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 6 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

Day Trip to the Island of Prickly Pear from St Maarten

5 star rating: Highly Recommended 57 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 $109.99

Bermuda Sunset Cocktail Cruise

4.5 star rating: Recommended 6 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

Anguilla Day Trip from St Maarten

5 star rating: Highly Recommended 53 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 $113.99

Nassau Sail and Snorkel Tour

5 star rating: Highly Recommended 4 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

Catamaran Cruise with Snorkeling, Paddleboarding and Kayaking

5 star rating: Highly Recommended 17 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

Small-Group Day Sail in St Maarten

5 star rating: Highly Recommended 10 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 Afternoon Snorkeling Tour

5 star rating: Highly Recommended 7 Reviews

Enjoy your Caribbean adventure to the fullest on this 3-hour snorkel cruise from Aruba's De Palm Pier. Snorkel in the clear, calm waters of Boca Catalina to ...  Read more

Location: Aruba
Duration: 3 hours

From USD $44.99

Grand Cayman Sunset Catamaran Sail

4.5 star rating: Recommended 11 Reviews

Enjoy breathtaking views and spectacular scenery as you are exposed to a beautiful Cayman sunset. Set sail on your Grand Cayman sunset cruise ...  Read more

Location: George Town, Grand Cayman
Duration: 2 hours

From USD $44.99

Catamaran Sailing and Snorkeling Tour With Lunch

5 star rating: Highly Recommended 15 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 ...  Read more

Location: Basseterre, St Kitts
Duration: 4 hours

From USD $69.00

Happy Hour Sail and Snorkel in Aruba with Optional Snuba

4.5 star rating: Recommended 18 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

St Thomas Snorkel and Sail Adventure to St John

5 star rating: Highly Recommended 14 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

St Maarten Catamaran Snorkel Sail

5 star rating: Highly Recommended 14 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: Philipsburg or Simpson Bay, St Maarten
Duration: 8 hours

From USD $118.99

Aruba Palm Pleasure Snorkel Adventure

4.5 star rating: Recommended 24 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. Maarten 12 Metre Challenge

5 star rating: Highly Recommended 15 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 ...  Read more

Location: Philipsburg, St Maarten
Duration: 2.5 - 3 hours

From USD $104.99

Punta Cana Small-Group Sailing and Snorkeling Catamaran Tour

5 star rating: Highly Recommended 2 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 ...  Read more

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

From USD $79.00

Palm Pleasure Sunset Sail

4.5 star rating: Recommended 18 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

Barbados Catamaran Snorkeling Cruise

5 star rating: Highly Recommended 26 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

St Thomas Day Sail and Snorkel Excursion

Set sail with us and enjoy the beauty of the US Virgin Islands. Snorkel with reef fish, eels, stingrays and turtles. Or just relax and enjoy a ...  Read more

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

From USD $175.00

Cades Reef Snorkel Cruise

4.5 star rating: Recommended 2 Reviews

Enjoy a day out on the crystal clear waters on Antigua on this Cades Reef Snorkel Cruise. You'll head out to the island's finest snorkeling site, Cades ...  Read more

Location: St Johns, Antigua
Duration: 6 hours

From USD $142.99

Champagne Sunset Cruise in St Maarten

3 star rating: Worth doing 1 Reviews

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: Philipsburg, St Maarten
Duration: 2 hours

From USD $44.99

St Maarten Sunset Schooner Cruise

4 star rating: Recommended 2 Reviews

Enjoy a Caribbean sunset from the water on this St Maarten cruise by historical schooner. On board a sailboat that’s more than 100 years old, ...  Read more

Location: Simpson Bay, St Maarten
Duration: 2 hours

From USD $38.99

Catalina Bay and Antilla Shipwreck Snorkel Cruise

4.5 star rating: Recommended 27 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

San Juan Bay Day Sail

5 star rating: Highly Recommended 1 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

Catamaran and Snorkel Tour of Punta Cana

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
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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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