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Sailing Trips

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2-Hour Monterey Bay Family Sailing Cruise

2-Hour Monterey Bay Family Sailing Cruise

Choose from two departure times when you book. 10:45 AM, or 1:00 PM.  Please add a note with your booking…



2.5 Hour San Diego Sunset Sail

2.5 Hour San Diego Sunset Sail

Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that…



3 Hour Private Sail For Up To 6 People

3 Hour Private Sail For Up To 6 People

Feel the wind in your hair as you sail through the bay as you sip on wine or champagne! With…



90 Min Key West Harbor Sail

90 Min Key West Harbor Sail

This 90 minute sailing trip in Key West is the best way to experience the water with friends and/or family…



All Inclusive Water Adventure Excursion in Key West

All Inclusive Water Adventure Excursion in Key West

This full day excursion from Key West includes all the fun things to do in the ocean - kayaking, snorkeling…



America's Cup Afternoon Sail

America's Cup Afternoon Sail

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars…



America's Cup Sailing Adventure on San Francisco Bay: Day Sail

America's Cup Sailing Adventure on San Francisco Bay: Day Sail

Welcome aboard for a thrilling 2.5 hour sailing adventure aboard USA 76, an International America’s Cup Class racing yacht that…



America's Cup Sailing Adventure on San Francisco Bay: Express Sail

America's Cup Sailing Adventure on San Francisco Bay: Express Sail

Welcome aboard for a family friendly 2 hour San Francisco Bay sailing tour aboard USA 76, an International America’s Cup…



America's Cup Sailing Adventure on San Francisco Bay: Sunset Sail

America's Cup Sailing Adventure on San Francisco Bay: Sunset Sail

Welcome aboard for a thrilling 2.5 hour sailing adventure culminating with sunset over San Francisco Bay. We will sail aboard…



Bugeye Backcountry Schooner Eco Tour

Bugeye Backcountry Schooner Eco Tour

Set sail aboard our classically-styled schooner as she departs the Historic Key West Seaport for a full day of sailing…



Catamaran Sailing and Snorkel Adventure on Kaneohe Bay

Catamaran Sailing and Snorkel Adventure on Kaneohe Bay

Sail and snorkel in Oahu's Kaneohe Bay during a 3-hour cruise aboard a small catamaran. Set sail from He’eia State…



City Lights Sail on Adirondack

City Lights Sail on Adirondack

Experience New York City lights like you never have on this sail along the bright and beautiful borough of Manhattan.Key…



City Lights Sail on America 2

City Lights Sail on America 2

Board the 105-foot, 1851 revival,  Schooner America 2.0 after dusk to view the famous Manhattan skyline. Bring your favorite companion or…



Classic Sailboat Afternoon Harbor Tour

Classic Sailboat Afternoon Harbor Tour

Family-owned business offering small group sailing tours on San Diego Bay on a unique 1914 replica Friendship Sloop. All boat tours circle…



Classic Sailboat Sunset Sail

Classic Sailboat Sunset Sail

This unforgettable 2.5 hour tour will circle you around the San Diego harbor during the most dramatic part of a…



Craft Beer Sailing Cruise in New York City

Craft Beer Sailing Cruise in New York City

Step aboard one of the largest sailing ships in the US and cruise along New York Harbor while tasting some…



Day Sail to Statue of Liberty on Adirondack

Day Sail to Statue of Liberty on Adirondack

Offered April through early November: Experience New York like you never have before on this two-hour sail aboard the Adirondack, an…



Day Sail to Statue of Liberty on America 2

Day Sail to Statue of Liberty on America 2

Offering a premium sailing experience, the Schooner America 2.0 is the newest, largest, most elegant ship designed for our fleet. Added to…



Friday Night Bay Lights Sail

Friday Night Bay Lights Sail

Get a head start on your weekend with a Friday night sail aboard the classic schooner Freda B! We’ll sail…



Half-Day Cruise with Kayaking and Snorkeling

Half-Day Cruise with Kayaking and Snorkeling

Don't miss one of the top things to do in Key West—a half-day sailing tour where you can explore the…



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