Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 693 Sailing Trips activities in North America. Sort by Popularity. - Page 2St. Augustine Live Music Sunset Sail with Drinks Included
Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sail! Indulge in complimentary beer, wine, soda, water, margaritas, champagne, and a snack, while enjoying live performances by some ... More

St. Augustine Live Music Sunset Sail with Drinks Included
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North America
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Superb170 reviews4.8
Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sai....
Seattle Sunset Sail BYOB
Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunset Sail is powered by the wind, so it is extremally Eco-Friendly. We are one of the only cruises in the area that allow you to brin... More
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Seattle Sunset Sail BYOB
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North America
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Superb105 reviews4.9
Our Sunset Sail is one of the most relaxing and affordable activities in Downtown Seattle. The Sunse....
Free Cancellation
(Saving 12% )
Key West Snorkeling with Breakfast and Unlimited Mimosas
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More

Key West Snorkeling with Breakfast and Unlimited Mimosas
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North America
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Exellent524 reviews4.5
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain
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North America
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Very Good402 reviews4
Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....
Sunset Sail in Key West with Beverages Included
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More

Sunset Sail in Key West with Beverages Included
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North America
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Superb825 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
Award Winning Cozumel Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip. Enjoy Cozumel's top attractions and most visited reefs in the C... More

Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
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North America
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Exellent1,339 reviews4.3
Award Winning Cozumel Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire th....
Day's End Cocktail Sunset Sail
Bring the whole family along for this upscale evening of outstanding food and beverages. We set the sails and chase the sun as it sets into the distant horizon of the azure water of the South Pacific. This casual dining experience... More

Day's End Cocktail Sunset Sail
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North America
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Superb26 reviews4.8
Bring the whole family along for this upscale evening of outstanding food and beverages. We set the ....
Deluxe Sunset & Day Sail Small Group
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect for up to six passengers. Glide through calm waters as the sky transforms into a masterpiece of color. Keep an eye out for playfu... More

Deluxe Sunset & Day Sail Small Group
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North America
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Superb145 reviews5
Experience the breathtaking beauty of San Diego Bay at sunset aboard our mono-hull sailboat, perfect....
Private Catamaran Escape for 2–6 Guests – Celebrate Your Way”
Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re celebrating a bachelorette, a birthday, or simply enjoying time with your favorite people, this catamaran getaway for up to six gues... More
Private Tour

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way....
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North America
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Superb302 reviews4.9
Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re ce....
Private Tour
2-Hour Seattle Sailing Harbor Tour
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way to see the Seattle skyline, the beauty of the Puget Sound, even mountain views! We ... More
Private Tour

2-Hour Seattle Sailing Harbor Tour
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North America
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Superb391 reviews4.7
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....
Private Tour
Turtles & Tacos Luxury Catamaran Snorkel
As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are eager to guide you on an unforgettable journey. The vessel is equipped with all the amenities you need for a comfortable and enjoy... More
Private Tour

Turtles & Tacos Luxury Catamaran Snorkel
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North America
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Superb32 reviews4.8
As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are ....
Private Tour
Sunset Catamaran Cruise in Ft. Lauderdale
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More
Private Tour

Sunset Catamaran Cruise in Ft. Lauderdale
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North America
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Superb655 reviews4.8
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....
Private Tour
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 a... More
Private Tour

Afternoon Sail & Snorkel to the Captain Cook Monument
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North America
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Superb680 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....
Private Tour
Deluxe Sail & Snorkel to the Captain Cook Monument
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 adventure will begin in the turquoise waters a... More
Private Tour

Deluxe Sail & Snorkel to the Captain Cook Monument
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North America
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Superb476 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....
Private Tour
Classic Tall Ship Sightseeing Cruise of Boston Harbor
Come out for a day sail adventure in Boston Harbor aboard our classic schooner, the Liberty Star. Get away from the hustle and bustle of the city streets and enjoy some quality time out on the water with unbeatable views of the ci... More
Private Tour

Classic Tall Ship Sightseeing Cruise of Boston Harbor
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North America
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Superb473 reviews4.7
Come out for a day sail adventure in Boston Harbor aboard our classic schooner, the Liberty Star. Ge....
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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Superb392 reviews4.7
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....
Private Tour
Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club
Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among vibrant tropical fish, then relax on Playa Norte, one of Mexico's finest beaches. Departing from the pier, begin with a 30-minut... More
Private Tour

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club
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North America
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Superb110 reviews4.7
Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among ....
Private Tour
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More
Private Tour

Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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North America
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Superb793 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Private Tour
Kona-Kohala Coast Sunset Sail by Catamaran
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon. You may even see the green flash. Board from Anaehoomalu Bay (A-Bay) to sail... More
Private Tour

Kona-Kohala Coast Sunset Sail by Catamaran
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North America
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Superb349 reviews4.7
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....
Private Tour
Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your loved ones to experience a beautiful Snorkeling, Sailing Cruise, and Whale Watching (Dec-Apr) on our Small Charming Hawaiian Catamara... More
Private Tour

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....
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North America
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Superb143 reviews4.7
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....
Private Tour