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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 48 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 $114.99

Grand Cayman Catamaran Dinner Cruise

5 star rating: Highly Recommended 14 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: Georgetown, Cayman Islands
Duration: 3 hours 30 minutes (approx.)

From USD $79.99

Catalina Bay and Antilla Ship Wreck Snorkel Cruise

5 star rating: Highly Recommended 18 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: Oranjestad, Aruba
Duration: 3 hours (approx.)

From USD $48.99

St. Maarten 12 Metre Challenge

5 star rating: Highly Recommended 8 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

Tall Ship Sunset Cruise

4.5 star rating: Recommended 22 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

Anguilla Day Trip from St. Martin

5 star rating: Highly Recommended 38 Reviews

No trip to St. Martin is complete without a day trip to the gorgeous and unspoiled island of sun and sand - Anguilla. You'll cruise to the island by catamaran, ...  Read more

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

From USD $113.99

Small-Group Day Sail in St Maarten

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 $98.10
$108.99 Save $10.89

Nassau Sailing Adventure with Optional Sailing Lesson

4 star rating: Recommended 13 Reviews

Experience the beautiful Caribbean Sea on a sailboat! On this Nassau sailing adventure, learn how to sail from your expert instructor before heading out to ...  Read more

Location: Nassau, Bahamas
Duration: 3 hours (approx.)

From USD $39.99

St Maarten Catamaran Snorkel Sail

5 star rating: Highly Recommended 12 Reviews

Set sail for a full day at sea in St Maarten You'll spend a leisurely day in true Caribbean style, relaxing on a deserted island, going for a snorkel and ...  Read more

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

From USD $118.99

St. Martin Pirates Day Cruise

4.5 star rating: Recommended 10 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 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

Champagne Sunset Cruise in St Maarten

Experience the romance of a Caribbean sunset on a Champagne cruise in St Maarten. While you sail along the coast on a luxury catamaran, enjoy Champagne and ...  Read more

Location: St Maarten (St Martin)
Duration: 2 hours (approx.)

From USD $44.99

Happy Hour Sail and Snorkel in Aruba with Optional Snuba

5 star rating: Highly Recommended 9 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: Oranjestad, Aruba
Duration: 3 hours (approx.)

From USD $64.99

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

Palm Pleasure Sunset Sail

5 star rating: Highly Recommended 12 Reviews

As you sail along Aruba's scenic coastline, enjoy a storybook sunset that sets the scene for romance and fun.

Location: Oranjestad, Aruba
Duration: 2 hours (approx.)

From USD $62.99

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

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