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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Anguilla Day Trip from St Maarten

5 star rating: Highly Recommended 45 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

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

5 star rating: Highly Recommended 50 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

Aruba Palm Pleasure Snorkel Adventure

4.5 star rating: Recommended 14 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

St. Maarten 12 Metre Challenge

5 star rating: Highly Recommended 14 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 $104.99

Grand Cayman Catamaran Dinner Cruise

5 star rating: Highly Recommended 19 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

St Thomas Snorkel and Sail Adventure to St John

5 star rating: Highly Recommended 4 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

Small-Group Day Sail in St Maarten

5 star rating: Highly Recommended 6 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

Barbados Catamaran Snorkeling Cruise

4.5 star rating: Recommended 4 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

Tall Ship Sunset Cruise

4.5 star rating: Recommended 24 Reviews

See the sun set over the magical waters of the Caribbean! Sip on a glass of champagne while the sun sets a romantic back drop taking you into an evening of ...  Read more

Location: Philipsburg, St Maarten
Duration: 2 hours 30 minutes (approx.)

From USD $62.99

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

Catalina Bay and Antilla Shipwreck Snorkel Cruise

4.5 star rating: Recommended 24 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. Martin Pirates Day Cruise

4.5 star rating: Recommended 12 Reviews

Sail a tall ship on crystal clear Caribbean waters, hear exciting tales from the high seas and feel like a real pirate for a day! Spend an exciting and crazy ...  Read more

Location: Philipsburg, St Maarten
Duration: 3 hours (approx.)

From USD $78.99

Happy Hour Sail and Snorkel in Aruba with Optional Snuba

4.5 star rating: Recommended 11 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

San Juan Small-Group Sailing Cruise

5 star rating: Highly Recommended 6 Reviews

Sail on San Juan Bay and enjoy views of the colorful Caribbean as you recline on deck during a two-hour cruise! Sip complimentary drinks and taste fresh ...  Read more

Location: San Juan, Puerto Rico
Duration: 2 hours (approx.)

From USD $121.99

Palm Pleasure Sunset Sail

5 star rating: Highly Recommended 13 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

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

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