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 →

Best Luxury Catamaran Day Sail St Maarten on The Phoenix (Public)

Step aboard The Phoenix, a spacious sailing catamaran, and spend five unforgettable hours exploring the beautiful coastline of Sint Maarten. Relax on the sundeck with …More

4.9 (1,077)

Best Luxury Catamaran Day Sail St Maarten on The Phoenix (Public)

Step aboard The Phoenix, a spacious sailing catamaran, and spend five unforgettable hours exploring the beautiful coastline of Sint Maarten. Relax on the sundeck with...

5 hours Free Cancellation

4.9 (1,077)

from
$139

All-Inclusive Sunset Sail - Semi Private - Only 6 Guests

An Unforgettable Sailing Experience, Just for You. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us …More

5.0 (103)

All-Inclusive Sunset Sail - Semi Private - Only 6 Guests

An Unforgettable Sailing Experience, Just for You. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us...

2 hours Free Cancellation

5.0 (103)

from
$139

Negril PRIVATE CHARTER Catamaran (rate for 21 persons)

The minimum persons required to pay is 21 The private charter can accommodate up to 120 persons You may choose any 2 stops from the …More

Negril, Jamaica

4.9 (14)

Negril PRIVATE CHARTER Catamaran (rate for 21 persons)

The minimum persons required to pay is 21 The private charter can accommodate up to 120 persons You may choose any 2 stops from the...

4 hours Hotel pickup offered

4.9 (14)

from
$139

St Thomas Pizza Pi Snorkel Sail From Frenchman's Reef

Start the day with a sail to an offshore cay for premier snorkeling. In addition to fruit, salads, and cookies, our main lunch will be …More

5.0 (2)

St Thomas Pizza Pi Snorkel Sail From Frenchman's Reef

Start the day with a sail to an offshore cay for premier snorkeling. In addition to fruit, salads, and cookies, our main lunch will be...

5 hours Free Cancellation

5.0 (2)

from
$139

Punta Cana Parasailing & Snorkeling Cruise Experience

Surprise yourself in this combination of two great excursions. While the clear water splashes your feet, fly 500 feet high and enjoy a spectacular panoramic …More

Punta Cana, Dominican Republic

4.8 (619)

Punta Cana Parasailing & Snorkeling Cruise Experience

Surprise yourself in this combination of two great excursions. While the clear water splashes your feet, fly 500 feet high and enjoy a spectacular panoramic...

4 hours 30 minutes Hotel pickup offered Free Cancellation

4.8 (619)

from
$140

Beach Trip Along The West Coast Of Curacao

Sailing along Curacao’s West Coast on the biggest catamaran of Curacao is a must do attraction! The trip starts at 08:30 am. As soon as …More

4.9 (44)

Beach Trip Along The West Coast Of Curacao

Sailing along Curacao’s West Coast on the biggest catamaran of Curacao is a must do attraction! The trip starts at 08:30 am. As soon as...

8 hours Free Cancellation

4.9 (44)

from
$140

No1SXM Day Sailing Experience 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

4.9 (153)

No1SXM Day Sailing Experience 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

4.9 (153)

from
$145

Learn how to operate and sail a Hobie Cat Wave or Hobie Cat Getaway like a true skipper. Your expert teacher will be a certified …More

4.5 (10)

Hobie Cat Sailing Lesson

Learn how to operate and sail a Hobie Cat Wave or Hobie Cat Getaway like a true skipper. Your expert teacher will be a certified...

1 hour 30 minutes Free Cancellation

4.5 (10)

from
$145

RICKS CAFE PARTY CRUISE RIU AQUARELLE with Open Bar & DJ

ARE YOUR READY TO PARTY... this is Strictly and adults only cruise, From the moment you're picked up from the hotel your tour of Jamaica …More

Falmouth, Jamaica

4.7 (3)

RICKS CAFE PARTY CRUISE RIU AQUARELLE with Open Bar & DJ

ARE YOUR READY TO PARTY... this is Strictly and adults only cruise, From the moment you're picked up from the hotel your tour of Jamaica...

7 to 8 hours Hotel pickup offered Free Cancellation

4.7 (3)

from
$145

4 Hour Catamaran Sail and Snorkel Tour from Grace Bay

Set sail for a relaxing Caribbean journey on this half-day cruise and snorkeling excursion from Providenciales. Hop aboard a world-class catamaran, operated by a friendly …More

4.9 (1,531)

4 Hour Catamaran Sail and Snorkel Tour from Grace Bay

Set sail for a relaxing Caribbean journey on this half-day cruise and snorkeling excursion from Providenciales. Hop aboard a world-class catamaran, operated by a friendly...

4 hours Hotel pickup offered Free Cancellation

4.9 (1,531)

from
$146

Luxury Lagoon Cruise with Onboard Chef and Signature Cocktails

The Luxury Lagoon Cruise allows you to cruise along Aruba’s Southern Coast aboard our Teak Schooner. While cruising, join us by the bar for a …More

4.9 (295)

Luxury Lagoon Cruise with Onboard Chef and Signature Cocktails

The Luxury Lagoon Cruise allows you to cruise along Aruba’s Southern Coast aboard our Teak Schooner. While cruising, join us by the bar for a...

5 hours Free Cancellation

4.9 (295)

from
$149

Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin St. John

Join us for a day of sailing and snorkeling aboard one of our luxury catamarans and enjoy a sun-filled day topped off with lunch at …More

4.9 (350)

Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin St. John

Join us for a day of sailing and snorkeling aboard one of our luxury catamarans and enjoy a sun-filled day topped off with lunch at...

6 hours 30 minutes Free Cancellation

4.9 (350)

from
$149

The Original Eco Tour Full-Day Around the Island of Sint Maarten

Enjoy a full day sailing aboard Too Rhum Punch or Quality Time our friendly comfortable and Fun Catamaran around the island of Sint Maarten / …More

4.9 (553)

The Original Eco Tour Full-Day Around the Island of Sint Maarten

Enjoy a full day sailing aboard Too Rhum Punch or Quality Time our friendly comfortable and Fun Catamaran around the island of Sint Maarten /...

8 hours Free Cancellation

4.9 (553)

from
$149

Punta Cana Combo Tour: Snorkeling, Catamaran Cruise & Parasailing

Enjoy a 500 feet high panoramic view of the entire coastline and turquoise waters of Bavaro Beach through an exciting parasailing flight. Relax and spend …More

Punta Cana, Dominican Republic

4.7 (1,015)

Punta Cana Combo Tour: Snorkeling, Catamaran Cruise & Parasailing

Enjoy a 500 feet high panoramic view of the entire coastline and turquoise waters of Bavaro Beach through an exciting parasailing flight. Relax and spend...

4 hours 30 minutes Hotel pickup offered Free Cancellation

4.7 (1,015)

from
$149

Half Day Sail and Snorkel with the Turtles

Snorkel and Sail with the USCG Licensed Crew aboard the Sailing Yacht "FURY", a beautifully restored Morgan 46' Ketch. We actually "SAIL" out to the …More

4.9 (300)

Half Day Sail and Snorkel with the Turtles

Snorkel and Sail with the USCG Licensed Crew aboard the Sailing Yacht "FURY", a beautifully restored Morgan 46' Ketch. We actually "SAIL" out to the...

3 hours 30 minutes Free Cancellation

4.9 (300)

from
$149

St. Thomas Dinner Sail to St. John with Open Bar - Ritz-Carlton

Step aboard our luxury 53 foot catamaran for an evening escape to the island of St. John. This popular sail departs directly from The Ritz-Carlton …More

4.7 (56)

St. Thomas Dinner Sail to St. John with Open Bar - Ritz-Carlton

Step aboard our luxury 53 foot catamaran for an evening escape to the island of St. John. This popular sail departs directly from The Ritz-Carlton...

5 hours Free Cancellation

4.7 (56)

from
$149

What makes our trip unique is the rare opportunity to snorkel at both the pristine waters of St. John’s National Park and a remote, uninhabited …More

4.9 (1,056)

Snorkel Cat All Inclusive Adventure

What makes our trip unique is the rare opportunity to snorkel at both the pristine waters of St. John’s National Park and a remote, uninhabited...

5 hours Free Cancellation

4.9 (1,056)

from
$150

Hands on Sailing Tour in Rodney Bay St Lucia

Enjoy an exciting and adrenaline filled sail around Rodney Bay or further afield, learning the skills and techniques of sailing a race yacht. As you …More

4.9 (51)

Hands on Sailing Tour in Rodney Bay St Lucia

Enjoy an exciting and adrenaline filled sail around Rodney Bay or further afield, learning the skills and techniques of sailing a race yacht. As you...

3 hours Free Cancellation

4.9 (51)

from
$150

Good Times Too Premium Catamaran Lunch Cruise

Our Lunch cruise on Good Times Too offers limited numbers of passengers of 20 persons. We start from the west coast (not Bridgetown) with the …More

5.0 (244)

Good Times Too Premium Catamaran Lunch Cruise

Our Lunch cruise on Good Times Too offers limited numbers of passengers of 20 persons. We start from the west coast (not Bridgetown) with the...

5 hours Hotel pickup offered Free Cancellation

5.0 (244)

from
$154

Leisure Full Day Catamaran (Blue, Aqua or LIC)

Crafted Catamarans: Specifically designed for water tours, comfort, spacious decks, shaded seating areas, bar, and restroom for the enjoyment of passengers. Scenic Coastal Routes: Allowing …More

5.0 (32)

Leisure Full Day Catamaran (Blue, Aqua or LIC)

Crafted Catamarans: Specifically designed for water tours, comfort, spacious decks, shaded seating areas, bar, and restroom for the enjoyment of passengers. Scenic Coastal Routes: Allowing...

7 hours Hotel pickup offered Free Cancellation

5.0 (32)

from
$155