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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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

Anguilla Day Trip from St Maarten

5 star rating: Highly Recommended 48 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

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

4.5 star rating: Recommended 20 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

Barbados Catamaran Snorkeling Cruise

4 star rating: Recommended 5 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

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

Aruba Palm Pleasure Snorkel Adventure

4 star rating: Recommended 15 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 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

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

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

Antigua Shore Excursion: Yacht Racing

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 (approx.)

From USD $99.99

St. Martin Pirates Day Cruise

4.5 star rating: Recommended 13 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

Catamaran Cruise with Snorkeling, Paddleboarding and Kayaking

5 star rating: Highly Recommended 6 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

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

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