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Top Caribbean Sailing Trips

262 Results
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

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
SPECIAL - All Inclusive Day Sail

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

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
5.0 (1)
from
$1,550
Turtles Guaranteed! Fuel Price Included. Smooth, Comfortable Ride

We would love to host you all and show you a wonderful day on the water! This itinerary is set to maximize witnessing the beauty …More

We would love to host you all and show you a wonderful day on the water! This itinerary is set to maximize witnessing the beauty...

5 hours Free Cancellation
5.0 (1)
from
$1,300
Exotic River Rafting and Luminous Lagoon Adventure

-“Rafter’s Village”, is on 6 acres of beautifully manicured lawns situated on a natural island. It offers a full recreational facility which includes picnic grounds, …More

Ocho Rios, Jamaica

-“Rafter’s Village”, is on 6 acres of beautifully manicured lawns situated on a natural island. It offers a full recreational facility which includes picnic grounds,...

4 hours Hotel pickup offered Free Cancellation
5.0 (1)
from
$99
Saona Island Day Trip From Punta Cana with Lunch and Open Bar

Explore the remarkable Altos de Chavon and dig your toes in the sand of Saona Island during this full-day excursion from Punta Cana, available every …More

Punta Cana, Dominican Republic

Explore the remarkable Altos de Chavon and dig your toes in the sand of Saona Island during this full-day excursion from Punta Cana, available every...

9 hours Hotel pickup offered Free Cancellation
4.5 (2,643)
from
$82
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 …More

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 (2,266)
from
$92
Morning Snorkel Sail with Premium Champagne Brunch

Start your day with a relaxed catamaran sail along Aruba’s turquoise coast, paired with a fresh mimosa brunch on board. With multiple snorkeling stops at …More

Start your day with a relaxed catamaran sail along Aruba’s turquoise coast, paired with a fresh mimosa brunch on board. With multiple snorkeling stops at...

4 hours Free Cancellation
4.7 (2,136)
from
$85
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 …More

Likely to Sell Out
Likely to Sell Out
Isla Verde, Puerto Rico

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 (1,432)
from
$99
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 …More

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 (1,019)
from
$122
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

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 (1,014)
from
$149
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 …More

Likely to Sell Out
Likely to Sell Out

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 (763)
from
$59
Historical San Juan Bay Sunset Sailing Tour

Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind, the peace from no engine noise, no …More

Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind, the peace from no engine noise, no...

2 hours Free Cancellation
4.7 (725)
from
$119
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 …More

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 (640)
from
$73
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 …More

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
4.7 (515)
from
$85
Jolly Pirate Afternoon Sail with Snorkeling

Enjoy an afternoon snorkeling cruise in Aruba aboard this 85-foot teak Schooner. Visit three great sites: Malmok Reefs, Boca Catalina and the WWII shipwreck, Antilla! You can choose to swim …More

Enjoy an afternoon snorkeling cruise in Aruba aboard this 85-foot teak Schooner. Visit three great sites: Malmok Reefs, Boca Catalina and the WWII shipwreck, Antilla! You can choose to swim...

3 hours
4.7 (512)
from
$89
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

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
Aruba Sunset Sail with Open Bar

With this trip you will sail along Aruba's scenic coastline and enjoy the most spectacular and fun sunset aboard our luxurious catamaran. …More

With this trip you will sail along Aruba's scenic coastline and enjoy the most spectacular and fun sunset aboard our luxurious catamaran....

2 hours Free Cancellation
4.7 (372)
from
$112
Snorkel with Turtles at WW2 Shipwreck Includes Sunset & BBQ

Step aboard on one of the famous Spronk designs Catamarans and enjoy the longest sailing tour on the island 4.5 unforgettable hours on the Caribbean …More

Palm - Eagle Beach, Aruba

Step aboard on one of the famous Spronk designs Catamarans and enjoy the longest sailing tour on the island 4.5 unforgettable hours on the Caribbean...

4 hours 30 minutes Hotel pickup offered Free Cancellation
4.7 (365)
from
$119
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 …More

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 (318)
from
$90
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 …More

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 (230)
from
$45

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