Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 719 Sailing Trips activities in North America. Sort by Popularity. - Page 7Suncoast Sailing's Sunset Sailing Experience!
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Treasure Island, Florida! You’ll set sail about an hour before sunset to give you plenty of time to catch the full range of hues p... More

Suncoast Sailing's Sunset Sailing Experience!
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North America
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Superb239 reviews4.9
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....
Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar
Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the best reefs and see beautiful tropical fish. Enjoy a delicious buffet lunch on our private beach club, and then tour Isla Mujeres to s... More

Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar
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North America
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Very Good204 reviews3.7
Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the bes....
San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included
Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica of a 1904 gaff rigged friendship sloop. She is an elegant sight under sail, featuring; highly finished woodwork, bronze fixtures, a... More

San Diego Bay Sail Aboard a Vintage Yacht Beer and Wine Included
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North America
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Superb324 reviews4.9
Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica o....
Puerto Vallarta Luxury Sailing with Premium Open bar & lunch
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra Madre mountains. This small-group experience offers a perfe... More

Puerto Vallarta Luxury Sailing with Premium Open bar & lunch
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North America
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Superb293 reviews4.8
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breat....
New York City Sailboat Day Cruise to the Statue of Liberty
Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides along the Hudson Rive... More

New York City Sailboat Day Cruise to the Statue of Liberty
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North America
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Superb150 reviews4.8
Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by t....
Bimini or Grand Bahama Island by Ferry
Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Florida! Picture this: pristine white beaches, crystal-clear turquoise waters, and tons of fun activities waiting for you. We'll pick... More

Bimini or Grand Bahama Island by Ferry
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North America
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Very Good15 reviews3.7
Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Flor....
St Augustine Nights of Lights w Drinks and Live Music Sunset Sail
Come celebrate the magic of the Nights of Lights celebration with us from the water! Experience Historic St. Augustine from a whole new vantage point—aboard a boat cruise that offers unforgettable views and festive fun. After t... More

St Augustine Nights of Lights w Drinks and Live Music Sunset Sail
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North America
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Exellent45 reviews4.5
Come celebrate the magic of the Nights of Lights celebration with us from the water! Experience His....
Halifax Sunset Cruise Ft. a Live Musician
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on the Halifax Sunset Cruise aboard our signature ship, the Tall Ship Silva. Purchase wine, beer, cocktails, and other beverages from... More

Halifax Sunset Cruise Ft. a Live Musician
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North America
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Superb46 reviews4.7
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on ....
Key West: Sunset Sail + Reef Snorkel & Sandbar
Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • Guided Snorkeling Your mate hops in the water with you and points out animals and shows yo... More

Key West: Sunset Sail + Reef Snorkel & Sandbar
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North America
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Superb29 reviews5
Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. Wh....
Private Luxury Daytime Boat Tour in New York City - 1 Hour
Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time, then climb aboard a luxurious, 28-foot powerboat cruiser and enjoy a relaxing and comfortable journey around lower Manhattan. En... More
Private Tour

Private Luxury Daytime Boat Tour in New York City - 1 Hour
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North America
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Superb39 reviews4.9
Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time....
Private Tour
One Hour Cruise Around Marina del Rey
Explore Los Angeles' best-kept secret on a classic boat tour of Marina del Rey. See the city, admire the yachts of the rich and famous, enjoy the fresh air, and look for wildlife like sea lions.... More
Private Tour

One Hour Cruise Around Marina del Rey
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North America
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Exellent29 reviews4.2
Explore Los Angeles' best-kept secret on a classic boat tour of Marina del Rey. See the city, admire....
Private Tour
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More
Private Tour

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
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North America
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Superb233 reviews4.9
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....
Private Tour
Sailing on Historic Schooner Yacht in Salem, MA
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. Winner of the 1930 and 1932 Newport to Bermuda race and open... More
Private Tour

Sailing on Historic Schooner Yacht in Salem, MA
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North America
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Superb169 reviews4.9
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....
Private Tour
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More
Private Tour

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
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North America
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Exellent69 reviews4.5
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
Private Tour
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More
Private Tour

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise
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North America
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Superb69 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Private Tour
Sunset Sail Aboard the 47 ft Daydreams Sailboat
Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way. Wit... More
Private Tour

Sunset Sail Aboard the 47 ft Daydreams Sailboat
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North America
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Superb29 reviews4.9
Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Gran....
Private Tour
Key West Champagne Sunset Catamaran Cruise
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy included wine, sparkling wine, beer, sangria or margaritas on board the boat. . As you sail thr... More
Private Tour

Key West Champagne Sunset Catamaran Cruise
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North America
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Superb579 reviews4.7
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of t....
Private Tour
Deluxe Day Sail in San Diego
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego Bay offer a perfect blend of adventure and relaxation. With our passionate and kno... More
Private Tour

Deluxe Day Sail in San Diego
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North America
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Superb55 reviews5
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....
Private Tour
Newport Sunset Sail on Classic Sailboat
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailboat and see all of Newport's iconic sights from the water including histor... More
Private Tour

Newport Sunset Sail on Classic Sailboat
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North America
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Superb41 reviews4.8
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....
Private Tour
Los Cabos Catamaran Cruise with Open Bar & Light Snack
Experience Los Cabos from the best seat in the house — aboard a spacious catamaran cruising past its most iconic landmarks. Sail along the dazzling Cabo coastline to The Arch (El Arco), Lover’s Beach, and Divorce Beach, where ... More
Private Tour

Los Cabos Catamaran Cruise with Open Bar & Light Snack
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North America
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Superb6 reviews4.8
Experience Los Cabos from the best seat in the house — aboard a spacious catamaran cruising past i....
Private Tour