Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 672 Sailing Trips activities in North America. Sort by Popularity. - Page 10Windjammer Classic Sunset Sail from Camden, Maine
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More

Windjammer Classic Sunset Sail from Camden, Maine
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North America
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Superb332 reviews4.9
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....
Statue of Liberty Sunset Cruise and New York City Sky Line
New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View of the Manhattan skyline, One World Trade Center and the Empire State Building.Enjoy a panoramic view of lower Manhattan as you p... More

Statue of Liberty Sunset Cruise and New York City Sky Line
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North America
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Good38 reviews3.1
New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View....
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands... More

Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
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North America
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Superb46 reviews5
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....
Sailing Tour through the Laguna de los Siete Colores
Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, being your best option to know this magical place without damaging the ecosystem. Guided by a team of professionals, with whom you ... More

Sailing Tour through the Laguna de los Siete Colores
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North America
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Superb1,342 reviews5
Wild Wave Bacalar is a company committed to caring for the environment. Our trips are by sailboat, b....
Reef Snorkel, underwater adventure in Puerto Morelos With Transportation & Lunch
Snorkel activity in a caribbean reef. Amazing sightseeing and shore excursion. This is consider a must activity in Cancun. You will visit one of the most bigger reef in the world, this is consider as the 2nd one worldwide. Imagi... More

Reef Snorkel, underwater adventure in Puerto Morelos With Transpo....
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North America
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Very Good3 reviews4
Snorkel activity in a caribbean reef. Amazing sightseeing and shore excursion. This is consider a mu....
Sunset Sail Cruise in Key West
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More

Sunset Sail Cruise in Key West
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North America
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Superb219 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....
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 adve... More

Afternoon Sail & Snorkel to the Captain Cook Monument
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North America
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Superb226 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....
Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport
Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and family to see all the iconic waterfront sights of Newport and Narraganset... More

Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport
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North America
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Superb12 reviews4.6
Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard ....
Afternoon 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. We wi... More

Afternoon Half-Day Catmaran Sailing and Snorkel Adventure
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North America
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Exellent70 reviews4.5
Want to enjoy a sailing tour, where you can snorkel and visit Isla Mujeres in just half a day? This ....
Private Charleston Harbor Catamaran Sail
Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a panoramic view with large sliding glass doors between the saloon and the rear deck space, with... More
Private Tour

Private Charleston Harbor Catamaran Sail
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North America
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Superb26 reviews5
Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing cata....
Private Tour
Tour to Arch in the Clear Boat Cruise Ship Terminal Hotel PICKUP!
Enjoy the most popular experience in Cabo in our 100% transparent boat! A unique experience in the world where you will get to know the famous arch, the incredible rock formations, tropical fish, reefs, the love and divorce beach,... More
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Private Tour

Tour to Arch in the Clear Boat Cruise Ship Terminal Hotel PICKUP!
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North America
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Superb5 reviews4.8
Enjoy the most popular experience in Cabo in our 100% transparent boat! A unique experience in the w....
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Private Tour
Tall Ship Silva Sailing Cruise
A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Halifax Harbour. Join us on our comfortable and thoroughly impressive vessel for this relaxing afternoon outing on the water. Your j... More
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Private Tour

Tall Ship Silva Sailing Cruise
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North America
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Exellent203 reviews4.1
A cruise aboard The Tall Ship Silva is the perfect way to fully appreciate a beautiful day on the Ha....
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Private Tour
Tour to The Arch and Lover's Beach (optional) from Cabo
This is a tour in a boat that will take you to Divorce Beach, Lover's Beach, the Arch, Land's End, and through the Marina. See it all in one tour! During this awesome experience, you will be able to see a great variety of tropical... More
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Private Tour

Tour to The Arch and Lover's Beach (optional) from Cabo
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North America
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Superb4 reviews5
This is a tour in a boat that will take you to Divorce Beach, Lover's Beach, the Arch, Land's End, a....
Skip The Line
Private Tour
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
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Private Tour

Full-Day Private Sailing Cruise Puerto Vallarta with Snorkeling
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North America
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Superb107 reviews4.9
Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Va....
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Private Tour
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
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Private Tour

Private Catamaran Charter in Waikiki (7-12 Guests)
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North America
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Superb107 reviews4.9
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....
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Private Tour
All Inclusive Tulum: 4 hrs Private in 40' Catamaran Bali
It is an incredible and unique experiences because for 4 hours you will be the owner of this incredible sailing catamaran, with a host and a chef at your disposal, the captain will take you to sail in the most beautiful waters of ... More
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Private Tour

All Inclusive Tulum: 4 hrs Private in 40' Catamaran Bali
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North America
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Superb278 reviews5
It is an incredible and unique experiences because for 4 hours you will be the owner of this incredi....
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Private Tour
Private Morning Sailing/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
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Private Tour

Private Morning Sailing/Dolphin & History Tours on 43ft Mystique
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North America
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Superb72 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
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Private Tour
Private sailing tour of Bacalar Lagoon
Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a delicious fruit cocktail, water and beer. Our certified guides will make this tour an unfo... More
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Private Tour

Private sailing tour of Bacalar Lagoon
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North America
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Superb297 reviews5
Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper ....
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Private Tour
6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beaches
Sail on a private trip aboard our 50-foot private yacht, 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 you to make... More
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Private Tour

6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beac....
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North America
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Superb12 reviews5
Sail on a private trip aboard our 50-foot private yacht, ideal for up to 18 passengers. We are sure ....
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Private Tour
Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay
We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment to sustainability and having a minimal impact on the environment ! It is a wholesome adventure that will le... More
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Private Tour

Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay
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North America
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Superb10 reviews4.9
We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We ....
Skip The Line
Private Tour