Top Caribbean Sailing Trips

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Aruba Palm Pleasure Snorkel Adventure

4.5 star rating: Recommended 37 Reviews

Take in all the pleasures of the sea by enjoying a half-day sail and snorkel experience on a spacious 70-foot long catamaran. Lulled by the rhythm of the sea, ... 

Location: Aruba
Duration: 4 hours

From USD $88.99

Small-Group Day Sail in St Maarten

5 star rating: Highly Recommended 20 Reviews

Sail in the Caribbean paradise of St Maarten on a casual yet upscale cruise within walking distance from the cruise ships! Your day includes real sailing, ... 

Location: Philipsburg, St Maarten
Duration: 5 hours

From USD $108.99

Nassau Sail and Snorkel Tour

4 star rating: Recommended 24 Reviews

Enjoy an afternoon of snorkeling, sailing, and sunning aboard a state of the art catamaran! You'll sail out to one of the Islands most beautiful reefs teeming ... 

Location: Nassau, Bahamas
Duration: 3 hours

From USD $65.00

Afternoon Pirate Sail and Snorkel Cruise in Aruba

5 star rating: Highly Recommended 17 Reviews

Enjoy an afternoon snorkeling cruise in Aruba aboard this 85-foot teak Schooner. Visit three great sites: Malmok Reefs, Boca Catalina and the WWII shipwreck, ... 

Location: Oranjestad, Aruba
Duration: 3 hours

From USD $46.58

Morning Pirate Sail and Snorkel Cruise in Aruba

5 star rating: Highly Recommended 12 Reviews

Sail, snorkel, swim and swing in Aruba aboard an impressive 85-foot teak Schooner.  Snorkel and Swim at three sites: You will have the opportunity to visit two ... 

Location: Aruba
Duration: 4 hours

From USD $62.50

Sail and Snorkel Tour from Providenciales

5 star rating: Highly Recommended 2 Reviews

Set sail for a relaxing Caribbean journey on this half-day cruise and snorkeling excursion from Providenciales. Hop aboard a world-class catamaran, operated by ... 

Location: Providenciales, Turks and Caicos
Duration: 4 hours

From USD $123.20

Happy Hour Sail and Snorkel in Aruba with Optional Snuba

4.5 star rating: Recommended 35 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 ... 

Location: Aruba
Duration: 3 hours

From USD $65.99

Old San Juan Harbor Sail

5 star rating: Highly Recommended 5 Reviews

Set sail on a 19th-century style schooner for a journey through time, taking in more than 500 years of history. Uncover the beauty of Old San Juan, El Morro, ... 

Location: San Juan, Puerto Rico
Duration: 90 minutes

From USD $59.00

Curacao Half-Day Snorkel and Luncheon Sail

5 star rating: Highly Recommended 8 Reviews

You haven't seen Curaçao until you've viewed it while sailing along the coast on the Jonalisa ! This excursion brings you to two of the islands' top ... 

Location: Jan Thiel, Curacao
Duration: 4 hours 18 minutes

From USD $75.00

Lunch and Snorkel Sail in Barbados

4.5 star rating: Recommended 26 Reviews

Snorkel over shipwrecks in Carlisle Bay and swim with sea turtles in Payne’s Bay on this lunch cruise in Barbados. Hop aboard the ‘Jolly Roger’ schooner for ... 

Location: Barbados
Duration: 4 hours

From USD $87.00

Palm Pleasure Sunset Sail

5 star rating: Highly Recommended 26 Reviews

As you sail along Aruba's scenic coastline, enjoy a storybook sunset that sets the scene for romance and fun.

Location: Aruba
Duration: 2 hours

From USD $63.99

Private Sailing Charter in St Kitts

5 star rating: Highly Recommended 16 Reviews

Your journey starts with a glass of champagne as you step aboard “Minerva” a 50-foot sailing yacht for your private charter. Lets the staff pamper you as you ... 

Location: Basseterre, St Kitts
Duration: Flexible

From USD $750.00

Aruba Happy Hour Sunset Sail with Food and Drinks

5 star rating: Highly Recommended 1 Review

Experience a wonderful afternoon sailing on the Aruba blue sea and admire the stunning sunset from a 41 ft trimaran sailboat. Board in a fun and relaxing ... 

Location: Noord, Aruba
Duration: 2 hours

From USD $49.99

Private Half Day Sail and Snorkel

The locals and visitors choice for over 18 years and the one excursion company that is all about you. Come and experience the magic aboard our custom day ... 

Location: Grace Bay, Turks and Caicos Islands
Duration: 4 hours

From USD $1,512.00

Anguilla Day Trip from St Maarten Including Lunch

5 star rating: Highly Recommended 73 Reviews

Discover the paradise beaches of Anguilla on this full-day trip from St Maarten. Sail aboard a catamaran and stop at Prickly Pear Island, one of Anguilla’s ... 

Location: Simpson Bay, St Maarten
Duration: 8 hours

From USD $120.00

Grand Cayman Kittiwake and Reef Sail

4.5 star rating: Recommended 2 Reviews

Take a relaxing cruise along the picturesque shores of Seven Mile Beach and enjoy some of the best snorkeling on Grand Cayman! Visit both a wreck and a reef on ... 

Location: George Town, Cayman Islands
Duration: 2 hours 30 minutes

From USD $70.00

San Juan Bay Day Sail

5 star rating: Highly Recommended 10 Reviews

Discover San Juan, Puerto Rico aboard a 30-foot sailboat. Take in the panoramic views on this pleasure sightseeing tour of San Juan Bay and adjacent waters. ... 

Location: San Juan, Puerto Rico
Duration: 90 minutes

From USD $70.00

Catalina Bay and Antilla Shipwreck Snorkel Cruise

4.5 star rating: Recommended 34 Reviews

Sun, sailing and snorkeling — the perfect way to spend an afternoon in Aruba. On this 3-hour tour, cruise the Caribbean waters aboard a catamaran and kick your ... 

Location: Aruba
Duration: 3 hours

From USD $61.08

Aruba Afternoon Snorkeling Tour

5 star rating: Highly Recommended 11 Reviews

Enjoy your Caribbean adventure to the fullest on this 3-hour snorkel cruise from Aruba's Hadicurari Pier. Snorkel in the clear, calm waters of Boca Catalina to ... 

Location: Aruba
Duration: 3 hours

From USD $45.00

Discover Afternoon Snorkel Sail with Open Bar and Snacks

Join in on the Discover Afternoon Tour onboard the 110ft sailboat "Lady Black". We start our afternoon gliding along The Palm Beach Coast while ... 

Location: Oranjestad, Aruba
Duration: 3 hours

From USD $42.00

Sail and Snorkel in Cades Reef

Enjoy the majestic views as you travel down the southern coast of the island. A stop will be made at Cades Reef for the opportunity to snorkel in Antigua's ... 

Location: St Johns, Antigua
Duration: 6 hours

From USD $100.00

Sail and Snorkel the Caicos Cays on the Good Ship Atabeyra

This 4.5 hour excursion takes you out to the Barrier Reef for snorkeling, followed by casual cruising up the Caicos Cay chain as far as Ft. George Cay. Desert ... 

Location: Cockburn Town, Turks and Caicos Islands
Duration: 4 hours 30 minutes

From USD $95.00

St Lucia Sailing Tour on Rodney Bay

Put your Caribbean vacation to good use by learning the basics of sailing on this half-day tour. Out on the waters of Rodney Bay with a highly trained crew, ... 

Location: St Lucia
Duration: 3 hours

From USD $110.00

Punta Cana Pirate Ship Snorkeling Sail

5 star rating: Highly Recommended 1 Review

You are welcomed by our pirate crew aboard the mighty pirate ship ¨Hispaniola¨. As soon as the ship set sails, our new pirates’ recruits, will receive the ... 

Location: Punta Cana, Dominican Republic
Duration: 3 hours

From USD $114.00

Aruba Caribbean Dinner Sail

Step aboard of a luxury catamaran while a steel drum player is playing Caribbean tunes. Sail around the turquoise waters off the coast of Aruba to a wonderful ... 

Location: Oranjestad, Aruba
Duration: 2 hours 30 minutes

From USD $77.65
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