Caribbean Sailing Trips

Caribbean Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: Airboat Tours | Brunch Cruises | Catamaran 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

Sort by:
Viewing 1 of 3

Page: 1 | 2 | 3 | Next

St Thomas Snorkel and Sail Adventure to St John

5 star rating: Highly Recommended 31 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

Anguilla Day Trip from St Maarten Including Lunch

5 star rating: Highly Recommended 60 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

Private Sailing Charter in St Kitts

5 star rating: Highly Recommended 4 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

7 Day Sailing in the British Virgin Islands: Explore the Caribbean Paradise

Ever dreamed of sailing the Caribbean waters? Whether you are taking a flotilla holiday for the first time or you are an experienced “sailor”, island hopping ...  Read more

Location: Tortola, British Virgin Islands
Duration: 8 days

From USD $1,816.52

Barbados Catamaran Snorkeling Cruise

5 star rating: Highly Recommended 32 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 Kitts Deluxe Catamaran Snorkeling Tour With Lunch

5 star rating: Highly Recommended 23 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

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

Happy Hour Sail and Snorkel in Aruba with Optional Snuba

4.5 star rating: Recommended 28 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

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, Gustavia ...  Read more

Location: Sint Maarten, Netherlands
Duration: 9 hours

From USD $139.00

Nassau Sail and Snorkel Tour

4.5 star rating: Recommended 12 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

Afternoon Pirate Sail and Snorkel Cruise in Aruba

4.5 star rating: Recommended 2 Reviews

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

St. Maarten 12 Metre Challenge

5 star rating: Highly Recommended 21 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

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

Day Trip to the Island of Prickly Pear from St Maarten

5 star rating: Highly Recommended 66 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

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

Bermuda Catamaran Sail and Snorkel Tour

5 star rating: Highly Recommended 37 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 $69.99

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

St Kitts Snorkel Cruise with Lunch

3.5 star rating: Worth doing 2 Reviews

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

From USD $97.00

Antigua Shore Excursion: Yacht Racing

5 star rating: Highly Recommended 5 Reviews

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

From USD $120.00

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

Cayman Islands Stingray City Luxury Sailing and Swimming Tour

5 star rating: Highly Recommended 1 Review

Sail in the spacious and comfortable Allura catamaran and snorkel in the world famous waters of Grand Cayman’s stingray sandbar.

Location: George Town, Cayman Islands
Duration: 3 hours

From USD $69.99

St Maarten Sunset Schooner Cruise

4.5 star rating: Recommended 3 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

Grand Cayman Kittiwake and Reef Sail

Take a relaxing cruise along the picturesque shores of Seven Mile Beach and enjoy some of the best snorkeling on Grand Cayman! Visit both a wreck and a reef on ...  Read more

Location: George Town, Cayman Islands
Duration: 2 hours 30 minutes

From USD $70.00

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

St Lucia Sailing Tour on Rodney Bay

Put your Caribbean vacation to good use by learning the basics of sailing on this half-day tour. Out on the waters of Rodney Bay with a highly trained crew, ...  Read more

Location: St Lucia
Duration: 3 hours

From USD $98.99
Viewing 1 of 3

Page: 1 | 2 | 3 | Next

Only Show: Airboat Tours | Brunch Cruises | Catamaran 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

Get the
Inside Scoop

Privacy Policy

Call (888) 651-9785

Viator uses cookies to improve your experience on our website. Learn more about how we use cookies and how to change your cookie settings | Close message