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Top Caribbean Sailing Trips

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Caribbean Tours

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San Juan Sunset Harbor Boat Ride
Likely to Sell Out
Likely to Sell Out
Isla Verde, Puerto Rico
4.7 (1,418)

San Juan Sunset Harbor Boat Ride

Hop aboard and join us for a captivating journey on a sunset pontoon boat tour, exploring the timeless allure of San Juan Bay, the historical...

1 hour 30 minutes • Hotel pickup offered • Free Cancellation
4.7 (1,418)
from
$99
2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)
Likely to Sell Out
Likely to Sell Out
4.9 (1,125)

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 (1,125)
from
$122
Aruba Sunset Cruise plus Seaside Dinner
4.5 (1,003)

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 (1,003)
from
$122
San Juan Catamaran Sunset Sail with Drinks Included
Likely to Sell Out
Likely to Sell Out
5.0 (666)

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 (666)
from
$119
Tango Caribbean Dinner Cruise
4.8 (504)

Tango Caribbean Dinner Cruise

Experience the true Caribbean way on this evening dinner cruise! Guests are treated to an open bar and snacks as the catamaran sails along the...

3 hours • Free Cancellation
4.8 (504)
from
$85
Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT
4.8 (2,260)

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 (2,260)
from
$119
Aruba Sunset Sail Experience
4.7 (609)

Aruba Sunset Sail Experience

Unwind and end your day on a high note with this relaxing cruise. Climb aboard a comfortable open-deck catamaran and set sail to admire Aruba's...

2 hours • Free Cancellation
4.7 (609)
from
$73
Luxury Lagoon Cruise with Onboard Chef and Signature Cocktails
Likely to Sell Out
Likely to Sell Out
4.9 (288)

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 (288)
from
$149
San Juan: Snorkeling with Turtles and Complimentary Videos
Likely to Sell Out
Likely to Sell Out
4.9 (461)

San Juan: Snorkeling with Turtles and Complimentary Videos

Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginner-friendly adventure led by a professional guide in...

1 hour 30 minutes • Free Cancellation
4.9 (461)
from
$39
Aruba Sunset Catamaran Sail with Appetizers and Open Bar
4.6 (2,194)

Aruba Sunset Catamaran Sail with Appetizers and Open Bar

Experience Aruba's spectacular sunset aboard a luxury catamaran. Enjoy views of Palm Beach from the open water as you sip a cocktail and watch the...

2 hours • Free Cancellation
4.6 (2,194)
from
$92
Arusun Catamaran Sail with Snorkeling in Aruba
Likely to Sell Out
Likely to Sell Out
4.9 (2,556)

Arusun Catamaran Sail with Snorkeling in Aruba

Receive a warm Caribbean welcome aboard Arusun, where our friendly, experienced crew will help you settle in and get ready for 2½ hours of sailing,...

2 hours 30 minutes • Free Cancellation
4.9 (2,556)
from
$63
Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran
Likely to Sell Out
Likely to Sell Out
4.7 (732)

Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran

Welcome aboard the “DOLPHIN”! Join us for an breathtaking sunset sail we’ll make sure it will be the highlight of your vacation! Our professional staff...

2 hours • Free Cancellation
4.7 (732)
from
$59
St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max
5.0 (695)

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 (695)
from
$245
St Kitts Full Day Catamaran to Nevis
4.9 (445)

St Kitts Full Day Catamaran to Nevis

Board your Catamaran for the sailing, snorkeling and beach experience you will never forget! Snorkel in a secluded cove, with all equipment supplied, and attentive...

7 hours • Free Cancellation
4.9 (445)
from
$99
Prickly Pear Catamaran Trip from St Maarten Including Lunch
4.7 (417)

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 (417)
from
$135
Dolphin Catamaran Snorkel and Sail with Open Bar
4.8 (2,705)

Dolphin Catamaran Snorkel and Sail with Open Bar

Enjoy a delightful 3-hour adventure featuring two captivating snorkeling stops. First, explore the iconic shipwreck "Antilla", a fascinating relic resting beneath the azure waters, brimming...

3 hours • Free Cancellation
4.8 (2,705)
from
$69
St. Martin Sunset Sail
4.7 (225)

St. Martin Sunset Sail

Nothing compares to the exquisite colors of a Caribbean sunset. Enjoy the romantic mood that is automatically set as the sun disappears into the waters...

1 hour 30 minutes • Free Cancellation
4.7 (225)
from
$45
Deluxe Half-Day Snorkel Sail on Luxury Catamaran
4.9 (432)

Deluxe Half-Day Snorkel Sail on Luxury Catamaran

Set sail aboard the luxury sailing catamaran Lady Grace to explore the Turks & Caicos Barrier Reef, home to some of the best snorkeling in...

4 hours 30 minutes • Free Cancellation
4.9 (432)
from
$199
Aruba Afternoon Snorkel Sail aboard Palm Pleasure Catamaran
4.7 (310)

Aruba Afternoon Snorkel Sail aboard Palm Pleasure Catamaran

Experience Aruba's magical marine life as you set sail aboard a spacious catamaran and snorkel at two spectacular locations. A friendly crew will take you...

3 hours • Free Cancellation
4.7 (310)
from
$85
Banana Adventure Catamaran Shipwreck Snorkel and Turtle Swim
Likely to Sell Out
Likely to Sell Out
4.8 (221)

Banana Adventure Catamaran Shipwreck Snorkel and Turtle Swim

*Professional and friendly crew* *Snorkeling equipment and safety briefing* *Delicious snacks and refreshments* *Access to the rope swing and diving platform* *Comfortable seating and shaded...

3 hours • Hotel pickup offered • Free Cancellation
4.8 (221)
from
$65

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Good day with very good crew staff!
New York City
Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT
BrunoNifo, Sep 2026
Good day with very good crew staff!
Good day with very good crew staff! The experience was great, good snorkeling and nice stop at the beach!
Read more
Sunset Fun!
New York City
Aruba Sunset Cruise plus Seaside Dinner
Toni_W, Sep 2026
Sunset Fun!
So fun & well organized Super staff Thanks for the fun Andrew, Sam, & Reuben Keep laughing & dancing!
Read more
Safe, Fun and Exciting!
New York City
Dolphin Catamaran Snorkel and Sail with Open Bar
E9610DLmarisam, Sep 2026
Safe, Fun and Exciting!
Jose and Frederick were amazing! They allowed us to have fun with our safety as their first priority. I would definitely go again with these guides.
Read more
Fun
New York City
San Juan: Snorkeling with Turtles and Complimentary Videos
dunkini2026, Sep 2026
Fun
Was a good experience would go again
Read more
Aruba Welcome
New York City
Dolphin Catamaran Snorkel and Sail with Open Bar
Philip_S, Sep 2026
Aruba Welcome
Fantastic tour, they keeper your glass topped off constantly but more than that they were all so friendly and welcoming x
Read more
Great Time
New York City
Tango Caribbean Dinner Cruise
Douglas_A, Sep 2026
Great Time
Great time had by all! Booking, sign in, cruise out, dinner, and cruise back was seamless and issue free. Crew was EXCELLENT and food was great. We will book again!!!
Read more
Snorkeling w/ Turtles!
New York City
Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT
annetN1526IN, Sep 2026
Snorkeling w/ Turtles!
Captain Mike was knowledgeable, the crew was professional, & they were focused #1 on our safety BUT just as important was their focus on our enjoying the experience. The Chief Mate, Nashon, gave an engaging history of local landmarks, buildings & culture. The geography was unmatched in beauty! Now for the best part: snorkeling w/ the sea turtles! We got to see them immediately! We watched a sea turtle eat a jellyfish! And we got to see a spiny star fish! We spotted ALL kinds of local fish species INCLUDING DORY the blue tang! Nashon taught us about all the wildlife we saw. We were treated to food, fun, & Fellowship on the way back. And we OFFICIALLY SAILED THE CARIBBEAN on the way back by securing the engine & sailing under canvas! Special shout out to Leslie for being a top notch Bosun! And the green hand Lane was awesome. 10 outta 10 would recommend! Go get your reservation w/ them ASAP!
Read more
Great experience. My...
New York City
San Juan: Snorkeling with Turtles and Complimentary Videos
Michael_M, Sep 2026
Great experience. My...
Great experience. My girlfriend isnt a great swimmer and they took the time to show her how to snorkel and hold her breath under water. She was very nervous but they were patient and walked us through each step. They made sure she was 100 percent comfortable prior to going out on the water. Recommend this tour 10/10.
Read more
The sunset cruise you don’t want to miss
New York City
San Juan Sunset Harbor Boat Ride
patriciadC306WT, Sep 2026
The sunset cruise you don’t want to miss
I’m so glad I booked this sunset cruise , my family had a blast!! From start to finish it was smooth sailing from pickup to , drop off. The staff on the boat were also phenomenal. It’s so much fun having great people welcome you .Once aboard the party mood is apparent and it’s catchy . You will want to join in. I can’t wait to come back to Puerto Rico , I would definitely say take this cruise and you won’t be disappointed.
Read more
For the cheap price, it’s...
New York City
Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran
Sean_F, Sep 2026
For the cheap price, it’s...
For the cheap price, it’s definitely worth the experience! I was on a cruise stop this day, I took the bus for $5 round trip to Palm beach it was pretty easy to locate.
Read more
Great Staff
New York City
Aruba Sunset Catamaran Sail with Appetizers and Open Bar
Veniece_G, Sep 2026
Great Staff
The staff were very friendly and pleasant and did a great job interacting with the guests. Drinks were great!
Read more
Funday on the Water
New York City
Prickly Pear Catamaran Trip from St Maarten Including Lunch
Michelle_V, Sep 2026
Funday on the Water
It was a fantastic day! Sun was shining, water was refreshing, great snorkeling at prickly pear then ventured to Anguilla. I wish we had more time there to venture the island! I know it’s off season and things are closed but would have been nice to tour around a bit. Overall, the staff were fantastic, music was good, drinks were cold and food was incredible!
Read more
Wonderful boat day!
New York City
St John & Surrounding Cays – Full-Day Sail/Snorkel, 6 Guests Max
Sue_S, Sep 2026
Wonderful boat day!
Kendall was wonderful! Very friendly, knowledgeable, and safety conscious. He knew the best snorkel sites, gauged the sea conditions well and helped with snorkel equipment. The gear was in great shape - like new. Lunch was delicious grilled chicken and homemade pasta salad. Very relaxing, enjoyable boat day!
Read more
Awesome experience
New York City
Prickly Pear Catamaran Trip from St Maarten Including Lunch
DayTrip759501, Sep 2026
Awesome experience
This was an awesome experience. The boat was clean, the crew were fantastic, friendly and attentive and the food was good. But the stops at Prickly Pear Cay and Anguilla were simply gorgeous. Would definitely do this again.
Read more
Another Great Sail - With Red Sail
New York City
Aruba Sunset Catamaran Sail with Appetizers and Open Bar
C3315AStheresas, Sep 2026
Another Great Sail - With Red Sail
Always a first class experience with Red Sail and we particularly enjoyed the Sunset Catamaran Sail. The Open Bar was fun. Do not expect top shelf or wine -- but they did have Balashi Chill canned beer. The staff was engaging and fun. A truly happy experience! I would not hesitate to book with Red Sail.
Read more
Great tour
New York City
Arusun Catamaran Sail with Snorkeling in Aruba
T8313EKrobertg, Sep 2026
Great tour
We had a fantastic time. The snorkeling site was beautiful and the captain, Gabriel, was hilarious and very nice. 10 out of 10!
Read more
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