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Top 10 Best Caribbean Sailing Trips

Found 345 Sailing Trips activities in Caribbean. Sort by Popularity. - Page 5
 

Punta Cana Parasailing and Snorkeling Cruise

(4.7 of 550 reviews)

Surprise yourself in this combination of two great excursions. While the clear water splashes your feet, fly 500 feet high and enjoy a spectacular panoramic view of the coast of Punta Cana. Hop on a catamaran cruise with unlimited... More

Free Cancellation
Start From $124.95
 
Punta Cana Parasailing and Snorkeling Cruise

Punta Cana Parasailing and Snorkeling Cruise

  • Caribbean
  • Superb550 reviews4.7

Surprise yourself in this combination of two great excursions. While the clear water splashes your f....

    Free Cancellation
    Start From $124.95
 
 

Punta Cana Combo Tour: Snorkeling, Catamaran Cruise & Parasailing

(4.6 of 1,071 reviews)

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 some time on a doble deck catamaran. Discover the wonders of the sea and enj... More

Free Cancellation
Start From $129.00
 
Punta Cana Combo Tour: Snorkeling, Catamaran Cruise & Parasailing

Punta Cana Combo Tour: Snorkeling, Catamaran Cruise & Parasailing

  • Caribbean
  • Superb1,071 reviews4.6

Enjoy a 500 feet high panoramic view of the entire coastline and turquoise waters of Bavaro Beach th....

    Free Cancellation
    Start From $129.00
 
 

Saona Island, Natural pool Starfish, Fast boat, Catamaran +Dances

(4.7 of 39 reviews)

Saona is a paradise island, part of the National Park of the East. Everyone who was lucky enough to visit Saona notes the incredible turquoise color of the water, white sand and countless palm trees along the coast. You will swim ... More

Free Cancellation
Start From $169.00
 
Saona Island, Natural pool Starfish, Fast boat, Catamaran +Dances

Saona Island, Natural pool Starfish, Fast boat, Catamaran +Dances

  • Caribbean
  • Superb39 reviews4.7

Saona is a paradise island, part of the National Park of the East. Everyone who was lucky enough to ....

    Free Cancellation
    Start From $169.00
 
 

4 Hour Private Catamaran Sail and Snorkel from Grace Bay Beach, Providenciales

(4.9 of 174 reviews)

The discerning visitors choice for over 20 years. The one excursion company that is all about you. This excursion is a genuine sailing adventure, we actually sail. Help us hoist the sails or just sit back, relax and experience t... More

Free Cancellation
Private Tour
Start From $2,380.00
 
4 Hour Private Catamaran Sail and Snorkel from Grace Bay Beach, Providenciales

4 Hour Private Catamaran Sail and Snorkel from Grace Bay Beach, P....

  • Caribbean
  • Superb174 reviews4.9

The discerning visitors choice for over 20 years. The one excursion company that is all about you.....

    Free Cancellation
    Private Tour
    Start From $2,380.00
 
 

Small Group Snorkeling, Sharks & Rays Encounter At Punta Cana

(3.9 of 68 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 $98.00
 
Small Group Snorkeling, Sharks & Rays Encounter At Punta Cana

Small Group Snorkeling, Sharks & Rays Encounter At Punta Cana

  • Caribbean
  • Very Good68 reviews3.9

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 $98.00
 
 

Aruba Sail and Snorkel with Crafted Cocktails

(4.8 of 343 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
Private Tour
Start From $62.00
 
Aruba Sail and Snorkel with Crafted Cocktails

Aruba Sail and Snorkel with Crafted Cocktails

  • Caribbean
  • Superb343 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $62.00
 
 

Private, Skippered Catamaran Day Trip in Grenada

(4.7 of 30 reviews)

With this 7-hour Day Trip, you will enjoy the most beautiful sights of the south coast of Grenada onboard our luxury catamaran. The boat is fully equipped to make sure you can fully enjoy your day with us, whether you want an acti... More

Free Cancellation
Private Tour
Start From $1,155.00
 
Private, Skippered Catamaran Day Trip in Grenada

Private, Skippered Catamaran Day Trip in Grenada

  • Caribbean
  • Superb30 reviews4.7

With this 7-hour Day Trip, you will enjoy the most beautiful sights of the south coast of Grenada on....

    Free Cancellation
    Private Tour
    Start From $1,155.00
 
 

SUNSET PARTY CATAMARAN NEGRIL with transfers from Montego Bay

(4.7 of 30 reviews)

LETS PARTY...!!! This is an ADULTS ONLY Catamaran Cruise, over 18's. When arriving at the departure area of JAMWEST BEACH NEGRIL 7 MILE, the party starts, with DJ's playing and fun and games on the beach are just the start of your... More

Free Cancellation
Private Tour
Start From $140.00
 
SUNSET PARTY CATAMARAN NEGRIL with transfers from Montego Bay

SUNSET PARTY CATAMARAN NEGRIL with transfers from Montego Bay

  • Caribbean
  • Superb30 reviews4.7

LETS PARTY...!!! This is an ADULTS ONLY Catamaran Cruise, over 18's. When arriving at the departure ....

    Free Cancellation
    Private Tour
    Start From $140.00
 
 

Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten

(5 of 276 reviews)

Our Captain has 25+ years of experience, 0 incidents and is super helpful. He loves to tell amazing stories and will keep you entertained with his great energy. Our business is family owned, super friendly, warm and cozy kid frie... More

Free Cancellation
Private Tour
Start From $1,600.00
 
Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten

Private Full-Day Luxury Sailing Catamaran Charter in Sint Maarten

  • Caribbean
  • Superb276 reviews5

Our Captain has 25+ years of experience, 0 incidents and is super helpful. He loves to tell amazing ....

    Free Cancellation
    Private Tour
    Start From $1,600.00
 
 

Maho Bay Turtle Snorkel with Lunch and Bar at Frenchman's Reef

(5 of 1 review)

Embark on a snorkeling adventure to Maho Bay, a pristine paradise known for crystal-clear waters and vibrant marine life. Feel the salty breeze as you make your way to the bay on power catamaran, Jost Boat. The journey is a feast ... More

Free Cancellation
Private Tour
Start From $139.00
 
Maho Bay Turtle Snorkel with Lunch and Bar at Frenchman's Reef Likely to Sell Out

Maho Bay Turtle Snorkel with Lunch and Bar at Frenchman's Reef

  • Caribbean
  • Superb1 review5

Embark on a snorkeling adventure to Maho Bay, a pristine paradise known for crystal-clear waters and....

    Free Cancellation
    Private Tour
    Start From $139.00
 
 

Aruba Afternoon Snorkel Sail aboard Palm Pleasure Catamaran

(4.6 of 266 reviews)

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 snorkeling around the historical Antilla shipwreck, the largest and most fa... More

Free Cancellation
Private Tour
Start From $85.00
 
Aruba Afternoon Snorkel Sail aboard Palm Pleasure Catamaran Likely to Sell Out

Aruba Afternoon Snorkel Sail aboard Palm Pleasure Catamaran

  • Caribbean
  • Superb266 reviews4.6

Experience Aruba's magical marine life as you set sail aboard a spacious catamaran and snorkel at tw....

    Free Cancellation
    Private Tour
    Start From $85.00
 
 

St. John Sail with Bar and Hors d'Oeuvres to Lovango Dinner

(4.5 of 26 reviews)

The private island escape of Lovango Resort + Beach Club is the newest go-to destination in the USVI. Enjoy an unforgettable waterfront meal with breathtaking views looking out over Pillsbury Bay with St. John in the distance, whi... More

Free Cancellation
Private Tour
Start From $119.00
 
St. John Sail with Bar and Hors d'Oeuvres to Lovango Dinner Likely to Sell Out

St. John Sail with Bar and Hors d'Oeuvres to Lovango Dinner

  • Caribbean
  • Exellent26 reviews4.5

The private island escape of Lovango Resort + Beach Club is the newest go-to destination in the USVI....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Good Vibration Catamaran Sail Swim Snorkel

(4.4 of 29 reviews)

Hop aboard Bermuda's newest catamaran, good vibrations, for a fun-filled excursion of cruising, sailing, swimming, lounging and snorkeling along the shoreline. ... More

Free Cancellation
Private Tour
Start From $111.12
 
Good Vibration Catamaran Sail Swim Snorkel Likely to Sell Out

Good Vibration Catamaran Sail Swim Snorkel

  • Caribbean
  • Exellent29 reviews4.4

Hop aboard Bermuda's newest catamaran, good vibrations, for a fun-filled excursion of cruising, sail....

    Free Cancellation
    Private Tour
    Start From $111.12
 
 

Full Day Sail with Max Charters

(5 of 118 reviews)

A day with Max Charters is a unique way to experience the Virgin Islands. We carry fewer passengers than most charter companies in order to provide a more intimate experience. Avoid the crowd and enjoy a relaxing day in the island... More

Free Cancellation
Private Tour
Start From $270.00
 
Full Day Sail with Max Charters Likely to Sell Out

Full Day Sail with Max Charters

  • Caribbean
  • Superb118 reviews5

A day with Max Charters is a unique way to experience the Virgin Islands. We carry fewer passengers ....

    Free Cancellation
    Private Tour
    Start From $270.00
 
 

Enjoy the 100% eco-friendly Sailing Lagoon: Snorkelling Paddle

(5 of 65 reviews)

Perfect for reconnecting with nature, sharing passion in a lagoon where you can take the helm of Ti Bo under sail and develop your maritime culture. Calm body of water protected by the coral reef. Stopovers: swimming snorkelling p... More

Free Cancellation
Private Tour
Start From $96.34
 
Enjoy the 100% eco-friendly Sailing Lagoon: Snorkelling Paddle Likely to Sell Out

Enjoy the 100% eco-friendly Sailing Lagoon: Snorkelling Paddle

  • Caribbean
  • Superb65 reviews5

Perfect for reconnecting with nature, sharing passion in a lagoon where you can take the helm of Ti ....

    Free Cancellation
    Private Tour
    Start From $96.34
 
 

Little Bay Half-Day Sail & Snorkel Adventure

(5 of 36 reviews)

Indulge in an authentic sailing experience on a classic Caribbean "Rum Runner" of yesteryear as Tradition sails to one of Anguilla's hidden treasures, Little Bay.  Home to turtles, nesting pelicans, tropic birds and magnificent... More

Free Cancellation
Private Tour
Start From $254.98
 
Little Bay Half-Day Sail & Snorkel Adventure Likely to Sell Out

Little Bay Half-Day Sail & Snorkel Adventure

  • Caribbean
  • Superb36 reviews5

Indulge in an authentic sailing experience on a classic Caribbean "Rum Runner" of yesteryear as Tra....

    Free Cancellation
    Private Tour
    Start From $254.98
 
 

Knot at Work - Half Day Private Catamaran Cruise in Sint Maarten

(5 of 2 reviews)

Join us on Knot at Work, 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 ... More

Free Cancellation
Private Tour
Start From $770.00
 
Knot at Work - Half Day Private Catamaran Cruise in Sint Maarten Likely to Sell Out

Knot at Work - Half Day Private Catamaran Cruise in Sint Maarten

  • Caribbean
  • Superb2 reviews5

Join us on Knot at Work, one of our luxury sail catamarans for an amazing day on the water. We offer....

    Free Cancellation
    Private Tour
    Start From $770.00
 
 

VIP San Juan: Snorkeling Tour with Turtles with Free Videos

(4.9 of 80 reviews)

Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginner-friendly adventure led by a professional guide in small groups of up to 8, ensuring a personalized and high-quality experience ... More

Free Cancellation
Private Tour
Start From $80.00
 
VIP San Juan: Snorkeling Tour with Turtles with Free Videos Likely to Sell Out

VIP San Juan: Snorkeling Tour with Turtles with Free Videos

  • Caribbean
  • Superb80 reviews4.9

Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginn....

    Free Cancellation
    Private Tour
    Start From $80.00
 
 

Half Day Private Sail and Snorkel Trip to St John

(5 of 50 reviews)

Sail with Liberty guests experience real sailing on our spacious, private catamaran. We sail you to the St John National Park for spectacular snorkeling and beachcombing, followed by snacks, drinks, then more sailing. Captain Ryan... More

Free Cancellation
Private Tour
Start From $165.00
 
Half Day Private Sail and Snorkel Trip to St John Likely to Sell Out

Half Day Private Sail and Snorkel Trip to St John

  • Caribbean
  • Superb50 reviews5

Sail with Liberty guests experience real sailing on our spacious, private catamaran. We sail you to ....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

No1Sxm Sunset Sail Experience in St Maarten

(4.9 of 200 reviews)

Are you ready to go Sailing? TRUE sailing on board of No1Sxm Trimaran: stable, smooth, comfortable. The 2 hour Sailing Experience is pure bliss, with a cocktail and snacks, meeting the sunset, sailing along the St.Maarten Coast. ... More

Free Cancellation
Private Tour
Start From $56.00
 
No1Sxm Sunset Sail Experience in St Maarten Likely to Sell Out

No1Sxm Sunset Sail Experience in St Maarten

  • Caribbean
  • Superb200 reviews4.9

Are you ready to go Sailing? TRUE sailing on board of No1Sxm Trimaran: stable, smooth, comfortable. ....

    Free Cancellation
    Private Tour
    Start From $56.00
 
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