …More

5.0 (9)

Be Happy - Full Day Private Catamaran Cruise - St Maarten

Join us on Be Happy, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can...

8 hours Free Cancellation

5.0 (9)

from
$235

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

Join us on Don't Worry, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can …More

5.0 (16)

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

Join us on Don't Worry, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can...

8 hours Free Cancellation

5.0 (16)

from
$235

Private Catamaran Excursion in Anguilla with its Turquoise Waters

looking for new adventures, unforgettable experience and relaxing beach ? sail with us around Saint-Martin and its neighboring islands. we assure you a memorable experience. …More

5.0 (19)

Private Catamaran Excursion in Anguilla with its Turquoise Waters

looking for new adventures, unforgettable experience and relaxing beach ? sail with us around Saint-Martin and its neighboring islands. we assure you a memorable experience....

8 hours

5.0 (19)

from
$240

St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max

An Unforgettable Sailing Experience! We offer a Semi-private and all inclusive Day trip that will be the best day of your vacation. There is no …More

5.0 (700)

St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max

An Unforgettable Sailing Experience! We offer a Semi-private and all inclusive Day trip that will be the best day of your vacation. There is no...

6 hours 30 minutes Free Cancellation

5.0 (700)

from
$245

Jost Van Dyke - Sandy Spit & Soggy Dollar Sailing Tour in the BVI

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

Tortola, British Virgin Islands

5.0 (110)

Jost Van Dyke - Sandy Spit & Soggy Dollar Sailing Tour in the BVI

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

6 hours Free Cancellation

5.0 (110)

from
$245

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

5.0 (32)

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...

2 hours 30 minutes Free Cancellation

5.0 (32)

from
$245

Amazing Half Day Private Boat Charter on Luxury Sailing Catamaran

Swim and snorkel beautiful reefs. See the amazing beaches and Islands while catching some sun on the bean bags on top of the trampolines. You …More

5.0 (12)

Amazing Half Day Private Boat Charter on Luxury Sailing Catamaran

Swim and snorkel beautiful reefs. See the amazing beaches and Islands while catching some sun on the bean bags on top of the trampolines. You...

4 hours 30 minutes Free Cancellation

5.0 (12)

from
$250

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

5.0 (36)

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...

4 hours Free Cancellation

5.0 (36)

from
$260

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

5.0 (25)

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...

4 hours Free Cancellation

5.0 (25)

from
$260

Deluxe 2-Hour Private Charter in Montego Bay with Open Bar

Escape to a Private Paradise Begin your day with a personalised welcome at our secluded pier, where refreshing cold towels and dedicated concierge service await. …More

5.0 (3)

Deluxe 2-Hour Private Charter in Montego Bay with Open Bar

Escape to a Private Paradise Begin your day with a personalised welcome at our secluded pier, where refreshing cold towels and dedicated concierge service await....

3 hours Free Cancellation

5.0 (3)

from
$273

** This trip departs from St. Thomas Only ** Get ready for a day of sun, sea, and stories! Our crew members, who also call …More

5.0 (441)

6-Hour Turtles, Pizza Pi & Sunset Sail

** This trip departs from St. Thomas Only ** Get ready for a day of sun, sea, and stories! Our crew members, who also call...

6 hours

5.0 (441)

from
$280

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

Exclusive Caribbean Sunset Escape Experience unparalleled luxury and seclusion on a 2-hour private yacht charter. Personalised Welcome Arrive at our secluded pier and enjoy: - …More

5.0 (1)

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

Exclusive Caribbean Sunset Escape Experience unparalleled luxury and seclusion on a 2-hour private yacht charter. Personalised Welcome Arrive at our secluded pier and enjoy: -...

2 hours Free Cancellation

5.0 (1)

from
$280

A day with Max Charters is a unique way to experience the Virgin Islands. We carry fewer passengers than most charter companies in order to …More

5.0 (136)

Full Day Sail with Max Charters

A day with Max Charters is a unique way to experience the Virgin Islands. We carry fewer passengers than most charter companies in order to...

6 hours Free Cancellation

5.0 (136)

from
$285

Full-Day Sailing Tour in Virgin Islands National Park

Set sail and explore the Virgin Islands National Park! Enjoy a day of sailing and snorkeling with lunch and drinks provided! Where to meet: We …More

4.9 (49)

Full-Day Sailing Tour in Virgin Islands National Park

Set sail and explore the Virgin Islands National Park! Enjoy a day of sailing and snorkeling with lunch and drinks provided! Where to meet: We...

6 hours Free Cancellation

4.9 (49)

from
$285

Curacao Private Luxury Boat & Lunch Experience

Create unforgettable memories with Maxie Sailing! We specialize in private luxury sailing experiences in Curacao, offering everything from relaxed family cruises to romantic escapes in …More

5.0 (4)

Curacao Private Luxury Boat & Lunch Experience

Create unforgettable memories with Maxie Sailing! We specialize in private luxury sailing experiences in Curacao, offering everything from relaxed family cruises to romantic escapes in...

5 hours Free Cancellation

5.0 (4)

from
$285

St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast - Westin

This one of a kind excursion to Jost Van Dyke allows passengers to spend the most time on the island out of all other group …More

4.9 (207)

St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast - Westin

This one of a kind excursion to Jost Van Dyke allows passengers to spend the most time on the island out of all other group...

8 hours Free Cancellation

4.9 (207)

from
$289

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea. Great for birthdays and any special …More

Fajardo, Puerto Rico

5.0 (175)

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea. Great for birthdays and any special...

5 hours Free Cancellation

5.0 (175)

from
$299