Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 674 Sailing Trips activities in North America. Sort by Popularity. - Page 132-Hour Morning Sail in San Diego
Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma, San Diego Bay and the downtown waterfront. This two-hour adventure on a Catalina sailboat is limited to a maximum of six (6) gues... More

2-Hour Morning Sail in San Diego
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North America
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Superb18 reviews5
Set sail from America's Cup Harbor on your morning sailing tour, and enjoy the sights of Point Loma,....

Tulum: Snorkeling and Private Sailing Tour
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North America
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Superb149 reviews4.9
We will enjoy a wonderful catamaran tour, powered only by the wind, we will be able to enjoy a spect....
Private Tour
Tour to The Arch and Lover's Beach (optional) from Cabo
This is a tour in a boat that will take you to Divorce Beach, Lover's Beach, the Arch, Land's End, and through the Marina. See it all in one tour! During this awesome experience, you will be able to see a great variety of tropical... More
Private Tour

Tour to The Arch and Lover's Beach (optional) from Cabo
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North America
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Superb3 reviews5
This is a tour in a boat that will take you to Divorce Beach, Lover's Beach, the Arch, Land's End, a....
Private Tour
Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani
Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. This 1.5-hour journey from Honokohau Harbor offers a chance to bask in the sun and enjoy the ocean breeze while taking in the breath... More
Private Tour

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani
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North America
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Superb35 reviews4.8
Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. Th....
Private Tour
Luxury Catamaran Sailing Charters in Maine
Sail in luxury on a 44-ft catamaran yacht! We are one of the only sailing catamaran charters in Maine, and our luxurious yacht makes for a relaxing and fun experience. Our catamaran is stable and does not bounce in waves, providin... More
Private Tour

Luxury Catamaran Sailing Charters in Maine
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North America
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Superb85 reviews4.9
Sail in luxury on a 44-ft catamaran yacht! We are one of the only sailing catamaran charters in Main....
Private Tour
Catamaran Sailing Cruise in Monterey
Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind to make for a peaceful and exciting cruise on the bay. On the way out of t... More
Private Tour

Catamaran Sailing Cruise in Monterey
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North America
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Superb11 reviews4.9
Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage af....
Private Tour
Sailing Charters in Wilmington
After a successful first season I am happy to be here for back to back seasons. Sail in style on the historic Wilmington river walk. Enjoy a personalized Charter experience with up to six guests. Very few sailboats are up for publ... More
Private Tour

Sailing Charters in Wilmington
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North America
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Superb141 reviews5
After a successful first season I am happy to be here for back to back seasons. Sail in style on the....
Private Tour
Majahuitas Island Pirate Ship Adventure
A Vallarta Pirate Ship tour invites you to sail away to explore the Isla Majahuitas Nature Reserve. Along the way, enjoy stops for swimming, snorkeling, kayaking and treasure hunts and a live pirate show onboard. All-inclusive Val... More
Private Tour

Majahuitas Island Pirate Ship Adventure
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North America
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Superb1 review5
A Vallarta Pirate Ship tour invites you to sail away to explore the Isla Majahuitas Nature Reserve. ....
Private Tour
Friday Night Firework Cruise in Waikiki
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More
Private Tour

Friday Night Firework Cruise in Waikiki
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North America
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Superb21 reviews4.8
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....
Private Tour
Dolphin Adventure Sail in Cocoa Beach
Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter playful dolph... More
Private Tour

Dolphin Adventure Sail in Cocoa Beach
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North America
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Superb129 reviews5
Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforg....
Private Tour
Private Whale Watching Sailing Tour
Amaze yourself appreciating our most awaited visitors of the year, the Humpback Whales! Book this half-day tour on a beautiful and comfortable sailboat while you enjoy the breeze , the sun and the tide while you look for whales, d... More
Free Cancellation
Private Tour
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Private Whale Watching Sailing Tour
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North America
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Superb6 reviews5
Amaze yourself appreciating our most awaited visitors of the year, the Humpback Whales! Book this ha....
Free Cancellation
Private Tour
(Saving 4% )
Come Sailing at Navy Pier Marina - Sunset Sail on Lake Michigan
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline... More
Private Tour

Come Sailing at Navy Pier Marina - Sunset Sail on Lake Michigan
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North America
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Superb24 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Private Tour
2-Hour Private Luxury Boat Tour in New York City
Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view of the Manhattan skyline, Freedom Tower, Brooklyn Bridge, Empire ... More
Private Tour

2-Hour Private Luxury Boat Tour in New York City
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North America
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Superb68 reviews5
Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manh....
Private Tour
Private sailing excursions, nice spacious sailboats.
We are a new sailboat tour agency in bacalar ~ are sailboats stand out with ease access, very comfortable, 2 canopy’s to keep you protected from the elements and a 5 star crew. We provide an atmosphere for you to take over and T... More
Private Tour

Private sailing excursions, nice spacious sailboats.
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North America
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Superb20 reviews4.9
We are a new sailboat tour agency in bacalar ~ are sailboats stand out with ease access, very comfor....
Private Tour
Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks
Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel safe sailing with highly trained and bilingual staff in this beautiful freshwater paradise. Our years of experience back us up. Qua... More
Private Tour

Bacalar: 4hr Private Sailing Tour with Guacamole & Drinks
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North America
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Superb91 reviews4.9
Explore the Bacalar Lagoon aboard a classic sailboat and enjoy a trip in privacy and comfort. Feel s....
Private Tour
Private Sunset Sailing with Dolphin and History Tours on Mystique
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and op... More
Private Tour

Private Sunset Sailing with Dolphin and History Tours on Mystique
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North America
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Superb23 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Snorkel Sail Adventure off Ka'anapali Beach, Maui
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More
Private Tour

Snorkel Sail Adventure off Ka'anapali Beach, Maui
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North America
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Superb9 reviews4.9
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....
Private Tour
2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests
Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to helping families create unforgettable memories. Our vessel is thoughtfully designed to be warm and inviting, featuring handcrafted yel... More
Private Tour

2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests
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North America
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Superb60 reviews5
Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to help....
Private Tour
6 Hours Private Yacht in Puerto Vallarta with Snorkeling & Beach
Sail on a 6-hour private trip aboard our 55-foot private yacht, ideal for up to 12 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer to ... More
Private Tour

6 Hours Private Yacht in Puerto Vallarta with Snorkeling & Beach
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North America
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Superb60 reviews5
Sail on a 6-hour private trip aboard our 55-foot private yacht, ideal for up to 12 passengers. We a....
Private Tour
Romantic Lobster Dinner Cruise at Sunset
Cruise across the scenic Nichupte Lagoon on an elegant Spanish Galeon, treating your better half to an amazing romantic experience and an exquisite 3-course dinner. Following you check-in, get aboard the spectacular ship under t... More
Private Tour

Romantic Lobster Dinner Cruise at Sunset
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North America
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Exellent6 reviews4.3
Cruise across the scenic Nichupte Lagoon on an elegant Spanish Galeon, treating your better half to ....
Private Tour