Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 21Afternoon Half-Day Catmaran Sailing and Snorkel Adventure
Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This is the tour for you! Enjoy sailing in one of our Catamarans and we will ensure that you enjoy your afternoon to the maximum. The t... More
Afternoon Half-Day Catmaran Sailing and Snorkel Adventure
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North America
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Exellent72 reviews4.5
Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This ....
Schooner Applejack 2-Hour Day Sail from Boothbay Harbor
Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we set a c... More
Schooner Applejack 2-Hour Day Sail from Boothbay Harbor
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North America
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Exellent37 reviews4.4
Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....
NYC Statue of Liberty Tall Ship Sail aboard Clipper City
Step aboard the majestic Clipper City and feel the city fade into the background as the wind fills the sails. Glide through New York Harbor in style, with the Brooklyn Bridge, Statue of Liberty, Ellis Island, and the glittering Ma... More
Likely to Sell Out NYC Statue of Liberty Tall Ship Sail aboard Clipper City
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North America
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Exellent269 reviews4.3
Step aboard the majestic Clipper City and feel the city fade into the background as the wind fills t....
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
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....
Public Schooner Sail in Greenport
Set sail aboard the Bonnie Lynn for a delightful 2-hour public schooner experience in Greenport. Departing from Stirling Harbor, this sail offers the opportunity to enjoy the scenic beauty of the waters while indulging in a BYOB p... More
Likely to Sell Out Public Schooner Sail in Greenport
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North America
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Very Good19 reviews3.9
Set sail aboard the Bonnie Lynn for a delightful 2-hour public schooner experience in Greenport. Dep....
Private Afternoon Sailing/Dolphin & History Tour 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 since 2012, our sailing yachts are the highest quality and operated ... More
Private Tour
Likely to Sell Out Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique
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North America
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Superb34 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
New York City Skyline Night Sailboat Tour
Step aboard a beautiful sailboat, Schooner America 2.0, for a relaxing city lights tour around New York. See the New York City skyline, the Statue of Liberty and Ellis Island lit up at night. Sit back and relax while enjoying a pe... More
Private Tour
Likely to Sell Out New York City Skyline Night Sailboat Tour
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North America
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Superb13 reviews5
Step aboard a beautiful sailboat, Schooner America 2.0, for a relaxing city lights tour around New Y....
Private Tour
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
Private Tour
Likely to Sell Out 3hr Discover Sailing Adventure
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North America
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Superb10 reviews5
Embark on a thrilling 3-hour introductory keelboat sailing experience designed for beginners eager t....
Private Tour
Oyster Bay Two Hour Sailing Experience
Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and the impressive estates that line the bay. WINDSWEPT is metic... More
Private Tour
Likely to Sell Out Oyster Bay Two Hour Sailing Experience
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North America
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Superb2 reviews5
Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oys....
Private Tour
San Diego Sailing Private Activity
We are a hands on sailing adventure we encourage our guests to participate. Guests who chose to relax and enjoy the scenery and vibe are welcome to do so, you may bring beer or wine or other snacks no red wine please.... More
Private Tour
Likely to Sell Out San Diego Sailing Private Activity
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North America
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Superb1 review5
We are a hands on sailing adventure we encourage our guests to participate. Guests who chose to rela....
Private Tour
Amazing Romantic Dinner In Cancun On A Spanish Galeon The Best Sunset Activity
Have you run out of ideas to celebrate love with your partner? Imagine to reconquer 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 th... More
Private Tour
Likely to Sell Out Amazing Romantic Dinner In Cancun On A Spanish Galeon The Best Su....
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North America
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Superb1 review5
Have you run out of ideas to celebrate love with your partner? Imagine to reconquer your true love. ....
Private Tour
Key West Sunset Sail Aboard Legendary Schooner Appledore
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More
Private Tour
Likely to Sell Out Key West Sunset Sail Aboard Legendary Schooner Appledore
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North America
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Superb361 reviews5
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....
Private Tour
Skagway Trail and Sail
This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike Electric Bicycles where you will join us for a self-guided ride to some of Skagway's best sites! You will visit a waterfall, scenic... More
Private Tour
Likely to Sell Out Skagway Trail and Sail
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North America
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Superb8 reviews4.8
This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike E....
Private Tour
Los Cabos Sunset Sailing Adventure
Experience a breathtaking sunset sail on the Cabo San Lucas Bay aboard a luxury catamaran, complete with delicious appetizers and an international open bar. After being picked up from your hotel, embark from the Cabo San Lucas Mar... More
Private Tour
Likely to Sell Out Los Cabos Sunset Sailing Adventure
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North America
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Exellent2 reviews4.5
Experience a breathtaking sunset sail on the Cabo San Lucas Bay aboard a luxury catamaran, complete ....
Private Tour
Key West Sail and Snorkel Day Trip from Fort Lauderdale
Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from Fort Lauderdale promises thrilling experiences and breathtaking sights both above and ... More
Private Tour
Likely to Sell Out Key West Sail and Snorkel Day Trip from Fort Lauderdale
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North America
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Good16 reviews3.1
Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it....
Private Tour
Snorkeling and Catamaran Cruise to Isla Mujeres with Lunch
Set sail on an unforgettable day aboard the Star Blue Catamaran from Marina Flamingos in Cancún. Enjoy a premium national open bar while sailing to Isla Mujeres, where you can explore the stunning Playa Norte and spend free time ... More
Private Tour
Likely to Sell Out Snorkeling and Catamaran Cruise to Isla Mujeres with Lunch
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North America
Set sail on an unforgettable day aboard the Star Blue Catamaran from Marina Flamingos in Cancún. En....
Private Tour
Exciting Public Afternoon Sail in Hilton Head
Looking for a more personal sailing experience without booking an entire private charter? The Afternoon Public Sail is the perfect balance. With a maximum of just six guests onboard, you’ll enjoy an intimate, relaxed atmosphere.... More
Private Tour
Likely to Sell Out Exciting Public Afternoon Sail in Hilton Head
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North America
Looking for a more personal sailing experience without booking an entire private charter? The Aftern....
Private Tour
2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests)
This is a "Private Charter" Sailing Experience on San Francisco Bay for up to 6 guests, with a USCG licensed captain and crew where you'll sail past the Golden Gate Bridge, Alcatraz and Angel Islands and across the San Francisco w... More
Private Tour
Likely to Sell Out 2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests)
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North America
This is a "Private Charter" Sailing Experience on San Francisco Bay for up to 6 guests, with a USCG ....
Private Tour
Private Morning Sail, Dolphin and History Tour on Mystique
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. For over 12 years, our sailing yachts are the highest quality and operated by two professional ... More
Private Tour
Likely to Sell Out Private Morning Sail, Dolphin and History Tour on Mystique
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North America
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Superb85 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound
Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these waters back in 1792. From Seattle’s Shilshole Bay Marina we sail west across Puget Sound toward the magnificent Olympic Mountains. A... More
Private Tour
Likely to Sell Out Mid-Day & Sunset Sailing on Seattle's Majestic Puget Sound
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North America
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Superb34 reviews5
Experience the magic of being carried by the wind, just as Peter Puget was when he mapped these wate....
Private Tour