Caribbean Sailing Trips

Caribbean Sailing Trips

Cruises, Sailing & Water Tours See all

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Anguilla Day Trip from St Maarten Including Lunch

5 star rating: Highly Recommended 61 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 ...  Read more

Location: Simpson Bay, St Maarten
Duration: 8 hours

From USD $120.00

St Thomas Snorkel and Sail Adventure to St John

5 star rating: Highly Recommended 32 Reviews

Set sail for the snorkel-perfect waters of St John on this fun 6-hour snorkel and sail adventure from St Thomas. Enjoy the warm breezes as you sail into ...  Read more

Location: St. Thomas, US Virgin Islands
Duration: 6 hours

From USD $94.99

7-Day Sailing in the British Virgin Islands

Ever dream of sailing in Caribbean waters? Whether you're taking a flotilla holiday for the first time or you're an experienced sailor, island hopping in the ...  Read more

Location: Tortola, British Virgin Islands
Duration: 8 days

From USD $1,824.42

Private Sailing Charter in St Kitts

5 star rating: Highly Recommended 6 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 ...  Read more

Location: Basseterre, St Kitts
Duration: Flexible

From USD $650.00

Happy Hour Sail and Snorkel in Aruba with Optional Snuba

4.5 star rating: Recommended 29 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 ...  Read more

Location: Aruba
Duration: 3 hours

From USD $65.99

Morning Pirate Sail and Snorkel Cruise in Aruba

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 ...  Read more

Location: Aruba
Duration: 4 hours

From USD $62.10

Nassau Sail and Snorkel Tour

4.5 star rating: Recommended 12 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 ...  Read more

Location: Nassau, Bahamas
Duration: 3 hours

From USD $54.00

St. Maarten 12 Metre Challenge

5 star rating: Highly Recommended 21 Reviews

Ever dreamed of sailing a real racing yacht? Well don't miss out on this fantastic opportunity to race in the warm blue waters and brisk trade winds of the ...  Read more

Location: Philipsburg, St Maarten
Duration: 2.5 - 3 hours

From USD $95.00

St Maarten Sailing and Snorkeling to St Barts

5 star rating: Highly Recommended 2 Reviews

Cruise to St. Barts on a sailing, snorkeling, and sightseeing tour that departs from Dock Maarten. Stops include Île Fourchue, Gustavia, and Colombier on ...  Read more

Location: Sint Maarten, Netherlands
Duration: 9 hours

From USD $139.00

Afternoon Pirate Sail and Snorkel Cruise in Aruba

4.5 star rating: Recommended 3 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, ...  Read more

Location: Oranjestad, Aruba
Duration: 3 hours

From USD $45.00

Aruba Palm Pleasure Snorkel Adventure

4.5 star rating: Recommended 27 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 ...  Read more

Location: Aruba
Duration: 4 hours

From USD $88.99

Small-Group Day Sail in St Maarten

5 star rating: Highly Recommended 13 Reviews

Sail in the Caribbean paradise of St Maarten on a 5-hour cruise including homemade lunch and unlimited drinks from a top shelf open bar. Relax on a cushioned ...  Read more

Location: Simpson Bay, St Maarten
Duration: 5 hours

From USD $108.99

Antigua Shore Excursion: Yacht Racing

5 star rating: Highly Recommended 6 Reviews

If you’re looking for something a little more adrenaline-pumping than snorkeling tours and fishing trips during your Caribbean cruise, don’t miss this ...  Read more

Location: St Johns, Antigua
Duration: 4 hours

From USD $120.00

Palm Pleasure Sunset Sail

4.5 star rating: Recommended 21 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

Sail and Snorkel to Buck Island St Thomas

Sail around the US Virgin Islands on this half-day adventure! Aboard Island Girl enjoy the spectacular sights and sounds of nature away from the crowds on ...  Read more

Location: St Thomas, US Virgin Islands
Duration: 3 hours 30 minutes

From USD $84.00

Cayman Islands Stingray City Luxury Sailing and Swimming Tour

5 star rating: Highly Recommended 1 Review

Sail in the spacious and comfortable Allura catamaran and snorkel in the world famous waters of Grand Cayman’s stingray sandbar.

Location: George Town, Cayman Islands
Duration: 3 hours

From USD $69.99

Day Trip to the Island of Prickly Pear from St Maarten

5 star rating: Highly Recommended 66 Reviews

Any trip to St Maarten would not be complete without a day trip to the gorgeous and unspoiled island of sun and sand - 'Prickly Pear Cay', and a swim ...  Read more

Location: Simpson Bay, St Maarten
Duration: 8 hours

From USD $120.00

Catalina Bay and Antilla Shipwreck Snorkel Cruise

4.5 star rating: Recommended 30 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 ...  Read more

Location: Aruba
Duration: 3 hours

From USD $60.99

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 ...  Read more

Location: Providenciales, Turks and Caicos
Duration: 4 hours

From USD $109.99

Small-Group Sailing and Snorkeling Adventure from Fajardo

Set sail upon the warm Caribbean waters of Puerto Rico in a Beneteau First 39-foot sailboat. In this personalized, small group tour, (limited to 8 passengers) ...  Read more

Location: San Juan, Puerto Rico
Duration: 6 hours

From USD $169.00

St Maarten Sunset Schooner Cruise

4.5 star rating: Recommended 4 Reviews

Enjoy a Caribbean sunset from the water on this St Maarten cruise by historical schooner. On board a sailboat that’s more than 100 years old, ...  Read more

Location: Simpson Bay, St Maarten
Duration: 2 hours

From USD $38.99

St Kitts Snorkel Cruise with Lunch

4 star rating: Recommended 3 Reviews

Sail and snorkel the pristine Caribbean Sea on this great St. Kitts snorkel cruise. Sail past beautiful scenery and island landscape along the coastline ...  Read more

Location: Basseterre, St Kitts
Duration: 3 hours 30 minutes

From USD $97.00

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 ...  Read more

Location: St Johns, Antigua
Duration: 6 hours

From USD $100.00

Old San Juan Harbor Sail

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

Location: San Juan, Puerto Rico
Duration: 90 minutes

From USD $59.00

Grand Cayman Kittiwake and Reef Sail

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 ...  Read more

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

From USD $70.00
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Only Show: Airboat Tours | Brunch Cruises | Catamaran Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Glass Bottom Boat Tours | Gondola Cruises | Lunch Cruises | Multi-day Cruises | Night Cruises | Sailing Trips | Submarine Tours | Sunset Cruises

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