Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 723 Sailing Trips activities in North America. Sort by Popularity. - Page 262 hours - Shared Sunset Sail along Historic St Augustine Bayfront
We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory. This 2-hour sail gives passengers a ... More
2 hours - Shared Sunset Sail along Historic St Augustine Bayfront
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North America
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Superb7 reviews4.7
We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our sta....
New York Fall Foliage Sail up the Hudson River
Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Schooner America 2.0, both 1800s-style sailboats. Bordering the Hudson River north of Fort Lee, New Jersey, the Palisade Cliffs are am... More
Likely to Sell Out New York Fall Foliage Sail up the Hudson River
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North America
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Exellent11 reviews4.5
Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Scho....
Private Sail Around New York City and The Statue of Liberty
Discover NYC from a completely different perspective on a private sailboat charter. You and your group will view New York City in ways that are breath taking. See the Statue of Liberty up close like you can almost touch it. Sit ba... More
Private Tour
Likely to Sell Out Private Sail Around New York City and The Statue of Liberty
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North America
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Superb7 reviews5
Discover NYC from a completely different perspective on a private sailboat charter. You and your gro....
Private Tour
2-Hour Rosé Luxury Day Sail
This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expert captains leading the way. Keep an eye out for dolphins, seabirds, and Lowcountry landmarks as you relax, unwind, and enjoy the ... More
Private Tour
Likely to Sell Out 2-Hour Rosé Luxury Day Sail
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North America
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Superb1 review5
This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expe....
Private Tour
Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii
Welcome to the only place in Hawaii where the spirit of ancient Hawaiian seafaring meets modern expectations on the pristine waters of the Kona coast. Immerse yourself in a unique and unforgettable experience as we invite you to j... More
Private Tour
Likely to Sell Out Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii
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North America
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Superb9 reviews4.9
Welcome to the only place in Hawaii where the spirit of ancient Hawaiian seafaring meets modern expe....
Private Tour
Top Tour Sail To Isla Mujeres By Catamaran Buffet And Drinks Included
Stop looking for the perfect tour to Isla mujeres, we are the best option. Why? With us you´ll have: 1.No long lines, direct access 2.Quality food 3.Quality drinks 4.Best Service 5.We will take you to special reefs where on... More
Private Tour
Likely to Sell Out Top Tour Sail To Isla Mujeres By Catamaran Buffet And Drinks Incl....
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North America
Stop looking for the perfect tour to Isla mujeres, we are the best option. Why? With us you´ll hav....
Private Tour
Cabo Catamaran Tour: Snorkeling & Unlimited Drinks Included
Discover the magic of Cabo San Lucas on this exhilarating catamaran cruise! Glide across the sparkling waters of the Pacific Ocean and the Sea of Cortez, where you’ll have the chance to snorkel and explore vibrant underwater lif... More
Private Tour
Likely to Sell Out Cabo Catamaran Tour: Snorkeling & Unlimited Drinks Included
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North America
Discover the magic of Cabo San Lucas on this exhilarating catamaran cruise! Glide across the sparkli....
Private Tour
Cancun Half Day Sailing Cataman Cruise to Isla Mujeres
Original Half Day Sailing since 2012, No need to invest your whole day to visit Isla Mujeres! Lite Tour to Isla Mujeres provides full sailing, snorkeling & enough time to visit Isla Mujeres for shopping or just enjoy this wonderf... More
Private Tour
Likely to Sell Out Cancun Half Day Sailing Cataman Cruise to Isla Mujeres
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North America
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Superb1 review5
Original Half Day Sailing since 2012, No need to invest your whole day to visit Isla Mujeres! Lite ....
Private Tour
Private Catamaran: Snorkel, Swim and Dolphin Watching
Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take you to some of the best spots the area has to offer while you are visiting the Emerald Coast. ... More
Private Tour
Likely to Sell Out Private Catamaran: Snorkel, Swim and Dolphin Watching
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North America
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Superb1 review5
Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion....
Private Tour
2 - Hour Private Hilton Head Morning Dolphin Watching / Sail
This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side of the island - generally best conditions for sailing). During the MORNING, this is generally a calm - light wind relaxing sail, a... More
Private Tour
Likely to Sell Out 2 - Hour Private Hilton Head Morning Dolphin Watching / Sail
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North America
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Superb33 reviews5
This 2 hour Private Morning Sailing tour, the Captain will take you to Port Royal Sound (North side ....
Private Tour
Shared Day Sail along Historic St Augustine Bayfront
Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories on the sea. Our cruise is perfect for all water-lovers: families, couples, and friends. Some guests interact with the USCG licensed... More
Private Tour
Likely to Sell Out Shared Day Sail along Historic St Augustine Bayfront
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North America
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Superb6 reviews5
Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories o....
Private Tour
Private Whale Watching Sailing Adventure
From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback whales. Departing near Waikiki, enjoy a leisurely sail against the majestic backdrop of Diamond Head as you scan the water for maj... More
Private Tour
Likely to Sell Out Private Whale Watching Sailing Adventure
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North America
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Good2 reviews3.5
From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback ....
Private Tour
Yo Ho Pirate Show at Sunset, Dinner and Legends on the High Seas
Go back in time, to the days when Cabo was home to pirates A fantastic sunset cruise with a show which is the joy of children and adults alike. Our pirates dance, sing, climb the ropes, while you enjoy the beautiful sunset and li... More
Private Tour
Likely to Sell Out Yo Ho Pirate Show at Sunset, Dinner and Legends on the High Seas
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North America
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Superb1 review5
Go back in time, to the days when Cabo was home to pirates A fantastic sunset cruise with a show whi....
Private Tour
Likely to Sell Out Explore Turtle Canyons Waikiki Snorkel and Sail Adventure
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North America
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Exellent4 reviews4.5
Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience ....
Private Tour
Private Cabo San Lucas Sunset Cruise on 33´ sailboat
You will enjoy watching the sun set on the horizon from your very own private boat with our accommodating and knowledgeable crew. Every tour includes sightseeing along the spectacular Finisterra Rocky point where you will see the ... More
Private Tour
Likely to Sell Out Private Cabo San Lucas Sunset Cruise on 33´ sailboat
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North America
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Superb61 reviews4.9
You will enjoy watching the sun set on the horizon from your very own private boat with our accommod....
Private Tour
Sunset Cruise Tequila Tasting
Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the history of one of Mexico's most iconic drinks, brought to you by Tequila Cabo Único and Sunrider. You'll get to know the iconic Cabo S... More
Private Tour
Likely to Sell Out Sunset Cruise Tequila Tasting
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North America
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Superb4 reviews5
Join us for a one-of-a-kind Sunset Sailboat & Tequila tasting in Cabo San Lucas! Discover the histo....
Private Tour
Sailing Charter
Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend out of scenic Sequim Bay! Ingrid Princess is an ocean going, full keel ketch avail... More
Private Tour
Likely to Sell Out Sailing Charter
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North America
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Superb5 reviews5
Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make a....
Private Tour
Guided Tour of Puerto Morelos Reefs with Snorkeling Experience
Welcome to an incredible adventure, if what you like is getting to know new places and being in contact with nature, then this activity is for you. We will take you to know the second largest coral reef in the world, the first one... More
Private Tour
Likely to Sell Out Guided Tour of Puerto Morelos Reefs with Snorkeling Experience
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North America
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Very Good3 reviews4
Welcome to an incredible adventure, if what you like is getting to know new places and being in cont....
Private Tour
Private Cancun Sailboat Cruise with Beers and Sodas Included
Escape to paradise with our exclusive private sailing boat cruise to Isla Mujeres, a pristine island gem just off the coast of Cancun. Step aboard our fine vessel and embark on a journey of discovery and relaxation in the breathta... More
Private Tour
Likely to Sell Out Private Cancun Sailboat Cruise with Beers and Sodas Included
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North America
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Superb1 review5
Escape to paradise with our exclusive private sailing boat cruise to Isla Mujeres, a pristine island....
Private Tour
SUNSET CRUISE in Key Largo,FL.
KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting in long lines. Personalize the trip to your liking. A private charter makes it more personab... More
Private Tour
Likely to Sell Out SUNSET CRUISE in Key Largo,FL.
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North America
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Superb3 reviews5
KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need t....
Private Tour