Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 668 Sailing Trips activities in North America. Sort by Popularity. - Page 5San Francisco Bay Sailing Cruise
Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from the vantage point of the water. You’ll coast past the city skyline, the Gold... More

San Francisco Bay Sailing Cruise
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North America
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Superb591 reviews4.9
Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sa....
FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry
Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the world's best beaches. The ocean crossing is provided with our comfortable Express-Ferry featuring restrooms, comfortable seats, air ... More
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FROM FLORIDA: Bimini Bahamas Day Trip By Fast Ferry
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North America
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Very Good10 reviews3.6
Take advantage of the vicinity of the Bahamas Islands during your Florida visit to experience the wo....
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Key West Sunset Sail Aboard Legendary Schooner Appledore
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More

Key West Sunset Sail Aboard Legendary Schooner Appledore
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North America
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Superb181 reviews5
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....
Private Sailing Charter with Captain, BYOB
Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More
Private Tour

Private Sailing Charter with Captain, BYOB
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North America
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Superb49 reviews5
Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6....
Private Tour
Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling
Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing cruise. Explore pristine beaches and beautiful sights while savoring fresh guacamole and a selection of delicious snacks. This pe... More
Private Tour

Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling
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North America
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Superb56 reviews5
Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing ....
Private Tour
2.5 Hours of Fun: Catamaran Sunset Sail
Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and lounging around watching sea life, and water rush by. The swift and stable ocean design ensures a comfortable, and exhilarating ride wit... More
Private Tour

2.5 Hours of Fun: Catamaran Sunset Sail
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North America
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Superb149 reviews4.9
Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and loungi....
Private Tour
Snorkel with Manta Rays Guaranteed
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More
Private Tour

Snorkel with Manta Rays Guaranteed
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North America
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Superb680 reviews4.8
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....
Private Tour
Kealakekua Snorkel and Sail Adventure
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral garde... More
Private Tour

Kealakekua Snorkel and Sail Adventure
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North America
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Superb631 reviews5
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the....
Private Tour

9am Turtle Canyon Snorkel Adventure
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More
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Private Tour
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9am Turtle Canyon Snorkel Adventure
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North America
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Superb248 reviews4.9
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
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Private Tour
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Key West Dolphin and Snorkel Experience
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North America
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Exellent274 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
Private Tour
Private Guided Sunset and Dolphin Cruise up to 6 Passengers
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a cooler with bottled water a... More
Private Tour

Private Guided Sunset and Dolphin Cruise up to 6 Passengers
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North America
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Superb58 reviews5
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....
Private Tour
Panama City Beach Sunset Sail on The Footloose Catamaran
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More
Private Tour

Panama City Beach Sunset Sail on The Footloose Catamaran
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North America
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Superb394 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
Private Tour
Dolphin Adventure Sail in Cocoa Beach
Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter pla... More
Private Tour

Dolphin Adventure Sail in Cocoa Beach
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North America
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Superb134 reviews5
Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....
Private Tour
Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More
Private Tour

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail
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North America
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Exellent348 reviews4.4
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....
Private Tour
Sightseeing Day Sail around Boston Harbor
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle... More
Private Tour

Sightseeing Day Sail around Boston Harbor
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North America
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Superb382 reviews4.7
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....
Private Tour
NYC Statue of Liberty Tall Ship Sail aboard Clipper City
Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views of this grand city by day. You will enjoy breathtaking views of New York City and see the Statue of Liberty, Ellis Island, the Manh... More
Private Tour

NYC Statue of Liberty Tall Ship Sail aboard Clipper City
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North America
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Exellent253 reviews4.3
Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views o....
Private Tour
Sail and Turtle Snorkeling Tour in Waikiki
Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an epic 2-hour boat adventure that combines the thrill of sailing past Diamond Head with the magic of snorkeling with turtles in their ... More
Private Tour

Sail and Turtle Snorkeling Tour in Waikiki
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North America
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Superb236 reviews4.9
Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an ep....
Private Tour
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More
Private Tour

Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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North America
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Superb106 reviews4.8
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
Private Tour
2-Hour Windjammer Sailing Trip in Maine with Licensed Captain
Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises.... More
Private Tour

2-Hour Windjammer Sailing Trip in Maine with Licensed Captain
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North America
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Very Good391 reviews4
Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....
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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Superb57 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Private Tour