Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 9Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion
Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sail and create memories to cherish forever. Experience the beauty of Maine as you glide through the waters of the Saco River and Sa... More
Likely to Sell Out Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion
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North America
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Superb59 reviews4.9
Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sa....
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
Likely to Sell Out Key West Reef Snorkel & Sail Adventure
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North America
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Superb568 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Puerto Vallarta Adults-Only Luxury Sunset Sail
Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamarans. Relax and unwind as you enjoy delicious appetizers, a premium open bar, and top-tier service from our attentive crew. This i... More
Likely to Sell Out Puerto Vallarta Adults-Only Luxury Sunset Sail
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North America
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Superb447 reviews4.6
Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamar....
Best Private Luxury Sunset Boat Tour in New York City - 2 Hour
Experience the breathtaking beauty of New York City as the sun sets behind the Statue of Liberty and reflects off of the city skyline on this magical 2-hour sunset cruise around lower Manhattan! Get an unobstructed view of the Man... More
Private Tour
Likely to Sell Out Best Private Luxury Sunset Boat Tour in New York City - 2 Hour
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North America
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Superb29 reviews5
Experience the breathtaking beauty of New York City as the sun sets behind the Statue of Liberty and....
Private Tour
Sunset Dolphin Sail Aboard 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
Likely to Sell Out Sunset Dolphin Sail Aboard the Footloose Catamaran
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North America
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Superb482 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
2.5-hour Guided Sailboat Tour
2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, 159 Bridge Park Drive. Views of the Brooklyn Bridge, Statue of Liberty, World Trade Center, Ellis Island, Governor's Island and M... More
Private Tour
Likely to Sell Out 2.5-hour Guided Sailboat Tour
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North America
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Superb186 reviews5
2.5 hour sails for up to six passengers from Pier 5 in Brooklyn Bridge Park, One15 Brooklyn Marina, ....
Private Tour
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More
Private Tour
Likely to Sell Out Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling
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North America
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Superb467 reviews4.9
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....
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
Likely to Sell Out Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club
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North America
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Exellent172 reviews4.5
Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among ....
Private Tour
2hr Shared Sailing Experience in Toronto
On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out for the ferry, reported to be the shortest commercial one in the world. Below the water is a walking tunnel connecting the two for t... More
Private Tour
Likely to Sell Out 2hr Shared Sailing Experience in Toronto
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North America
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Superb26 reviews5
On a 2 hour sail, we tour the harbour and head to the lake through the western channel. Watch out fo....
Private Tour
Private Sunset Sail BYOB Dolphin/History Tours on 43ft 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
Likely to Sell Out Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique
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North America
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Superb59 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks
With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on the sea. 2.5 hour tour length is perfect for seeing all the beautiful sights. Catamarans reall... More
Private Tour
Likely to Sell Out 2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks
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North America
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Superb111 reviews5
With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepare....
Private Tour
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More
Private Tour
Likely to Sell Out 2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
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North America
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Superb2 reviews5
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....
Private Tour
Private Sailboat tour in Cabo San Lucas with Papillon Yachts
Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care of you to make this an unforgettable experience. Our all-inclusive and all-private tour will make sure you have everything you need... More
Private Tour
Likely to Sell Out Private Sailboat tour in Cabo San Lucas with Papillon Yachts
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North America
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Superb205 reviews5
Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care o....
Private Tour
Puerto Vallarta Private Yacht Adventure 5 hours + 1 hour Free
Sail on a private trip on board our private yacht 50 feet, ideal for up to 18 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 make t... More
Private Tour
Likely to Sell Out Puerto Vallarta Private Yacht Adventure 5 hours + 1 hour Free
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North America
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Superb15 reviews5
Sail on a private trip on board our private yacht 50 feet, ideal for up to 18 passengers. We are sur....
Private Tour
Waikiki Friday Night Fireworks Cruise
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More
Private Tour
Likely to Sell Out Waikiki Friday Night Fireworks Cruise
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North America
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Superb32 reviews4.6
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....
Private Tour
Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach
Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Partic... More
Private Tour
Likely to Sell Out Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach
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North America
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Superb278 reviews4.9
Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wil....
Private Tour
Likely to Sell Out
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 los arcos area while savoring fresh guacamole and a selection of delicious snacks. This personalized sailing expe... More
Free Cancellation
Private Tour
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Likely to Sell Out Half Day Private Sailing Cruise Puerto Vallarta with Snorkeling
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North America
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Superb65 reviews5
Experience the beauty of Puerto Vallarta’s stunning bay on an exclusive, half-day private sailing ....
Free Cancellation
Private Tour
(Saving 16% )
Likely to Sell Out
Windjammer Classic Day Sail from Camden, Maine
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More
Free Cancellation
Private Tour
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Likely to Sell Out Windjammer Classic Day Sail from Camden, Maine
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North America
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Superb452 reviews4.8
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....
Free Cancellation
Private Tour
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Likely to Sell Out
3hr Discover Sailing Adventure
Embark on a thrilling 3-hour introductory keelboat sailing experience designed for beginners eager to explore the basics of sailing. Guided by experienced instructors on our specially designed First 22 yacht, you’ll dive into es... More
Free Cancellation
Private Tour
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Likely to Sell Out 3hr Discover Sailing Adventure
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North America
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Superb13 reviews5
Embark on a thrilling 3-hour introductory keelboat sailing experience designed for beginners eager t....
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out
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
Free Cancellation
Private Tour
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Likely to Sell Out Key West: Sunset Sail + Reef Snorkel & Sandbar
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North America
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Superb55 reviews5
Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. Wh....
Free Cancellation
Private Tour
(Saving inf% )