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Top 10 Best Caribbean Sailing Trips

Found 366 Sailing Trips activities in Caribbean. Sort by Popularity. - Page 12
 

Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

(5 of 13 reviews)

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea ending in an amazing sunset setting. Great for engagements, and any special private event. Come experience the 1st c... More

Free Cancellation
Start From $229.00
 
Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

  • Caribbean
  • Superb13 reviews5

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the ....

    Free Cancellation
    Start From $229.00
 
 

Private day sail BVI - Explore & enjoy the British Virgin Islands

(5 of 8 reviews)

Enjoy a private day sailing charter and find out what the British Virgin islands are all about. Stunning nature, clear blue water, excellent snorkeling, beautiful beaches and famous beach bars. We customize the tour after your pr... More

Free Cancellation
Private Tour
Start From $2,500.00
 
Private day sail BVI - Explore & enjoy the British Virgin Islands Likely to Sell Out

Private day sail BVI - Explore & enjoy the British Virgin Islands

  • Caribbean
  • Superb8 reviews5

Enjoy a private day sailing charter and find out what the British Virgin islands are all about. Stun....

    Free Cancellation
    Private Tour
    Start From $2,500.00
 
 

Adults Only Aruba Catalina Bay Small-Group Snorkel Sunset Sail

(4.8 of 44 reviews)

We offer assigned seating, only a small group of people on board, very calm waters. Afternoon delight Sailing and Snorkelling Sunset Cruise. We stop at Aruba's most beautiful lagoon, Catalina bay. This is where the water is cr... More

Free Cancellation
Private Tour
Start From $124.99
 
Adults Only Aruba Catalina Bay Small-Group Snorkel Sunset Sail Likely to Sell Out

Adults Only Aruba Catalina Bay Small-Group Snorkel Sunset Sail

  • Caribbean
  • Superb44 reviews4.8

We offer assigned seating, only a small group of people on board, very calm waters. Afternoon deli....

    Free Cancellation
    Private Tour
    Start From $124.99
 
 

4 Hours Party Boat Catamaran Cruise in Negril

(5 of 10 reviews)

Book our unique Catamaran experience. You will be picked up at your hotel. You will be travelling in a comfortable fully air conditioned vehicle from your hotel to Negril. Once you arrive in Negril, you will be escorted to the Cat... More

Free Cancellation
Private Tour
Start From $190.00
 
4 Hours Party Boat Catamaran Cruise in Negril Likely to Sell Out

4 Hours Party Boat Catamaran Cruise in Negril

  • Caribbean
  • Superb10 reviews5

Book our unique Catamaran experience. You will be picked up at your hotel. You will be travelling in....

    Free Cancellation
    Private Tour
    Start From $190.00
 
 

Party in Catamaran in Punta Cana open bar

(4.7 of 21 reviews)

punctuality, respect and dedication for you and your family, we offer you the best party in the Dominican Republic sea  sun, natural pool, music, alcohol. don't let them tell you, do it with us... More

Free Cancellation
Private Tour
Start From $60.00
 
 Party in Catamaran in Punta Cana open bar Likely to Sell Out

Party in Catamaran in Punta Cana open bar

  • Caribbean
  • Superb21 reviews4.7

punctuality, respect and dedication for you and your family, we offer you the best party in the Domi....

    Free Cancellation
    Private Tour
    Start From $60.00
 
 

All Inclusive Day Sail

(4.9 of 90 reviews)

Sailing on Helios in the Virgin Islands can be one of the most memorable days spent on your vacation. The Virgin Islands are a popular destination for sailors, with near-constant trade winds, all-year round high temperatures and ... More

Free Cancellation
Private Tour
Start From $1,800.00
 
All Inclusive Day Sail Likely to Sell Out

All Inclusive Day Sail

  • Caribbean
  • Superb90 reviews4.9

Sailing on Helios in the Virgin Islands can be one of the most memorable days spent on your vacation....

    Free Cancellation
    Private Tour
    Start From $1,800.00
 
 

Horseback Ride and Swim with Catamaran Cruise and Zipline

(4.4 of 13 reviews)

Ride up mountain terrains with spectacular ocean vistas. Journey through Jamaica’s backcountry and pass through farmlands, while exploring the ruins of an 18th century old sugar plantation. Continue to the seaside where your hor... More

Free Cancellation
Private Tour
Start From $199.00
 
Horseback Ride and Swim with Catamaran Cruise and Zipline Likely to Sell Out

Horseback Ride and Swim with Catamaran Cruise and Zipline

  • Caribbean
  • Exellent13 reviews4.4

Ride up mountain terrains with spectacular ocean vistas. Journey through Jamaica’s backcountry and....

    Free Cancellation
    Private Tour
    Start From $199.00
 
 

Mojito - Full Day Private Catamaran Cruise - Sint Maarten

(5 of 12 reviews)

Join us on one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can enjoy all the beauty our island has to offer in the privacy of your own group. Our attentive crew will pamper yo... More

Free Cancellation
Private Tour
Start From $1,000.00
 
Mojito - Full Day Private Catamaran Cruise - Sint Maarten Likely to Sell Out

Mojito - Full Day Private Catamaran Cruise - Sint Maarten

  • Caribbean
  • Superb12 reviews5

Join us on one of our luxury sail catamarans for an amazing day on the water. We offer private chart....

    Free Cancellation
    Private Tour
    Start From $1,000.00
 
 

Ocean Bamboo Rafting Catamaran Cruise and Horseback Ride N Swim

(4.5 of 6 reviews)

It’s Time To Play at CHUKKA OCEAN OUTPOST, where ocean-loving thrill seekers and cultural explorers unite. Your Ocean Bamboo Rafting Triple Pass gives you access to the only seaside nature-adventure park in Jamaica, where you wi... More

Free Cancellation
Private Tour
Start From $209.00
 
Ocean Bamboo Rafting Catamaran Cruise and Horseback Ride N Swim Likely to Sell Out

Ocean Bamboo Rafting Catamaran Cruise and Horseback Ride N Swim

  • Caribbean
  • Exellent6 reviews4.5

It’s Time To Play at CHUKKA OCEAN OUTPOST, where ocean-loving thrill seekers and cultural explorer....

    Free Cancellation
    Private Tour
    Start From $209.00
 
 

Punta Cana Private Cruise up to 10 people

(4.9 of 37 reviews)

Only company with a floating kitchen and large floating bar Our menu options cater to all tastes—including seafood, meat, surf and turf, vegetarian, and more. Coral museum and interpretation center upon arrival Snorkeling are... More

Free Cancellation
Private Tour
Start From $750.00
 
Punta Cana Private Cruise up to 10 people Likely to Sell Out

Punta Cana Private Cruise up to 10 people

  • Caribbean
  • Superb37 reviews4.9

Only company with a floating kitchen and large floating bar Our menu options cater to all tastes—....

    Free Cancellation
    Private Tour
    Start From $750.00
 
 

Private Sailing & Snorkeling Tour with Bar & Food in Fajardo, PR

(5 of 23 reviews)

Explore the offshore islands of the East Coast of Puerto Rico aboard our modern 2013 Beneteau 41 ft Sailboat equipped amenities like full snorkeling gear, paddle boards and floaties. With over 15 years of experience, we'll create ... More

Free Cancellation
Private Tour
Start From $1,298.00
 
Private Sailing & Snorkeling Tour with Bar & Food in Fajardo, PR Likely to Sell Out

Private Sailing & Snorkeling Tour with Bar & Food in Fajardo, PR

  • Caribbean
  • Superb23 reviews5

Explore the offshore islands of the East Coast of Puerto Rico aboard our modern 2013 Beneteau 41 ft ....

    Free Cancellation
    Private Tour
    Start From $1,298.00
 
 

Private Catamaran Cruise Aboard the 'Quetzal'

(5 of 91 reviews)

This private day is yours to tailor! Hand pick off track spots and activities for a full personal experience that the crew will help you design if you wish. Enjoy an exclusive moment with family and friends, and make it a unique d... More

Free Cancellation
Private Tour
Start From $1,990.00
 
Private Catamaran Cruise Aboard the 'Quetzal' Likely to Sell Out

Private Catamaran Cruise Aboard the 'Quetzal'

  • Caribbean
  • Superb91 reviews5

This private day is yours to tailor! Hand pick off track spots and activities for a full personal ex....

    Free Cancellation
    Private Tour
    Start From $1,990.00
 
 

Saona Island Excursion by Catamaran and Speedboat (Full Day)

(3.8 of 8 reviews)

Morning pickup in Punta Cana or Bavaro means you begin the day stress-free. Enjoy the scenery on the way to Bayahibe, where you board either a catamaran for the ride to Saona Island. Upon arrival, you can decide how to spend you... More

Free Cancellation
Private Tour
Start From $95.00
 
Saona Island Excursion by Catamaran and Speedboat (Full Day) Likely to Sell Out

Saona Island Excursion by Catamaran and Speedboat (Full Day)

  • Caribbean
  • Very Good8 reviews3.8

Morning pickup in Punta Cana or Bavaro means you begin the day stress-free. Enjoy the scenery on the....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Small Group: Snorkeling Cruise Adventure around the Punta Cana Coast

(4.7 of 39 reviews)

SINGLES, COUPLES & GROUPS can all explore the beautiful coast of Punta Cana on this safe route. Embark on a party in one of the most beautiful beaches in the world. Take up the warm Punta Cana sun in a spacious double deck catamar... More

Free Cancellation
Private Tour
Start From $64.95
 
Small Group: Snorkeling Cruise Adventure around the Punta Cana Coast Likely to Sell Out

Small Group: Snorkeling Cruise Adventure around the Punta Cana Co....

  • Caribbean
  • Superb39 reviews4.7

SINGLES, COUPLES & GROUPS can all explore the beautiful coast of Punta Cana on this safe route. Emba....

    Free Cancellation
    Private Tour
    Start From $64.95
 
 

Saona Island Tour and Catamaran Party from Punta Cana

(4 of 6 reviews)

Saona Island is like a paradise on earth surrounded by white sand beaches, crystal clear turquoise waters and countless palm trees, this environment invites you to relax. The tour of Saona Island is an experience of a lifetime! T... More

Free Cancellation
Private Tour
Start From $74.00
 
Saona Island Tour and Catamaran Party from Punta Cana Likely to Sell Out

Saona Island Tour and Catamaran Party from Punta Cana

  • Caribbean
  • Very Good6 reviews4

Saona Island is like a paradise on earth surrounded by white sand beaches, crystal clear turquoise w....

    Free Cancellation
    Private Tour
    Start From $74.00
 
 

Snorkeling Adventure and Explore Catalina Island from Punta Cana

(3.6 of 5 reviews)

Spend the day cruising off the Dominican Republic’s coast on a Catamaran bound for Catalina Island. Listen to live music and sip drinks from the open bar before diving in to snorkel on “The Wall” with the snorkel equipment p... More

Free Cancellation
Private Tour
Start From $80.00
 
Snorkeling Adventure and Explore Catalina Island from Punta Cana Likely to Sell Out

Snorkeling Adventure and Explore Catalina Island from Punta Cana

  • Caribbean
  • Very Good5 reviews3.6

Spend the day cruising off the Dominican Republic’s coast on a Catamaran bound for Catalina Island....

    Free Cancellation
    Private Tour
    Start From $80.00
 
 

Fun Package Parasailing & Party Boat From Punta Cana

(3.3 of 3 reviews)

Imagine being raised 150 feet in the air, the cool wind caressing your face while relaxing with a spectacular view of the coast of Bavaro - Punta Cana. Stop imagining and join us in the exciting ride of parasailing, a truly unforg... More

Free Cancellation
Skip The Line
Private Tour
Start From $138.00
 
Fun Package Parasailing & Party Boat From Punta Cana Likely to Sell Out

Fun Package Parasailing & Party Boat From Punta Cana

  • Caribbean
  • Good3 reviews3.3

Imagine being raised 150 feet in the air, the cool wind caressing your face while relaxing with a sp....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $138.00
 
 

7 Hour Private Catamaran Sail, Snorkel and Beach BBQ Grace Bay, Providenciales

(5 of 17 reviews)

GO NATIVE! Take a journey into the culinary culture of the Turks and Caicos as we take you on an informative, scenic and relaxing full day sailing adventure. Experience true sailing and an educational guided snorkel tour of the wo... More

Free Cancellation
Skip The Line
Private Tour
Start From $5,320.00
 
7 Hour Private Catamaran Sail, Snorkel and Beach BBQ Grace Bay, Providenciales Likely to Sell Out

7 Hour Private Catamaran Sail, Snorkel and Beach BBQ Grace Bay, P....

  • Caribbean
  • Superb17 reviews5

GO NATIVE! Take a journey into the culinary culture of the Turks and Caicos as we take you on an inf....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $5,320.00
 
 

St Martin Gd-Case: Private day in all inclusive catamaran

(5 of 10 reviews)

Imagine a perfect day, lulled by the waves and rays of the sun, aboard our exceptional catamaran that transforms every moment into an unforgettable adventure. This catamaran combines comfort, performance and space, offering a uniq... More

Free Cancellation
Skip The Line
Private Tour
Start From $271.39
 
St Martin Gd-Case: Private day in all inclusive catamaran Likely to Sell Out

St Martin Gd-Case: Private day in all inclusive catamaran

  • Caribbean
  • Superb10 reviews5

Imagine a perfect day, lulled by the waves and rays of the sun, aboard our exceptional catamaran tha....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $271.39
 
 

Be Happy - Private Catamaran Cruise in Sint Maarten - Half Day

(5 of 1 review)

Join us on Be Happy, one of our luxury sail catamarans for an amazing day on the water. We offer private charters where you can enjoy all the beauty our island has to offer in the privacy of your own group. Our attentive crew will... More

Free Cancellation
Skip The Line
Private Tour
Start From $770.00
 
Be Happy - Private Catamaran Cruise in Sint Maarten - Half Day Likely to Sell Out

Be Happy - Private Catamaran Cruise in Sint Maarten - Half Day

  • Caribbean
  • Superb1 review5

Join us on Be Happy, one of our luxury sail catamarans for an amazing day on the water. We offer pri....

    Free Cancellation
    Skip The Line
    Private Tour
    Start From $770.00
 
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