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Top Caribbean Sailing Trips

262 Results
Party Boat: Drinks & Snorkeling in Punta Cana

Enjoy a half day on board of a catamaran along the coast of Punta Cana. an unforgettable day at the beach on the paradisiacal coasts …More

Punta Cana, Dominican Republic

Enjoy a half day on board of a catamaran along the coast of Punta Cana. an unforgettable day at the beach on the paradisiacal coasts...

2 hours 30 minutes Hotel pickup offered Free Cancellation
4.8 (4)
from
$110
Exclusive Hip Hop Punta Cana Party Boat with Open Bar *Only Adult

We are one of the best party boat in the coast area with the best entertainement team , our professional certified team we provide the …More

Punta Cana, Dominican Republic

We are one of the best party boat in the coast area with the best entertainement team , our professional certified team we provide the...

3 hours 30 minutes Hotel pickup offered
5.0 (4)
from
$6,400
Hip Hop Party boat booze cruise w Open Bar (adults only)

Enjoy a fun party atmosphere in our 3 hour all you can drink hip hop party boat cruise. A quick stop for snorkeling, drinks in …More

Enjoy a fun party atmosphere in our 3 hour all you can drink hip hop party boat cruise. A quick stop for snorkeling, drinks in...

3 hours Hotel pickup offered Free Cancellation
5.0 (4)
from
$65
I Like Turtles Private Sailing and Snorkeling from Sapphire

Come sail on a beautiful classic monohaul sailboat. You're guaranteed to enjoy your day sailing and snorkeling with amazing green sea turtles here in the …More

Likely to Sell Out
Likely to Sell Out

Come sail on a beautiful classic monohaul sailboat. You're guaranteed to enjoy your day sailing and snorkeling with amazing green sea turtles here in the...

3 hours Free Cancellation
5.0 (3)
from
$799
Private Angelfish Snorkeling with Brunch in Aruba

You are cordially invited to indulge yourself in the privacy and comfort of an Aruba sailing charter! Whatever your desires, the crew of the Tropical …More

Palm - Eagle Beach, Aruba

You are cordially invited to indulge yourself in the privacy and comfort of an Aruba sailing charter! Whatever your desires, the crew of the Tropical...

3 hours Hotel pickup offered Free Cancellation
5.0 (3)
from
$707
SPECIAL - (Up to 4 Passengers) 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 (3)
from
$1,347
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

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
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

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
Private Luxury Veuve Clicquot Sunset Champagne Yacht Charter

Your private group up to 12 individuals will enjoy a Luxury Sunset and Champagne cruise about our luxury 50' Voyage catamaran. We head out early …More

Likely to Sell Out
Likely to Sell Out

Your private group up to 12 individuals will enjoy a Luxury Sunset and Champagne cruise about our luxury 50' Voyage catamaran. We head out early...

2 hours Free Cancellation
5.0 (2)
from
$1,495
2 days 1 night by private catamaran from St Martin to St Barth

Treat yourself to a private and exclusive stay in Saint Barthélémy from Grand-Case Combine sailing, discovering a part of St Martin by sea, magical night …More

Treat yourself to a private and exclusive stay in Saint Barthélémy from Grand-Case Combine sailing, discovering a part of St Martin by sea, magical night...

2 days
5.0 (2)
from
$4,798
Full-Day Private Boat Charter Caribbean adventure

A timeless adventure aboard DE our sailboat. Come live an unforgettable experience on a sailboat. No DE engines, sail like pirates. Decks DE stern and …More

A timeless adventure aboard DE our sailboat. Come live an unforgettable experience on a sailboat. No DE engines, sail like pirates. Decks DE stern and...

6 hours Free Cancellation
5.0 (2)
from
$1,779
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

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
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

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
2.5hr Private Catamaran Cruise with Snorkeling, Bar, Food

Experience the exclusivity of a private catamaran charter with Aristo Kat Tours Ltd. By booking private, you will create your own vibe - select your …More

Experience the exclusivity of a private catamaran charter with Aristo Kat Tours Ltd. By booking private, you will create your own vibe - select your...

2 hours 30 minutes Free Cancellation
5.0 (2)
from
$2,900
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

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
Saona by Speedboat: Private Beach & Snorkeling – Small Group

Enjoy Saona Island away from the crowds on a private beach reserved just for your small group. Snorkel in turquoise waters, relax under palm trees, …More

La Romana, Dominican Republic

Enjoy Saona Island away from the crowds on a private beach reserved just for your small group. Snorkel in turquoise waters, relax under palm trees,...

7 hours 30 minutes Hotel pickup offered Free Cancellation
5.0 (2)
from
$115
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. …More

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 Sunset Charter on Wyuna Catamaran

At Sail Bermuda, a sunset charter isn’t just a sail—it’s your own private escape, curated with care. You’ll glide across calm waters aboard the luxury …More

Likely to Sell Out
Likely to Sell Out

At Sail Bermuda, a sunset charter isn’t just a sail—it’s your own private escape, curated with care. You’ll glide across calm waters aboard the luxury...

3 hours Free Cancellation
5.0 (1)
from
$2,150
Mojito - Half Day Private Catamaran Cruise - St Maarten

Join us aboard Mojito, one of our luxury sailing catamarans, for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private …More

Join us aboard Mojito, one of our luxury sailing catamarans, for an unforgettable half-day charter on the beautiful waters of St. Maarten! Enjoy a private...

4 hours Free Cancellation
5.0 (1)
from
$190
Boat Cruise to the French Islands

Spend the day in Les Saintes or Guadeloupe or Martinique or Marie Galante (French Islands) relaxing on the beach of just being in the French …More

Spend the day in Les Saintes or Guadeloupe or Martinique or Marie Galante (French Islands) relaxing on the beach of just being in the French...

8 to 10 hours Hotel pickup offered
5.0 (1)
from
$2,500

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