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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. Enjoy a 2-hour captained sailing excursion with your family and friends on…



3 Hour San Diego Sunset Sail

3 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-Hr Private Endless Summer Special

3-Hr Private Endless Summer Special

This is a 3-Hour Private Sailing Charter that can accommodate up to SIX passengers.  A Licensed Captain will navigate your…



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…



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…



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 Harbor Morning Cruise

Classic Sailboat Harbor Morning Cruise

Experience the bustling activity of the bay, wildlife, and a stunning view of the city skyline on a San Diego…



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…



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…



Hawaii Pirate Ship Adventures

Hawaii Pirate Ship Adventures

Enjoy fun for the whole family during our live pirate show aboard the Treasure Seeker!  Join our pirates in their…



Java Cat Sail, Kayak and Snorkel Charter

Java Cat Sail, Kayak and Snorkel Charter

Combine three Key West activities on this eco-adventure by chartered catamaran. Sail to the Key West National Wildlife Refuge for…



Lobster and Beer Sail in New York City

Lobster and Beer Sail in New York City

Get on board for the unbeatable powerhouse pairing of eating and drinking on the water. Chow down on Luke's Lobster…



Luxury Scenic Sailing Tour

Luxury Scenic Sailing Tour

Whether you are on vacation or a local, this is an experience for you. Relax, enjoy snacks and beverages, listen…



New York City Burlesque Sail

New York City Burlesque Sail

Your invited to set sail on an adventure of seductive espionage around the Hudson and New York Harbor aboard a…



New York City Happy Hour Sail

New York City Happy Hour Sail

Sail smoothly from the end of your week into the start of your weekend on board Manhattan's most elegant sailing…



New York City Lights Sail

New York City Lights Sail

This 90-minute evening sail offers the perfect opportunity to sit back and relax while you take in close-up views of…



New York City Sunset Sail aboard Shearwater

New York City Sunset Sail aboard Shearwater

This 2-hour sunset sail will be the highlight of your New York City stay. Take in close-up views of the…



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