Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 20Clear 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
Clear Boat to Cabo Lands End, The Arch and more
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North America
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Exellent17 reviews4.5
Are you ready for an unforgettable experience? Come to visit the spectacular sea of Los Cabos, most ....
Pirate Ship Premium Dinner Cruise with Show
While visiting Puerto Vallarta is a must to take the Pirate Sailboat tour. Enjoying magnificent views of Banderas Bay, take unforgettable photos of this amazing experience, while you taste a delicious dinner and have a good time ... More
Pirate Ship Premium Dinner Cruise with Show
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North America
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Exellent34 reviews4.4
While visiting Puerto Vallarta is a must to take the Pirate Sailboat tour. Enjoying magnificent vie....
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
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....
All Inclusive Full Day and Sunset Private Catamaran in St. Pete
Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks,... More
Private Tour
Likely to Sell Out All Inclusive Full Day and Sunset Private Catamaran in St. Pete
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North America
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Very Good3 reviews4
Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and cr....
Private Tour
Bacalar Private Sailing Tour : cervezas & Snack with Pickup
Discover Bacalar Lagoon like no other tour. Our experiences are responsibly crafted to offer a truly unique adventure. Visit hidden, less-explored spots and enjoy the lagoon with skilled captains and crew fluent in Spanish, Englis... More
Private Tour
Likely to Sell Out Bacalar Private Sailing Tour : cervezas & Snack with Pickup
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North America
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Superb20 reviews5
Discover Bacalar Lagoon like no other tour. Our experiences are responsibly crafted to offer a truly....
Private Tour
Captain Steve's Sailing Experience on Long Island
Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best enjoyed from the water. With Captain Steve's Sailing Experience, you can experience the beauty of the area from a unique perspecti... More
Private Tour
Likely to Sell Out Captain Steve's Sailing Experience on Long Island
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North America
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Superb11 reviews5
Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best ....
Private Tour
Afternoon Ali'i Adventure
Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More
Private Tour
Likely to Sell Out Afternoon Ali'i Adventure
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North America
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Superb6 reviews5
Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....
Private Tour
Likely to Sell Out
Polynesian Canoe Sunset Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and bec... More
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Likely to Sell Out Polynesian Canoe Sunset Sail
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North America
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Superb127 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) off....
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Private Tour
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Likely to Sell Out
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in the picturesque views of St. Michaels, MD. Your journey includes gliding throu... More
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Likely to Sell Out 2-Hour Relaxing Chesapeake Day Sail on Lady Patty
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North America
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Superb6 reviews5
Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise of....
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Los Cabos Private Catamaran Sunset Cruise with Snacks & Open Bar
Experience Cabo San Lucas like never before on your private catamaran at sunset. Unlike crowded group tours, this 2-hour cruise is exclusive to your party, giving you space to relax, celebrate, and enjoy the views in privacy. Sai... More
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Likely to Sell Out Los Cabos Private Catamaran Sunset Cruise with Snacks & Open Bar
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North America
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Superb1 review5
Experience Cabo San Lucas like never before on your private catamaran at sunset. Unlike crowded grou....
Free Cancellation
Private Tour
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Private Hilton Head Sunset Sailing Tour with Dolphin Watching
This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound (North side of island - generally best conditions for sailing). During Sunset, This is generally still pretty breezy with some goo... More
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Likely to Sell Out Private Hilton Head Sunset Sailing Tour with Dolphin Watching
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North America
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Superb125 reviews5
This 2 hour Private Sunset Sail, the Captain will take you (and up to 6 people) to Port Royal Sound ....
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Fort Lauderdale Sailing Charter
Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a beautiful blend of natural mangroves, luxurious waterfront homes, and ... More
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Likely to Sell Out Fort Lauderdale Sailing Charter
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North America
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Superb401 reviews5
Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called....
Free Cancellation
Private Tour
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Key West Champagne Sunset Sail with Drinks and Hors d Oeuvres
Experience the magic of a Key West sunset from the water on this elegant 2-hour sailing cruise departing from the historic Key West Seaport. As the sails are raised and the breeze carries you across the sparkling Gulf waters, unwi... More
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Likely to Sell Out Key West Champagne Sunset Sail with Drinks and Hors d Oeuvres
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North America
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Superb401 reviews5
Experience the magic of a Key West sunset from the water on this elegant 2-hour sailing cruise depar....
Free Cancellation
Private Tour
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2 Hour Sailing Lesson in Wrightsville Beach
Experience the thrill of sailing a 26' performance keelboat! Our knowledgeable captains will take you around the waterways of Wrightsville Beach and out into the Atlantic Ocean. You have the freedom to make this a learning experie... More
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Likely to Sell Out 2 Hour Sailing Lesson in Wrightsville Beach
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North America
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Superb8 reviews5
Experience the thrill of sailing a 26' performance keelboat! Our knowledgeable captains will take yo....
Free Cancellation
Private Tour
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Whale Watching Sailboat Tour in San Jose del Cabo
Join us at the marina for a brief orientation before boarding the vessel. As we set sail, you'll cruise past the iconic landmarks of San José del Cabo. Like the Estuary a bird sanctuary and the amazing coastline of the Sea of Cor... More
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Likely to Sell Out Whale Watching Sailboat Tour in San Jose del Cabo
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North America
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Superb3 reviews5
Join us at the marina for a brief orientation before boarding the vessel. As we set sail, you'll cru....
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Old Plank Adventures: Sail into Deep Tranquility
Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, delivering gourmet 5-star experiences on the sparkling waters of Santa Monica Bay and beyond. Founded by Captain & Chef Matthew Manc... More
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Likely to Sell Out Old Plank Adventures: Sail into Deep Tranquility
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North America
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Superb2 reviews5
Old Plank Sailing Adventures is a boutique luxury sailing charter and aquatic expedition company, de....
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Afternoon Sail With the Whales from Lahaina Harbor
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More
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Likely to Sell Out Afternoon Sail With the Whales from Lahaina Harbor
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North America
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Superb1 review5
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
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Private Tour
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Sunset Yacht Cruise | Champagne Included | San Diego Bay
What makes this experience truly special is the blend of refined European luxury and a relaxed, intimate atmosphere without the feel of a large group tour. You will be sailing aboard a beautifully crafted French yacht designed for... More
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Likely to Sell Out Sunset Yacht Cruise | Champagne Included | San Diego Bay
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North America
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Superb1 review5
What makes this experience truly special is the blend of refined European luxury and a relaxed, inti....
Free Cancellation
Private Tour
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Private Sunset Sail in San Diego Up to 6 guests
Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking to experience the bay from the water. Relax while our licensed captain handles... More
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Likely to Sell Out Private Sunset Sail in San Diego Up to 6 guests
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North America
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Superb73 reviews5
Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perf....
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Luxury Snorkel Adventure in Cabo
Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located at Santa Maria Bay or Chileno Bay, at either one of this beach areas is where boat captain will make a stop for snorkeling at one ... More
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Likely to Sell Out Luxury Snorkel Adventure in Cabo
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North America
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Superb57 reviews4.8
Los Cabos enjoys 360 days of sunshine, endless stretches of unsealed sand and a Marine Park located ....
Free Cancellation
Private Tour
(Saving 10% )