Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 719 Sailing Trips activities in North America. Sort by Popularity. - Page 5Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas
✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unforgettable snorkeling, sightseeing and sailing adventure. Begin at Pelican’s Rock, dive into crystal-clear waters filled with hun... More

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas
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North America
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Superb785 reviews4.9
✨ Discover Los Cabos Like Never Before! Sail the turquoise waters of the Sea of Cortez on an unfor....
Sunset Lighthouse Cruise Along Casco Bay
Embark on an unforgettable 1.5-hour cruise along Maine's breathtaking coastline at sunset. See four of Maine's most iconic lighthouses, spot seals and seabirds, and take in the historic forts that dot the landscape. Bring your fav... More

Sunset Lighthouse Cruise Along Casco Bay
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North America
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Superb35 reviews4.8
Embark on an unforgettable 1.5-hour cruise along Maine's breathtaking coastline at sunset. See four ....
Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More

Afternoon Sail & Snorkel to the Captain Cook Monument
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North America
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Superb243 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....
Newport Sightseeing Day Sailing Experience on Schooner Adirondack
See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges, lighthouses and more during this 1.5-hour experience!... More

Newport Sightseeing Day Sailing Experience on Schooner Adirondack
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North America
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Superb67 reviews4.9
See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schoone....
Newport Afternoon Sightseeing Sail on Classic Sailboat
Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail, including Newport's historic lighthouses and landmarks, bridges, mansions a... More

Newport Afternoon Sightseeing Sail on Classic Sailboat
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North America
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Superb142 reviews4.8
Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narraga....
Schooner Fame Sailing Tour
FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per TripAdvisor. Don't miss the very best of what Salem has to offer! There's more to our town than witches! FAME is a full-scale replica... More

Schooner Fame Sailing Tour
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North America
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Superb562 reviews4.9
FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per Trip....
Catamaran Sunset Sail Premium 2.5hr Small group w/ drinks
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

Catamaran Sunset Sail Premium 2.5hr Small group w/ drinks
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North America
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Superb198 reviews4.9
Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and loungi....
2-Hour Oahu Sunset Catamaran Sail
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for... More

2-Hour Oahu Sunset Catamaran Sail
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North America
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Superb110 reviews4.9
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....
San 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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Superb626 reviews4.9
Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sa....
Newport Sunset Sail on Schooner Adirondack
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! 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 sailbo... More

Newport Sunset Sail on Schooner Adirondack
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North America
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Superb79 reviews4.9
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of th....
Mexico City: Xochimilco at sunrise + Breakfast and transportation
Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural beauty, the tranquility of the sunrise and respect for the environment. This is not the traditional Xochimilco of the trajineras;... More

Mexico City: Xochimilco at sunrise + Breakfast and transportation
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North America
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Superb90 reviews5
Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural....
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

Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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North America
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Superb145 reviews4.9
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
Sunset Cocktail Cruise from Anaeho'omalu Bay
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More

Sunset Cocktail Cruise from Anaeho'omalu Bay
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North America
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Superb60 reviews4.8
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....
Private Classic Sailboat Tour in New York City
This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a unique and immersive experience on the Hudson River. You'll enjoy stunning views of iconic landmarks like the Statue of Liberty, E... More
Private Tour

Private Classic Sailboat Tour in New York City
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North America
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Superb1 review5
This private sailing tour with Empire Yacht Charters, led by the charismatic Captain Andy, offers a ....
Private Tour
Key West Reef Snorkel & Sail Adventure
Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More
Private Tour

Key West Reef Snorkel & Sail Adventure
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North America
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Superb533 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Private Tour
Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music
Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. In Cancun, you have an incredible opportunity to fall in love again at the rhythm of the live sax with a sunset as enchanting as t... More
Private Tour

Amazing Romantic Dinner on a Spanish Galeon with Saxophone Music
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North America
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Superb96 reviews4.6
Have you run out of ideas to celebrate love with your partner? Imagine reconquering your true love. ....
Private Tour
Southwest Florida Sunset Sail
SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The sunset hours are a magical time to be out on the water. With the winds calm, the sun turns g... More
Private Tour

Southwest Florida Sunset Sail
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North America
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Superb452 reviews4.9
SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....
Private Tour
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty of interesting whale information Convenient location walking... More
Private Tour

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
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North America
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Superb147 reviews4.7
Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....
Private Tour
Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar
*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service throughout the excursion. *Take a moment for a photo opportunity with y... More
Private Tour

Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open....
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North America
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Superb74 reviews4.6
*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting ....
Private Tour
Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience
Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own private catamaran. Complete with a professional captain & crew , your group will enjoy spacious accommodations and a premium, pers... More
Private Tour

Lagoon 39ft Private Catamaran 5hr - El Cielo Full Experience
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North America
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Superb565 reviews5
Our 5 Hrs private charter delivers the ultimate all-inclusive vacation on the water aboard your own ....
Private Tour