Caribbean Sailing Trips

Caribbean Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: Day Cruises | Dolphin & Whale Watching | Night Cruises | Sailing Trips | Submarine Tours

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Bermuda Catamaran Sail and Snorkel Tour

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 ...  Read more

Location: Bermuda
Duration: 3 hours 30 minutes (approx.)

From USD $64.99

Catamaran Cruise with Snorkeling, Paddleboarding and Kayaking

5 star rating: Highly Recommended 12 Reviews

Spend an afternoon on the water during this Bermuda catamaran and snorkeling cruise. Feel the sea breeze on your face as you sail through Bermuda’s turquoise ...  Read more

Location: Bermuda
Duration: 3 hours (approx.)

From USD $68.99

Day Trip to the Island of Prickly Pear from St. Martin

5 star rating: Highly Recommended 53 Reviews

Any trip to St. Martin would not be complete without a day trip to the gorgeous and unspoiled island of sun and sand - 'Anguilla', and her unparalleled sister ...  Read more

Location: Simpson Bay, St Maarten
Duration: 8 hours (approx.)

From USD $109.99

Anguilla Day Trip from St Maarten

5 star rating: Highly Recommended 49 Reviews

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

Location: Simpson Bay, St Maarten
Duration: 8 hours (approx.)

From USD $113.99

Grand Cayman Catamaran Dinner Cruise

4.5 star rating: Recommended 24 Reviews

Dine under the stars with your loved one on this romantic Grand Cayman dinner cruise. Sail from Seven Mile Beach aboard a luxury catamaran and take in gorgeous ...  Read more

Location: George Town, Grand Cayman
Duration: 3 hours 30 minutes (approx.)

From USD $79.99

Catalina Bay and Antilla Shipwreck Snorkel Cruise

4.5 star rating: Recommended 25 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 ...  Read more

Location: Aruba
Duration: 3 hours (approx.)

From USD $55.99

St Thomas Snorkel and Sail Adventure to St John

5 star rating: Highly Recommended 7 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 the ...  Read more

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

From USD $94.99

Aruba Palm Pleasure Snorkel Adventure

4.5 star rating: Recommended 18 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, ...  Read more

Location: Aruba
Duration: 4 hours (approx.)

From USD $89.99

Happy Hour Sail and Snorkel in Aruba with Optional Snuba

4.5 star rating: Recommended 13 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 ...  Read more

Location: Aruba
Duration: 3 hours (approx.)

From USD $66.99

Small-Group Day Sail in St Maarten

5 star rating: Highly Recommended 7 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 (approx.)

From USD $108.99

Catamaran Day Trip to Nevis Including Pinney's Beach

Board your Catamaran for the sailing, snorkeling and relax on the beach on a way you will never forget! Snorkel in a secluded cove, with all equipment ...  Read more

Location: Basseterre, St Kitts
Duration: 7 hours (approx.)

From USD $101.00

Palm Pleasure Sunset Sail

5 star rating: Highly Recommended 15 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 (approx.)

From USD $64.99

Barbados Catamaran Snorkeling Cruise

4.5 star rating: Recommended 10 Reviews

Take a fun and relaxing catamaran cruise along the west coast of Barbados! On board a spacious schooner, sail to two or three different snorkeling spots, where ...  Read more

Location: Barbados
Duration: 3-5 hours

From USD $69.99

Bermuda Sunset Cocktail Cruise

5 star rating: Highly Recommended 3 Reviews

Start a night out in Bermuda the right way with a 1.5-hour sunset cocktail cruise aboard a 50-foot catamaran. Sunsets in paradise are always great, but they’re ...  Read more

Location: Bermuda
Duration: 1 hour 30 minutes (approx.)

From USD $44.99

Sail and Snorkel Tour from Providenciales

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 ...  Read more

Location: Providenciales, Turks and Caicos
Duration: 4 hours (approx.)

From USD $94.99

Only Show: Day Cruises | Dolphin & Whale Watching | Night Cruises | Sailing Trips | Submarine Tours

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