Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 14New York Sunset Schooner Cruise on the Hudson River
Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known as Schooner Adirondack - inspired by the pilot schooners of... More
Likely to Sell Out New York Sunset Schooner Cruise on the Hudson River
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North America
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Superb221 reviews4.9
Experience a New York City sunset from the water on this evening sightseeing sail past many famous w....
Excursion to Reefs in a transparent boat from Cancun
It is the only tour that includes a visit to the lagoon, where we can appreciate 2 types of marine life, in addition, the colors of the blanquizal of Cancun are something spectacular and there is a great diversity of marine life... More
Likely to Sell Out Excursion to Reefs in a transparent boat from Cancun
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North America
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Very Good8 reviews4
It is the only tour that includes a visit to the lagoon, where we can appreciate 2 types of marine l....
Spectacular Afternoon Sail on San Diego Bay
A unique small group two-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy spectacular views as your fun-loving, informative Captain shares his knowledge of sailing and San Diego. Get hands-on or sit back and enjoy ... More
Likely to Sell Out Spectacular Afternoon Sail on San Diego Bay
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North America
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Superb15 reviews5
A unique small group two-hour sailing experience aboard our 35-foot sailboat, Luna. Enjoy spectacula....
Nights of Lights Sailboat Tour St Augustine Sailing
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting ... More
Private Tour
Likely to Sell Out Nights of Lights Sailboat Tour St Augustine Sailing
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North America
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Superb4 reviews5
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experien....
Private Tour
Day Sails and Sunset tours on Schooner Surprise in Camden Maine
Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at most and have cushioned seating on board for all. Experienced crew will point out wild life, tell you history of our area and show... More
Private Tour
Likely to Sell Out Day Sails and Sunset tours on Schooner Surprise in Camden Maine
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North America
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Superb82 reviews4.9
Sail on board the only historic day sailing schooner out of Camden Maine. We carry 18 passengers at ....
Private Tour
Romantic Dinner on a Spanish Galeon in Cancun
Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner with the most wonderful scenary. This is the perfect opportunity to enjoy a delicious dinner while you fall in love with the liv... More
Private Tour
Likely to Sell Out Romantic Dinner on a Spanish Galeon in Cancun
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North America
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Exellent23 reviews4.3
Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner ....
Private Tour
Sail 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
Private Tour
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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Superb42 reviews4.9
Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sa....
Private Tour
Catamaran in Cozumel with snorkeling at El Cielo and open Bar
Snorkel, Sip & Celebrate in Cozumel’s Caribbean Paradise Your captain and crew welcome you aboard with open arms—and an open bar. Margaritas, beer, soft drinks, and bottled water flow as music fills the air and the sea sets t... More
Private Tour
Likely to Sell Out Catamaran in Cozumel with snorkeling at El Cielo and open Bar
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North America
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Very Good19 reviews3.9
Snorkel, Sip & Celebrate in Cozumel’s Caribbean Paradise Your captain and crew welcome you aboard....
Private Tour
Daytime Sailing Along San Diego's Skyline
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More
Private Tour
Likely to Sell Out Daytime Sailing Along San Diego's Skyline
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North America
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Superb146 reviews4.9
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....
Private Tour
Key West Wreckers Race Aboard Schooner America 2.0
Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern ... More
Private Tour
Likely to Sell Out Key West Wreckers Race Aboard Schooner America 2.0
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North America
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Superb11 reviews4.9
Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse abo....
Private Tour
Key West Night Cruise aboard Schooner America 2.0
Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy unobstructed views of the sweeping night sky and a fun adventure in Key West at night. Please ... More
Private Tour
Likely to Sell Out Key West Night Cruise aboard Schooner America 2.0
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North America
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Superb3 reviews5
Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night c....
Private Tour
12pm 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
Private Tour
Likely to Sell Out 12pm Turtle Canyon Snorkel Adventure
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North America
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Superb306 reviews4.8
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Private Tour
Likely to Sell Out
Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling
Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Vallarta´s Bay. You will be able to Sail, Snorkel, Swim and even Paddelboard in Los Arcos National Park, capturing beautiful views ... More
Free Cancellation
Private Tour
(Saving 15% )
Likely to Sell Out Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling
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North America
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Superb112 reviews4.9
Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Va....
Free Cancellation
Private Tour
(Saving 15% )
Clear Boat to Cabo Lands End, The Arch and more
Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most uniquely, in a clear boat. You will take a tour just where the Pacific Ocean meets the Sea of Cortez, the famous Lands End. In our... More
Private Tour
Likely to Sell Out Clear Boat to Cabo Lands End, The Arch and more
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North America
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Exellent15 reviews4.5
Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most ....
Private Tour
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
Private Tour
Likely to Sell Out Newport Sunset Sail on Schooner Adirondack
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North America
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Superb80 reviews4.9
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of th....
Private Tour
Private Swim, Snorkel & Sail on the Daydreams Sailboat
This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for f... More
Private Tour
Likely to Sell Out Private Swim, Snorkel & Sail on the Daydreams Sailboat
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North America
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Superb31 reviews5
This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bo....
Private Tour
Private Kelowna Sailing Cruise on Okanagan Lake
Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are welcome to sit back and relax, enjoy the sights, or take a turn at the helm, with instruction from your skipper! I will never forg... More
Private Tour
Likely to Sell Out Private Kelowna Sailing Cruise on Okanagan Lake
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North America
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Superb42 reviews5
Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are w....
Private Tour
City Tour & Beach Club All Inclusive W Horse Ride & Water Sports
Experience the ultimate vacation with our all-inclusive tour! Sit back and relax as you are transported in a luxurious, air-conditioned vehicle, complete with complimentary beverages. Our tour includes visits to the stunning cathe... More
Private Tour
Likely to Sell Out City Tour & Beach Club All Inclusive W Horse Ride & Water Sports
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North America
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Good5 reviews3.4
Experience the ultimate vacation with our all-inclusive tour! Sit back and relax as you are transpor....
Private Tour
Newport Sunset Sail on Classic Sailboat
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 sailboat and see all of Newport's iconic sights from the water including histor... More
Private Tour
Likely to Sell Out Newport Sunset Sail on Classic Sailboat
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North America
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Superb42 reviews4.8
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....
Private Tour
Day Sailing Adventure in the Florida Marine Sanctuary
Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose our popular 3-hour Day Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailboat rides feature ... More
Private Tour
Likely to Sell Out Day Sailing Adventure in the Florida Marine Sanctuary
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North America
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Superb33 reviews5
Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay....
Private Tour