Caribbean Sailing Trips

Caribbean Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: Airboat Tours | Brunch Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Glass Bottom Boat Tours | Gondola Cruises | Lunch Cruises | Multi-day Cruises | Night Cruises | Sailing Trips | Submarine Tours | Sunset Cruises

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Bermuda Catamaran Sail and Snorkel Tour

5 star rating: Highly Recommended 36 Reviews

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

From USD $64.99

Catamaran Cruise with Snorkeling, Paddleboarding and Kayaking

5 star rating: Highly Recommended 29 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 ...  Read more

Location: Bermuda
Duration: 3 hours

From USD $74.99

St Thomas Snorkel and Sail Adventure to St John

5 star rating: Highly Recommended 29 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 ...  Read more

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

From USD $94.99

Bermuda Sunset Cocktail Cruise

5 star rating: Highly Recommended 23 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 ...  Read more

Location: Bermuda
Duration: 90 minutes

From USD $44.99

Punta Cana Small-Group Sailing and Snorkeling Catamaran Tour

5 star rating: Highly Recommended 11 Reviews

This small-group sailing and snorkeling catamaran tour is limited to 16 guests so you can receive personalized attention. Go swimming in a natural reserve, ...  Read more

Location: Punta Cana, Dominican Republic
Duration: 3 hours 30 minutes

From USD $79.00

Day Trip to the Island of Prickly Pear from St Maarten

5 star rating: Highly Recommended 65 Reviews

Any trip to St Maarten would not be complete without a day trip to the gorgeous and unspoiled island of sun and sand - 'Prickly Pear Cay', and a swim ...  Read more

Location: Simpson Bay, St Maarten
Duration: 8 hours

From USD $120.00

St Kitts Deluxe Catamaran Snorkeling Tour With Lunch

5 star rating: Highly Recommended 22 Reviews

Join in on this 4-hour tour and travel on a luxurious catamaran across the turquoise waters of St Kitts & Nevis. Explore the finest snorkeling spot in the ...  Read more

Location: Basseterre, St Kitts
Duration: 4 hours

From USD $69.99

Anguilla Day Trip from St Maarten Including Lunch

5 star rating: Highly Recommended 59 Reviews

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

Location: Simpson Bay, St Maarten
Duration: 8 hours

From USD $120.00

Nassau Sail and Snorkel Tour

4 star rating: Recommended 10 Reviews

Enjoy an afternoon of snorkeling, sailing, and sunning aboard a state of the art catamaran! You'll sail out to one of the Islands most beautiful reefs ...  Read more

Location: Nassau, Bahamas
Duration: 3 hours

From USD $54.00

Happy Hour Sail and Snorkel in Aruba with Optional Snuba

4.5 star rating: Recommended 27 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 ...  Read more

Location: Aruba
Duration: 3 hours

From USD $65.99

Catamaran and Snorkel Tour of Punta Cana

5 star rating: Highly Recommended 5 Reviews

Step aboard Dream Sail, a luxury catamaran for a 4 hour, exhilarating cruise along the Bavaro Beach, which is considered a natural treasure by the Dominican ...  Read more

Location: Punta Cana, Dominican Republic
Duration: 3 hours

From USD $59.00

Morning Pirate Sail and Snorkel Cruise in Aruba

Sail, snorkel, swim and swing in Aruba aboard an impressive 85-foot teak Schooner.  Snorkel and Swim at three sites: You will have the opportunity to visit two ...  Read more

Location: Aruba
Duration: 4 hours

From USD $62.10

Barbados Catamaran Snorkeling Cruise

5 star rating: Highly Recommended 30 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, ...  Read more

Location: Barbados
Duration: 3-5 hours

From USD $69.99

Small-Group Day Sail in St Maarten

5 star rating: Highly Recommended 13 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 ...  Read more

Location: Simpson Bay, St Maarten
Duration: 5 hours

From USD $108.99

Aruba Palm Pleasure Snorkel Adventure

4.5 star rating: Recommended 27 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 ...  Read more

Location: Aruba
Duration: 4 hours

From USD $88.99

St Kitts Full Day Catamaran to Nevis

5 star rating: Highly Recommended 2 Reviews

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

Location: Basseterre, St Kitts
Duration: 7 hours

From USD $99.99

Private Sailing Charter in St Kitts

5 star rating: Highly Recommended 3 Reviews

Your journey starts with a glass of champagne as you step aboard “Minerva” a 50-foot sailing yacht for your private charter. Lets the staff pamper ...  Read more

Location: Basseterre, St Kitts
Duration: Flexible

From USD $650.00

Afternoon Pirate Sail and Snorkel Cruise in Aruba

5 star rating: Highly Recommended 1 Review

Enjoy an afternoon snorkeling cruise in Aruba aboard this 85-foot teak Schooner. Visit three great sites: Malmok Reefs, Boca Catalina and the WWII shipwreck, ...  Read more

Location: Oranjestad, Aruba
Duration: 3 hours

From USD $45.00

Catalina Bay and Antilla Shipwreck Snorkel Cruise

4.5 star rating: Recommended 30 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 ...  Read more

Location: Aruba
Duration: 3 hours

From USD $60.99

St. Maarten 12 Metre Challenge

5 star rating: Highly Recommended 20 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 $95.00

Catamaran Day Trip to Saona

Leaving from Bayahibe or Punta Cana hotels, you'll travel by catamaran to the most beautiful island of the Dominican Republic: Saona. This full day tour will ...  Read more

Location: La Romana, Dominican Republic
Duration: 9 hours

From USD $66.00

Catamaran Sail and Snorkel in Fajardo

4 star rating: Recommended 1 Review

Enjoy a day out on the water in Fajardo! Sway to the sound of island music as you sail along the white sand, clear water cays of La Cordillera Nature Reserve. ...  Read more

Location: Fajardo, Puerto Rico
Duration: 6 hours

From USD $81.39

San Juan Bay Day Sail

5 star rating: Highly Recommended 3 Reviews

Discover San Juan, Puerto Rico aboard a sailboat. Take in the panoramic views on this pleasure sightseeing tour of San Juan Bay and ...  Read more

Location: San Juan, Puerto Rico
Duration: 90 minutes

From USD $70.00

Palm Pleasure Sunset Sail

4.5 star rating: Recommended 21 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

From USD $63.99

Let's Go Sailing to St Barts

5 star rating: Highly Recommended 2 Reviews

Tiime to sail to St Barts! Join us for an exclusive sail, snorkel and sightseeing tour leaving from Dock Maarten. Stops will include Ilet Fourchue, ...  Read more

Location: Sint Maarten, Netherlands
Duration: 9 hours

From USD $139.00
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Only Show: Airboat Tours | Brunch Cruises | Day Cruises | Dinner Cruises | Dolphin & Whale Watching | Glass Bottom Boat Tours | Gondola Cruises | Lunch Cruises | Multi-day Cruises | Night Cruises | Sailing Trips | Submarine Tours | Sunset Cruises

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