Menu

Top 10 Best Caribbean Sailing Trips

Found 379 Sailing Trips activities in Caribbean. Sort by Popularity.
 

Dolphin Catamaran Snorkel and Sail with Open Bar

(4.7 of 2,243 reviews)

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 with tales of maritime history and intri... More

Free Cancellation
Start From $69.00
 
Dolphin Catamaran Snorkel and Sail with Open Bar

Dolphin Catamaran Snorkel and Sail with Open Bar

  • Caribbean
  • Superb2,243 reviews4.7

Enjoy a delightful 3-hour adventure featuring two captivating snorkeling stops. First, explore the i....

    Free Cancellation
    Start From $69.00
 
 

Nassau: Swimming Pigs & Island Escape with Bahamian Lunch

(4.7 of 1,201 reviews)

Get ready for an unforgettable island escape from Nassau with the world-famous swimming pigs of the Bahamas. Your half day adventure takes you to stunning Rose Island, where crystal clear waters, soft white sand, and friendly pigs... More

Free Cancellation
Start From $149.00
 
Nassau: Swimming Pigs & Island Escape with Bahamian Lunch

Nassau: Swimming Pigs & Island Escape with Bahamian Lunch

  • Caribbean
  • Superb1,201 reviews4.7

Get ready for an unforgettable island escape from Nassau with the world-famous swimming pigs of the ....

    Free Cancellation
    Start From $149.00
 
 

5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

(4.9 of 890 reviews)

Come aboard the sailing catamaran "The Phoenix" and leave everything behind. Sail through the stunning sights of St. Maarten, indulge in drinks and fine food - we offer fruits and cake for breakfast and freshly cooked lunch. Enjoy... More

Free Cancellation
Start From $139.00
 
5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

  • Caribbean
  • Superb890 reviews4.9

Come aboard the sailing catamaran "The Phoenix" and leave everything behind. Sail through the stunni....

    Free Cancellation
    Start From $139.00
 
 

Saona Island Day Trip From Punta Cana with Lunch and Open Bar

(4.3 of 2,631 reviews)

Experience a stunning day trip to Saona Island! Your adventure begins with a convenient pick-up from your hotel. Travel by catamaran, enjoying the scenic views and lively atmosphere sipping drinks from the open bar and dancing to ... More

Free Cancellation
Start From $82.00
 
Saona Island Day Trip From Punta Cana with Lunch and Open Bar

Saona Island Day Trip From Punta Cana with Lunch and Open Bar

  • Caribbean
  • Exellent2,631 reviews4.3

Experience a stunning day trip to Saona Island! Your adventure begins with a convenient pick-up from....

    Free Cancellation
    Start From $82.00
 
 

San Juan Sunset Harbor Boat Ride

(4.6 of 1,293 reviews)

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 gem of Puerto Rico. Our Sunset Tour offers a perfect fusion of cultural exploration, a... More

Free Cancellation
Start From $109.00
 
San Juan Sunset Harbor Boat Ride

San Juan Sunset Harbor Boat Ride

  • Caribbean
  • Superb1,293 reviews4.6

Hop aboard and join us for a captivating journey on a sunset pontoon boat tour, exploring the timele....

    Free Cancellation
    Start From $109.00
 
 

Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran

(4.7 of 614 reviews)

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 will give you the ultimate service to ensure you’ll have the time of y... More

Free Cancellation
Start From $59.00
 
Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran

Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran

  • Caribbean
  • Superb614 reviews4.7

Welcome aboard the “DOLPHIN”! Join us for an breathtaking sunset sail we’ll make sure it will ....

    Free Cancellation
    Start From $59.00
 
 

Deluxe Half-Day Snorkel Sail on Lady Grace Luxury Catamaran

(4.8 of 316 reviews)

Set sail aboard the luxury sailing catamaran Lady Grace to explore the Turks & Caicos Barrier Reef, home to some of the best snorkeling in the world. After exploring this magical underwater world, you will set sail for a relaxing ... More

Free Cancellation
Start From $189.00
 
Deluxe Half-Day Snorkel Sail on Lady Grace Luxury Catamaran Likely to Sell Out

Deluxe Half-Day Snorkel Sail on Lady Grace Luxury Catamaran

  • Caribbean
  • Superb316 reviews4.8

Set sail aboard the luxury sailing catamaran Lady Grace to explore the Turks & Caicos Barrier Reef, ....

    Free Cancellation
    Start From $189.00
 
 

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

(4.8 of 2,073 reviews)

Come swim with the resident green sea turtles and tropical fish on this 3 hour snorkel & sail adventure in St. Thomas aboard The VI Cat. From your departure, set sail on our 54-foot US Coast Guard inspected catamaran to the idylli... More

Free Cancellation
Start From $119.00
 
Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT Likely to Sell Out

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

  • Caribbean
  • Superb2,073 reviews4.8

Come swim with the resident green sea turtles and tropical fish on this 3 hour snorkel & sail advent....

    Free Cancellation
    Start From $119.00
 
 

Aruba Sunset Sail with Appetizers and Open Bar

(4.5 of 2,005 reviews)

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 stars come out. Relax as the friendly crew entertains you with local music, dancing... More

Free Cancellation
Start From $92.00
 
Aruba Sunset Sail with Appetizers and Open Bar Likely to Sell Out

Aruba Sunset Sail with Appetizers and Open Bar

  • Caribbean
  • Exellent2,005 reviews4.5

Experience Aruba's spectacular sunset aboard a luxury catamaran. Enjoy views of Palm Beach from the ....

    Free Cancellation
    Start From $92.00
 
 

Barbados -Luxury Cruise with Lunch and Open Bar By Oceanluxx

(4.8 of 129 reviews)

Discover the pinnacle of luxury aboard Barbados’ newest gem — our 30ft double-decker pontoon boat. Designed for intimate gatherings of up to 15 guests, this exclusive experience combines modern comfort with first-class hospita... More

Free Cancellation
Start From $125.00
 
Barbados -Luxury Cruise with Lunch and Open Bar By Oceanluxx Likely to Sell Out

Barbados -Luxury Cruise with Lunch and Open Bar By Oceanluxx

  • Caribbean
  • Superb129 reviews4.8

Discover the pinnacle of luxury aboard Barbados’ newest gem — our 30ft double-decker pontoon boa....

    Free Cancellation
    Start From $125.00
 
 

2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)

(4.8 of 999 reviews)

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 of Grace Bay in Providenciales, sailing for two hours over crystalline waters aboard a spaci... More

Free Cancellation
Start From $121.53
 
2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only) Likely to Sell Out

2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Ad....

  • Caribbean
  • Superb999 reviews4.8

There’s no better way to see the setting Caribbean sun than with a Champagne Sail in Turks and Cai....

    Free Cancellation
    Start From $121.53
 
 

Jost Van Dyke, Sandy Spit and White bay sailing tour in the BVI

(5 of 19 reviews)

***Ideal for Cruise Ship Guests-Taxi included*** If staying in a hotel/villa, please book our other Jost Van Dyke listing first. You can book this shared sail if the other option is not available. Welcome aboard, fellow adventur... More

Free Cancellation
Start From $218.00
 
Jost Van Dyke, Sandy Spit and White bay sailing tour in the BVI Likely to Sell Out

Jost Van Dyke, Sandy Spit and White bay sailing tour in the BVI

  • Caribbean
  • Superb19 reviews5

***Ideal for Cruise Ship Guests-Taxi included*** If staying in a hotel/villa, please book our other....

    Free Cancellation
    Start From $218.00
 
 

Arusun Catamaran Sail with Snorkeling in Aruba

(4.8 of 2,374 reviews)

Have a warm Aruban welcome on board of a beautiful 65-foot catamaran, the Arusun, and spend the most fun, relaxing 2.5 hours exploring the Caribbean Sea. There is no better way to explore the marine life of Aruba then on this extr... More

Free Cancellation
Start From $63.00
 
Arusun Catamaran Sail with Snorkeling in Aruba Likely to Sell Out

Arusun Catamaran Sail with Snorkeling in Aruba

  • Caribbean
  • Superb2,374 reviews4.8

Have a warm Aruban welcome on board of a beautiful 65-foot catamaran, the Arusun, and spend the most....

    Free Cancellation
    Start From $63.00
 
 

Aruba Sunset Cruise plus Seaside Dinner

(4.4 of 946 reviews)

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 open bar while you enjoy the famous Caribbean sunset. After two hours on the wat... More

Free Cancellation
Start From $122.00
 
Aruba Sunset Cruise plus Seaside Dinner Likely to Sell Out

Aruba Sunset Cruise plus Seaside Dinner

  • Caribbean
  • Exellent946 reviews4.4

Spend a relaxing evening in Aruba on a sunset cruise followed by a waterfront seafood dinner. Sail a....

    Free Cancellation
    Start From $122.00
 
 

Snorkel Cat All Inclusive Adventure

(4.9 of 780 reviews)

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 island—all in one all-inclusive excursion. We provide breakfast, lunch, drinks, an... More

Free Cancellation
Start From $175.00
 
Snorkel Cat All Inclusive Adventure Likely to Sell Out

Snorkel Cat All Inclusive Adventure

  • Caribbean
  • Superb780 reviews4.9

What makes our trip unique is the rare opportunity to snorkel at both the pristine waters of St. Joh....

    Free Cancellation
    Start From $175.00
 
 

Aruba Morning Snorkel Sail & Champagne Brunch

(4.7 of 2,017 reviews)

Start your day on a high note by embarking on a catamaran cruise across the turquoise waters of Aruba. Indulge in a mimosa brunch experience on board while you cruise to three snorkeling spots, where you’ll swim in the clear Car... More

Free Cancellation
Start From $85.00
 
Aruba Morning Snorkel Sail & Champagne Brunch Likely to Sell Out

Aruba Morning Snorkel Sail & Champagne Brunch

  • Caribbean
  • Superb2,017 reviews4.7

Start your day on a high note by embarking on a catamaran cruise across the turquoise waters of Arub....

    Free Cancellation
    Start From $85.00
 
 

Small-Group Cruising and Snorkeling Catamaran Tour

(4.9 of 2,371 reviews)

This small-group sailing and snorkeling catamaran tour is limited to 16 guests per tour; this limited size sets this tour apart from others. With us, you will receive personalized attention. Go swimming in a natural reserve, snork... More

Free Cancellation
Start From $99.00
 
Small-Group Cruising and Snorkeling Catamaran Tour Likely to Sell Out

Small-Group Cruising and Snorkeling Catamaran Tour

  • Caribbean
  • Superb2,371 reviews4.9

This small-group sailing and snorkeling catamaran tour is limited to 16 guests per tour; this limite....

    Free Cancellation
    Start From $99.00
 
 

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

(4.8 of 281 reviews)

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 Lime Out, the only floating taco bar in the Virgin Islands and listed on Time magazine’s 2019 li... More

Free Cancellation
Start From $179.00
 
St. John Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin Likely to Sell Out

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

  • Caribbean
  • Superb281 reviews4.8

Join us for a day of sailing and snorkeling aboard one of our luxury catamarans and enjoy a sun-fill....

    Free Cancellation
    Start From $179.00
 
 

Sunset Sail to Boca Catalina with BBQ Dinner

(4.6 of 256 reviews)

This will have 2 hours of Real Sailing with over 4 sails. We are the longest Sailing trip in Aruba at 4.5 hours instead of 2.5 hours. Lunch or dinner is included.... More

Free Cancellation
Start From $119.00
 
Sunset Sail to Boca Catalina with BBQ Dinner Likely to Sell Out

Sunset Sail to Boca Catalina with BBQ Dinner

  • Caribbean
  • Superb256 reviews4.6

This will have 2 hours of Real Sailing with over 4 sails. We are the longest Sailing trip in Aruba a....

    Free Cancellation
    Start From $119.00
 
 

St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max

(4.9 of 624 reviews)

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 end to what you can see while sailing with Virgin Islands Day Sailing. Join us as we e... More

Free Cancellation
Start From $245.00
 
St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max Likely to Sell Out

St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max

  • Caribbean
  • Superb624 reviews4.9

An Unforgettable Sailing Experience! We offer a Semi-private and all inclusive Day trip that will be....

    Free Cancellation
    Start From $245.00
 
1 2 3 4 5
Booking.com
Booking.com
Booking.com