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: Parasailing in Bavaro No1Sxm Private Intimate Day Sail in St. Maarten Don't Worry - Half Day Private Catamaran Cruise - St Maarten Private & Romantic Sunset Cruise Under Sails Private Sunset Tour in Aruba

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 →

St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton

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 (50)

St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton

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 (50)

from
$309

All Inclusive St. John Boating Adventure

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful …More

5.0 (79)

All Inclusive St. John Boating Adventure

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful...

5 hours Hotel pickup offered Free Cancellation

5.0 (79)

from
$314

=Indulge in an exclusive and personalized snorkeling adventure tailored to your desires. Upon arrival at the private pier, enjoy a warm welcome with refreshing cold …More

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

=Indulge in an exclusive and personalized snorkeling adventure tailored to your desires. Upon arrival at the private pier, enjoy a warm welcome with refreshing cold...

3 hours Free Cancellation

from
$327

Luxury Catamaran Private Charter in St. Maarten/St. Martin

Get the mega yacht experience aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a custom-made sailing catamaran appointed with all the …More

5.0 (52)

Luxury Catamaran Private Charter in St. Maarten/St. Martin

Get the mega yacht experience aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a custom-made sailing catamaran appointed with all the...

7 hours 30 minutes Free Cancellation

5.0 (52)

from
$330

Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)

The Virgin Islands are the sailing capital of the world!! Sail with us from St. Thomas to the exotic island of Jost Van Dyke. This …More

5.0 (189)

Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)

The Virgin Islands are the sailing capital of the world!! Sail with us from St. Thomas to the exotic island of Jost Van Dyke. This...

8 hours

5.0 (189)

from
$375

Luxury Catamaran Private Day Sail from St. Maarten to Anguilla

Escape to the tranquil and world-renowned island of Anguilla while you sail aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a …More

5.0 (11)

Luxury Catamaran Private Day Sail from St. Maarten to Anguilla

Escape to the tranquil and world-renowned island of Anguilla while you sail aboard 42ft of pure luxury. Freedom, our brand-new 2022 Lagoon 42 is a...

9 hours 30 minutes Free Cancellation

5.0 (11)

from
$397

Private Tour for Two: Romantic Curacao by Land and Sea

Experience Curacao in the most romantic way possible. This private tour covers both land and sea, and includes equipment, snacks, beverages, and pickup/drop-off at your …More

5.0 (2)

Private Tour for Two: Romantic Curacao by Land and Sea

Experience Curacao in the most romantic way possible. This private tour covers both land and sea, and includes equipment, snacks, beverages, and pickup/drop-off at your...

8 hours

5.0 (2)

from
$447

2 hrs. Private Sunset Sail - South Coast of Puerto Rico

Catch the most amazing sunsets from a secluded spot on the Jobos Bay National Estuarine Research Reserve (JBNERR) with our experienced USCG Captain and crew, …More

5.0 (2)

2 hrs. Private Sunset Sail - South Coast of Puerto Rico

Catch the most amazing sunsets from a secluded spot on the Jobos Bay National Estuarine Research Reserve (JBNERR) with our experienced USCG Captain and crew,...

2 hours Free Cancellation

5.0 (2)

from
$449

Curacao Private Romantic Sunset Sailing Tour for 2

Celebrate love with an unforgettable private romantic sailing experience in beautiful Curacao. Surprise your partner with a breathtaking sunset yacht escape designed for couples seeking …More

5.0 (4)

Curacao Private Romantic Sunset Sailing Tour for 2

Celebrate love with an unforgettable private romantic sailing experience in beautiful Curacao. Surprise your partner with a breathtaking sunset yacht escape designed for couples seeking...

3 hours Free Cancellation

5.0 (4)

from
$479

Sail Away: Private Scenic Excursion from San Juan

Private, AM. PM. or Sunset, sailing around the San Juan Bay and Harbor of Old San Juan, Puerto Rico. (Prices already include all taxes and fees) …More

4.9 (164)

Sail Away: Private Scenic Excursion from San Juan

Private, AM. PM. or Sunset, sailing around the San Juan Bay and Harbor of Old San Juan, Puerto Rico. (Prices already include all taxes and fees)...

2 to 3 hours Free Cancellation

4.9 (164)

from
$494

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

5.0 (30)

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...

3 hours Free Cancellation

5.0 (30)

from
$500

- Private 1.5-hour sunset cruise aboard Kona, a sleek catamaran - Scenic sail along Bermuda’s coastline with golden hour views - Ideal for couples, small …More

5.0 (6)

Bermuda By Sunset “Private Catamaran”

- Private 1.5-hour sunset cruise aboard Kona, a sleek catamaran - Scenic sail along Bermuda’s coastline with golden hour views - Ideal for couples, small...

1 hour 30 minutes Hotel pickup offered Free Cancellation

5.0 (6)

from
$580

Enjoy a unique location to experience a sunset sail and swim in the South Coast Of P.R. in a protected anchorage. …More

5.0 (2)

3 Hours Private Sunset Sail and Swim

Enjoy a unique location to experience a sunset sail and swim in the South Coast Of P.R. in a protected anchorage....

3 hours Free Cancellation

5.0 (2)

from
$580

Private & Romantic Sunset Cruise Under Sails

Sail just offshore of the coast of Grenada. Enjoy snacks and drinks while taking in the remarkable view of the crimson sun falling into the …More

4.9 (17)

Private & Romantic Sunset Cruise Under Sails

Sail just offshore of the coast of Grenada. Enjoy snacks and drinks while taking in the remarkable view of the crimson sun falling into the...

2 hours 30 minutes Free Cancellation

4.9 (17)

from
$608

Best Private Punta Cana Snorkeling Tour & Natural Pool Stop

Indulge in a Private Punta Cana Snorkeling Tour that sets itself apart in every way: 1. Private Transportation: A comfortable minibus will pick you up …More

Punta Cana, Dominican Republic

5.0 (3)

Best Private Punta Cana Snorkeling Tour & Natural Pool Stop

Indulge in a Private Punta Cana Snorkeling Tour that sets itself apart in every way: 1. Private Transportation: A comfortable minibus will pick you up...

3 hours Hotel pickup offered

5.0 (3)

from
$615

We are the only excursion that allows you to drive the boat during this private excursion. We are the only boat that sails in the …More

5.0 (6)

Private Sunset Sail

We are the only excursion that allows you to drive the boat during this private excursion. We are the only boat that sails in the...

2 hours Free Cancellation

5.0 (6)

from
$650

Private Yacht Celebration & Snorkeling Cruise (Open Bar)

"The Ultimate Private Yacht Celebration in Punta Cana! ⚓ Host your next Birthday, Bachelorette Party, Vow Renewal, Family Reunion, Anniversary,, or Special Event aboard your …More

Punta Cana, Dominican Republic

4.6 (82)

Private Yacht Celebration & Snorkeling Cruise (Open Bar)

"The Ultimate Private Yacht Celebration in Punta Cana! ⚓ Host your next Birthday, Bachelorette Party, Vow Renewal, Family Reunion, Anniversary,, or Special Event aboard your...

4 hours Hotel pickup offered Free Cancellation

4.6 (82)

from
$659

Private Day Sail - South Coast of Puerto Rico

Our experienced USCG Captain and crew will make sure you experience the most beautiful and secluded spots of the Jobos Bay National Estuarine Research Reserve …More

4.9 (23)

Private Day Sail - South Coast of Puerto Rico

Our experienced USCG Captain and crew will make sure you experience the most beautiful and secluded spots of the Jobos Bay National Estuarine Research Reserve...

6 hours Free Cancellation

4.9 (23)

from
$680