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Top 10 Best Caribbean Sailing Trips

Found 390 Sailing Trips activities in Caribbean. Sort by Popularity. - Page 4
 

Aruba Sunset Sail Dinner Cruise with Open Bar by Catamaran

(4.8 of 393 reviews)

Included in this three (3) hour sail is a dinner buffet with appetizers, mains and dessert buffet and an open bar with sparkling wine (welcome drink), house wine, cocktail menu, local beer and soda's & juices.... More

Free Cancellation
Start From $137.00
 
Aruba Sunset Sail Dinner Cruise with Open Bar by Catamaran

Aruba Sunset Sail Dinner Cruise with Open Bar by Catamaran

  • Caribbean
  • Superb393 reviews4.8

Included in this three (3) hour sail is a dinner buffet with appetizers, mains and dessert buffet an....

    Free Cancellation
    Start From $137.00
 
 

Norman Island - The Caves & The Indians - Sailing & Snorkel Tour

(5 of 19 reviews)

***Ideal for hotel/villa Guests*** If arriving by cruise , please book our other Norman Island listing first. You can book this shared sail if the other option is not available. Welcome aboard, fellow adventurers, to the breatht... More

Free Cancellation
Start From $208.00
 
Norman Island - The Caves & The Indians - Sailing & Snorkel Tour

Norman Island - The Caves & The Indians - Sailing & Snorkel Tour

  • Caribbean
  • Superb19 reviews5

***Ideal for hotel/villa Guests*** If arriving by cruise , please book our other Norman Island list....

    Free Cancellation
    Start From $208.00
 
 

Aruba Sunset Sail with Open Bar

(4.5 of 379 reviews)

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

Free Cancellation
Start From $112.00
 
Aruba Sunset Sail with Open Bar

Aruba Sunset Sail with Open Bar

  • Caribbean
  • Exellent379 reviews4.5

With this trip you will sail along Aruba's scenic coastline and enjoy the most spectacular and fun s....

    Free Cancellation
    Start From $112.00
 
 

Leisure Full Day Catamaran (Blue, Aqua or LIC)

(4.9 of 18 reviews)

Crafted Catamarans: Specifically designed for water tours, comfort, spacious decks, shaded seating areas, bar, and restroom for the enjoyment of passengers. Scenic Coastal Routes: Allowing passengers to enjoy the picturesque coas... More

Free Cancellation
Start From $155.00
 
Leisure Full Day Catamaran (Blue, Aqua or LIC) Likely to Sell Out

Leisure Full Day Catamaran (Blue, Aqua or LIC)

  • Caribbean
  • Superb18 reviews4.9

Crafted Catamarans: Specifically designed for water tours, comfort, spacious decks, shaded seating a....

    Free Cancellation
    Start From $155.00
 
 

Good Times Too Premium Catamaran Lunch Cruise

(4.9 of 215 reviews)

Our Lunch cruise on Good Times Too offers limited numbers of passengers of 20 persons. We start from the west coast (not Bridgetown) with the advantage of arriving at the turtle site before the main crowd. Our crew and staff provi... More

Free Cancellation
Start From $154.00
 
Good Times Too Premium Catamaran Lunch Cruise Likely to Sell Out

Good Times Too Premium Catamaran Lunch Cruise

  • Caribbean
  • Superb215 reviews4.9

Our Lunch cruise on Good Times Too offers limited numbers of passengers of 20 persons. We start from....

    Free Cancellation
    Start From $154.00
 
 

Tropical Catamaran Snorkeling, Sailing And Beach Experience

(4.8 of 285 reviews)

Join us for a 6 Hours yachting, sailing, and snorkeling experience. Your comfort and safety are our main concern. We will do an easy South side Coastal sailing French Side, Dutch Side with 2 or more stops for snorkeling, beach t... More

Free Cancellation
Start From $132.08
 
Tropical Catamaran Snorkeling, Sailing And Beach Experience Likely to Sell Out

Tropical Catamaran Snorkeling, Sailing And Beach Experience

  • Caribbean
  • Superb285 reviews4.8

Join us for a 6 Hours yachting, sailing, and snorkeling experience. Your comfort and safety are ou....

    Free Cancellation
    Start From $132.08
 
 

3 hour Glow Worm Sunset Cruise from Providenciales

(4.6 of 148 reviews)

Watch the bioluminescence of glow worms on a spectacular sunset cruise from Providenciales! For a few evenings after the full moon each month, the waters of Caicos Banks play host to this natural phenomenon, when thousands of glow... More

Free Cancellation
Start From $133.69
 
3 hour Glow Worm Sunset Cruise from Providenciales Likely to Sell Out

3 hour Glow Worm Sunset Cruise from Providenciales

  • Caribbean
  • Superb148 reviews4.6

Watch the bioluminescence of glow worms on a spectacular sunset cruise from Providenciales! For a fe....

    Free Cancellation
    Start From $133.69
 
 

Iconic Aruba Sail and Snorkel Experience

(4.8 of 430 reviews)

Experience the joy of sailing along Aruba’s stunning beaches on a spacious catamaran & snorkeling at the marine sanctuary, Catalina bay, and the famous Antilla shipwreck. This tour is not only highly rated, but is also recogniz... More

Free Cancellation
Start From $65.00
 
Iconic Aruba Sail and Snorkel Experience Likely to Sell Out

Iconic Aruba Sail and Snorkel Experience

  • Caribbean
  • Superb430 reviews4.8

Experience the joy of sailing along Aruba’s stunning beaches on a spacious catamaran & snorkelingÂ....

    Free Cancellation
    Start From $65.00
 
 

Sunset & Champagne Cruise on a Classic Schooner with boat dogs

(4.8 of 167 reviews)

...the perfect ending to another perfect day. Sail just offshore of the coast of Grenada. Enjoy a glass of champagne, fresh Appetizers from the onboard chef and cold drinks from our open bar while taking in the remarkable view of... More

Free Cancellation
Start From $85.00
 
Sunset & Champagne Cruise on a Classic Schooner with boat dogs Likely to Sell Out

Sunset & Champagne Cruise on a Classic Schooner with boat dogs

  • Caribbean
  • Superb167 reviews4.8

...the perfect ending to another perfect day. Sail just offshore of the coast of Grenada. Enjoy a g....

    Free Cancellation
    Start From $85.00
 
 

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

(4.9 of 637 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
  • Superb637 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
 
 

Punta Cana Private Catamaran Cruise: Snorkeling, Beach & BBQ

(4.6 of 39 reviews)

This private catamaran tour in Punta Cana combines adventure, relaxation, and VIP exclusivity in one unforgettable experience. Unlike shared tours, this all-inclusive cruise is reserved just for your group—giving you full access... More

Free Cancellation
Private Tour
Start From $595.00
 
Punta Cana Private Catamaran Cruise: Snorkeling, Beach & BBQ Likely to Sell Out

Punta Cana Private Catamaran Cruise: Snorkeling, Beach & BBQ

  • Caribbean
  • Superb39 reviews4.6

This private catamaran tour in Punta Cana combines adventure, relaxation, and VIP exclusivity in one....

    Free Cancellation
    Private Tour
    Start From $595.00
 
 

Restless Native Catamaran Sail and Snorkel Tour

(4.9 of 940 reviews)

Get the most out of your time in Bermuda with a 3.5-hour sail on a pink catamaran. Your captain makes for a fun guide as he regales you with intriguing historical anecdotes about the island. Spend about an hour sailing around Berm... More

Free Cancellation
Private Tour
Start From $95.00
 
Restless Native Catamaran Sail and Snorkel Tour Likely to Sell Out

Restless Native Catamaran Sail and Snorkel Tour

  • Caribbean
  • Superb940 reviews4.9

Get the most out of your time in Bermuda with a 3.5-hour sail on a pink catamaran. Your captain make....

    Free Cancellation
    Private Tour
    Start From $95.00
 
 

Hakuna Matata - St Maarten Catamaran day cruise

(4.7 of 79 reviews)

Enjoy a relaxed day perfect for families (kids welcome!), couples, and groups. Captain Robert, with years of experience sailing the world’s oceans, shares captivating stories above and below the surround water. We pride ourselv... More

Free Cancellation
Private Tour
Start From $169.00
 
Hakuna Matata - St Maarten Catamaran day cruise Likely to Sell Out

Hakuna Matata - St Maarten Catamaran day cruise

  • Caribbean
  • Superb79 reviews4.7

Enjoy a relaxed day perfect for families (kids welcome!), couples, and groups. Captain Robert, with ....

    Free Cancellation
    Private Tour
    Start From $169.00
 
 

Chill and Grill Catamaran Tour in Bonaire

(5 of 573 reviews)

With our Catamaran, we will sail along the beautiful coast of Bonaire and Klein Bonaire. We will stop for our first snorkel experience somewhere in the Bonaire Marine Park, our professional guide will lead you into the water to di... More

Free Cancellation
Private Tour
Start From $135.00
 
Chill and Grill Catamaran Tour in Bonaire Likely to Sell Out

Chill and Grill Catamaran Tour in Bonaire

  • Caribbean
  • Superb573 reviews5

With our Catamaran, we will sail along the beautiful coast of Bonaire and Klein Bonaire. We will sto....

    Free Cancellation
    Private Tour
    Start From $135.00
 
 

Two islands, One paradise

(5 of 5 reviews)

Sailing between St Kitts and Nevis is a totally unique experience. The trade winds constantly blow, and our route along the leeward side of St Kitts gives us flat water and constant breeze, Ideal sailing conditions. Come and see t... More

Free Cancellation
Private Tour
Start From $125.00
 
Two islands, One paradise Likely to Sell Out

Two islands, One paradise

  • Caribbean
  • Superb5 reviews5

Sailing between St Kitts and Nevis is a totally unique experience. The trade winds constantly blow, ....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Luxury Lagoon Cruise with Onboard Chef and Signature Cocktails

(4.8 of 243 reviews)

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 cool refreshment or lay down on one of our lounges to unwind and take in the sight. So... More

Free Cancellation
Private Tour
Start From $149.00
 
Luxury Lagoon Cruise with Onboard Chef and Signature Cocktails Likely to Sell Out

Luxury Lagoon Cruise with Onboard Chef and Signature Cocktails

  • Caribbean
  • Superb243 reviews4.8

The Luxury Lagoon Cruise allows you to cruise along Aruba’s Southern Coast aboard our Teak Schoone....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Days End Sunset Sail from the Westin at Frenchman's Reef

(4.6 of 34 reviews)

Step aboard the Flying Frenchman, our newly designed, state-of-the-art, luxury sailing catamaran for a fun and relaxing sunset sail departing from Frenchman’s Reef. Take in a magnificent Caribbean sunset while under sail and enj... More

Free Cancellation
Private Tour
Start From $99.00
 
Days End Sunset Sail from the Westin at Frenchman's Reef Likely to Sell Out

Days End Sunset Sail from the Westin at Frenchman's Reef

  • Caribbean
  • Superb34 reviews4.6

Step aboard the Flying Frenchman, our newly designed, state-of-the-art, luxury sailing catamaran for....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Private Angelfish Snorkeling with Brunch in Aruba

(5 of 2 reviews)

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 Sailing will provide you with the memory of a lifetime! This boat charter is pri... More

Free Cancellation
Private Tour
Start From $50.50
 
Private Angelfish Snorkeling with Brunch in Aruba Likely to Sell Out

Private Angelfish Snorkeling with Brunch in Aruba

  • Caribbean
  • Superb2 reviews5

You are cordially invited to indulge yourself in the privacy and comfort of an Aruba sailing charter....

    Free Cancellation
    Private Tour
    Start From $50.50
 
 

Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)

(5 of 139 reviews)

The Virgin Islands are the sailing capital of the world!! Sail with us from St. Thomas to the exotic island of Jost Van Dyke. This trip is limited to only 12 guests. A light continental Breakfast and a full open bar w/bottomless... More

Free Cancellation
Private Tour
Start From $375.00
 
Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar) Likely to Sell Out

Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)

  • Caribbean
  • Superb139 reviews5

The Virgin Islands are the sailing capital of the world!! Sail with us from St. Thomas to the exotic....

    Free Cancellation
    Private Tour
    Start From $375.00
 
 

Small Group Snorkeling, Sharks & Rays Encounter At Punta Cana

(4 of 82 reviews)

Spend an unforgettable day on the water with this 3-hour by small boat and reef adventure from Punta Cana. Get up close and personal with the Caribbean’s rich marine life without having to get wet. Marvel at gorgeous schools of ... More

Free Cancellation
Private Tour
Start From $99.99
 
Small Group Snorkeling, Sharks & Rays Encounter At Punta Cana Likely to Sell Out

Small Group Snorkeling, Sharks & Rays Encounter At Punta Cana

  • Caribbean
  • Very Good82 reviews4

Spend an unforgettable day on the water with this 3-hour by small boat and reef adventure from Punta....

    Free Cancellation
    Private Tour
    Start From $99.99
 
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