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 43 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: St Maarten (St Martin)
Duration: 8 hours (approx.)

From USD $113.99

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

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

5 star rating: Highly Recommended 49 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: St Maarten (St Martin)
Duration: 8 hours (approx.)

From USD $109.99

Small-Group Day Sail in St Maarten

5 star rating: Highly Recommended 3 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: St Maarten (St Martin)
Duration: 5 hours (approx.)

From USD $108.99

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 $83.99

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

Barbados Catamaran Snorkeling Cruise

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

Private Tour: Barbados Catamaran Snorkeling Cruise

While you’re in paradise, treat yourself to a private catamaran cruise along Barbados’ west coast. Spread out and relax with your family and friends on a ...  Read more

Location: Barbados
Duration: 5 hours (approx.)

From USD $173.99

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: St Maarten (St Martin)
Duration: 3 hours (approx.)

From USD $78.99

St. Maarten 12 Metre Challenge

5 star rating: Highly Recommended 12 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: St Maarten (St Martin)
Duration: 2.5 - 3 hours

From USD $104.99

Happy Hour Sail and Snorkel in Aruba with Optional Snuba

4.5 star rating: Recommended 10 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 $64.99

Catalina Bay and Antilla Ship Wreck Snorkel Cruise

4.5 star rating: Recommended 22 Reviews

Head out to the most famous snorkel spot in Aruba on this 3-hour Catalina Bay and Antilla Ship Wreck Snorkel Cruise! Discover the famous snorkel spot, Antilla ...  Read more

Location: Aruba
Duration: 3 hours (approx.)

From USD $48.99

Tall Ship Sunset Cruise

4.5 star rating: Recommended 23 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: St Maarten (St Martin)
Duration: 2 hours 30 minutes (approx.)

From USD $62.99

San Juan Small-Group Sailing Cruise

5 star rating: Highly Recommended 5 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

St Kitts Snorkel Cruise with Lunch

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 (approx.)

From USD $87.99

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

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