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North America Sailing Trips

North America Sailing Trips

Cruises, Sailing & Water Tours See all

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

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Molokini Sail and Snorkel Adventure

5 star rating: Highly Recommended 37 Reviews

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or ...  Read more

Location: Maui, Hawaii
Duration: 5 hours (approx.)

From USD $110.02

Statue of Liberty Tall Ship Sailing Cruise

4.5 star rating: Recommended 48 Reviews

Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views of this grand city by day, at twilight or by night. You will ...  Read more

Location: New York City, New York
Duration: Varies

From USD $38.99

San Francisco Bay Sunset Catamaran Cruise

5 star rating: Highly Recommended 140 Reviews

Enjoy the serene San Francisco Bay at sunset on this evening with the Sunset Cruise aboard a luxurious catamaran. Sail by Alcatraz Island, under the Golden ...  Read more

Location: San Francisco, California
Duration: 1 hour 30 minutes (approx.)

From USD $49.99

Los Cabos Luxury Snorkel and Lunch Cruise

5 star rating: Highly Recommended 11 Reviews

Enjoy a relaxing half-day cruise aboard a luxury yacht off the Cabo coast. Indulge in several hours of free time to hang out in the pristine water and take it ...  Read more

Location: Los Cabos, Mexico
Duration: 4 hours (approx.)

From USD $108.99

San Francisco Bay Sailing Cruise

5 star rating: Highly Recommended 84 Reviews

Experience San Francisco's urban beauty on a catamaran cruise on San Francisco Bay. Sail away from the urban feel of the city and experience all of San ...  Read more

Location: San Francisco, California
Duration: 1 hour 30 minutes (approx.)

From USD $39.99

Na Pali Coast Kauai Snorkel and Sail

5 star rating: Highly Recommended 13 Reviews

Come aboard this Na Pali kayaking trip where lush valleys and cliffs await. As you head to your destination, your crew will entertain you with stories of the ...  Read more

Location: Kauai, Hawaii
Duration: 5 hours 30 minutes (approx.)

From USD $142.26

Small-Group San Diego Sailing Excursion

5 star rating: Highly Recommended 8 Reviews

Set sail from San Diego on this small-group sailing tour! Choose from a daytime sail in San Diego Harbor or a sunset sail on the open ocean. This three-hour ...  Read more

Location: San Diego, California
Duration: 3 hours (approx.)

From USD $84.99

Champagne Celebration Sunset Cruise

5 star rating: Highly Recommended 40 Reviews

Get out on Key West’s beautiful Atlantic waters to sip Moët & Chandon champagne while enjoying the sunset. Included in the tour price are Chandon Brut ...  Read more

Location: Key West, Florida
Duration: 2 hours (approx.)

From USD $73.99

Craft Beer Sailing Cruise in New York City

5 star rating: Highly Recommended 3 Reviews

Step aboard one of the largest sailing ships in the US and cruise along New York Harbor while tasting some of New York’s best craft beers. Sip crisp ales and ...  Read more

Location: New York City, New York
Duration: 1-hour and 45-minutes

From USD $64.99

New York Harbor Evening Sail with Live Jazz

5 star rating: Highly Recommended 7 Reviews

Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views of New York City on this entertaining evening jazz sail. ...  Read more

Location: New York City, New York
Duration: 2 hours (approx.)

From USD $58.99

New York Sailboat Cruise with Wine, Cheese and Charcuterie

4 star rating: Recommended 3 Reviews

Step aboard New York City’s only floating designated landmark and cruise along New York Harbor while tasting some of America’s best-known wines. During your ...  Read more

Location: New York City, New York
Duration: 2 hours (approx.)

From USD $94.99

Oahu Combo Adventure: Bike, Sail and Snorkel

4.5 star rating: Recommended 10 Reviews

Bike, sail & snorkel on Oahu on this exhilarating combo tour! Explore lush rainforest and sparkling ocean all in one day! Roundtrip Waikiki hotel ...  Read more

Location: Oahu, Hawaii
Duration: 5 hours 30 minutes (approx.)

From USD $109.99

Luxury Catamaran Cruise from Oahu

4.5 star rating: Recommended 14 Reviews

Take a 2-hour sail through the waters of Hawaii on one of the fastest & most luxurious catamarans in Honolulu. Cruise the coast and open water alongside ...  Read more

Location: Oahu, Hawaii
Duration: 2 hours (approx.)

From USD $69.00

Boston Tall Ship Day Cruise

Admire the sights of Boston from an amazing vantage point – from the water! On a morning or afternoon cruise, travel back in time as you sail smoothly along ...  Read more

Location: Boston, Massachusetts
Duration: 1.5 to 3 hours

From USD $39.90

Shipwreck Snorkel and Wild Dolphin Encounter

4.5 star rating: Recommended 20 Reviews

Spend a beautiful Florida day out in the clear, blue waters off Key West. On the Key West Shipwreck Snorkel and Wild Dolphin Encounter cruise, you’ll spot ...  Read more

Location: Key West, Florida
Duration: 4 hours (approx.)

From USD $95.59

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

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