Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 769 Sailing Trips activities in North America. Sort by Popularity.Miami Millionaires Sightseeing Cruise
Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmerizing beauty of Biscayne Bay, while getting an exclusive glimpse into the luxurious lifestyle of Miami's elite, with a bilingual com... More
Miami Millionaires Sightseeing Cruise
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North America
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Exellent1,902 reviews4.3
Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time
Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboard a spacious sailing catamaran. This family-friendly adventure includes approximately 1 hour of snorkeling at Shell Island, where... More
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....
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North America
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Superb4,849 reviews4.9
Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboa....
Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure
There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to se... More
Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure
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North America
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Superb595 reviews4.7
There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....
San Francisco Bay Cruise
You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour excursion heads underneath the Golden Gate Bridge, around Alcatraz Island, past Angel Island State Park, and alongside the city's... More
San Francisco Bay Cruise
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North America
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Exellent384 reviews4.4
You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour....
Evening Colors Sunset Sail Tour in Seattle
Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hoist the sails, then we will shut the engine down and enjoy the quiet of our beautiful schooner cutting through the tranquil Puget So... More
Likely to Sell Out Evening Colors Sunset Sail Tour in Seattle
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North America
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Superb660 reviews4.8
Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....
Kona Signature Catamaran Sunset Sail
End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean and coastline as the sky transforms with vibrant hues of orange, pink and gold. Relax on d... More
Likely to Sell Out Kona Signature Catamaran Sunset Sail
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North America
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Superb297 reviews4.8
End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....
Waikiki: 2-hour Turtle Canyon Snorkeling Adventure
Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard our either 55-ft open-style catamaran or 50-ft double-decker power catamaran and ... More
Likely to Sell Out Waikiki: 2-hour Turtle Canyon Snorkeling Adventure
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North America
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Superb1,485 reviews4.7
Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cr....
Los Cabos Luxury Sailing, Snorkel and Lunch Cruise
Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time to hang out in the pristine water and take it easy aboard the sailboat – you can snorkel with tropical fish, stand atop a paddleb... More
Likely to Sell Out Los Cabos Luxury Sailing, Snorkel and Lunch Cruise
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North America
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Superb3,769 reviews4.8
Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time t....
Isla Mujeres Luxury Sailing: Adults Only or Family Friendly
Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — with the option to choose between an Adults Only or Family Friendly experience. Snorkel in warm, crystalline waters, then savor a del... More
Likely to Sell Out Isla Mujeres Luxury Sailing: Adults Only or Family Friendly
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North America
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Superb3,550 reviews4.6
Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — wit....
Seattle Sailing Harbor Tour
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way to see the Seattle skyline, the beauty of the Puget Sound, even mountain views! We ... More
Likely to Sell Out Seattle Sailing Harbor Tour
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North America
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Superb517 reviews4.7
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....
Classic Tall Ship Cruise in Boston Harbor
Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liberty Star or Fame. Get away from the hustle and bustle of the city streets and enjoy some quality time out on the water with unbeata... More
Likely to Sell Out Classic Tall Ship Cruise in Boston Harbor
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North America
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Superb718 reviews4.7
Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liber....
Pirate Ship Sunset Dinner and Show in Los Cabos
Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic sunset cruise with a show that is the joy for children and grown-ups alike. Our pirates, dance, chant, climb the ropes, while you... More
Likely to Sell Out Pirate Ship Sunset Dinner and Show in Los Cabos
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North America
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Exellent745 reviews4.3
Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic ....
Key West Signature Sunset Sail with Live Music, Open Bar & Food
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More
Likely to Sell Out Key West Signature Sunset Sail with Live Music, Open Bar & Food
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North America
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Exellent386 reviews4.5
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....
Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience offers breathtaking views of the sunset complemented by deligh... More
Likely to Sell Out Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
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North America
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Superb62 reviews4.6
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....
Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
Award Winning Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip. Enjoy Cozumel's top attractions and most visited reefs in the Caribbean... More
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Likely to Sell Out Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
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North America
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Exellent1,591 reviews4.3
Award Winning Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Specta....
Free Cancellation
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Likely to Sell Out
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki. Swim alongside Hawaiian green sea turtles and vibrant tropical fis... More
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Likely to Sell Out Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
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North America
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Superb1,712 reviews4.9
Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour....
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Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor
Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall Ship for a unique sailing experience. There is no better way to witness all o... More
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Likely to Sell Out Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....
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North America
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Exellent775 reviews4.5
Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....
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Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and fea... More
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Likely to Sell Out Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
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North America
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Superb3,787 reviews4.7
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....
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Dolphin Sunset Cruise in Panama City Beach on the "Island Time"
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More
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Likely to Sell Out Dolphin Sunset Cruise in Panama City Beach on the "Island Time"
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North America
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Superb2,045 reviews4.9
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....
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Cabo Boat Ride to El Arco & Lover’s Beach with Swimming
Enjoy the perfect combination of sightseeing and beach time on this Cabo San Lucas boat ride to El Arco and Lover’s Beach. Cruise along the stunning coastline as you pass iconic landmarks like the Arch, Sea Lion Colony, and Peli... More
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Likely to Sell Out Cabo Boat Ride to El Arco & Lover’s Beach with Swimming
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North America
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Superb481 reviews4.6
Enjoy the perfect combination of sightseeing and beach time on this Cabo San Lucas boat ride to El A....
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