Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 766 Sailing Trips activities in North America. Sort by Popularity.Miami Millionaires Sightseeing Cruise
Navigate through the beautiful waters and be captivated by the panoramic views of Miami's skyline, the vibrant Port of Miami, the secluded Fisher Island, and the sun-kissed shores of Miami Beach. Witness the opulent mansions of Mi... More
Miami Millionaires Sightseeing Cruise
-
North America
-
Exellent1,997 reviews4.3
Navigate through the beautiful waters and be captivated by the panoramic views of Miami's skyline, t....
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....
-
North America
-
Superb4,979 reviews4.9
Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboa....
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
Free Cancellation
(Saving 10% )
Kona Signature Catamaran Sunset Sail
-
North America
-
Superb327 reviews4.8
End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....
Free Cancellation
(Saving 10% )
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
Free Cancellation
(Saving inf% )
San Francisco Bay Cruise
-
North America
-
Exellent407 reviews4.4
You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour....
Free Cancellation
(Saving inf% )
Waikiki 2 Hour Sunset Sailing Catamaran Swim and 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
Free Cancellation
(Saving inf% )
Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure
-
North America
-
Superb614 reviews4.7
There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....
Free Cancellation
(Saving inf% )
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup
Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP), sea scooters, and more—offeri... More
Free Cancellation
(Saving inf% )
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup
-
North America
-
Superb377 reviews4.9
Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamara....
Free Cancellation
(Saving inf% )
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
Free Cancellation
(Saving inf% )
Classic Tall Ship Cruise in Boston Harbor
-
North America
-
Superb786 reviews4.7
Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liber....
Free Cancellation
(Saving inf% )
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
Free Cancellation
(Saving inf% )
Los Cabos Luxury Sailing, Snorkel and Lunch Cruise
-
North America
-
Superb3,821 reviews4.8
Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time t....
Free Cancellation
(Saving inf% )
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
Free Cancellation
(Saving 5% )
Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
-
North America
-
Exellent1,615 reviews4.3
Award Winning Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Specta....
Free Cancellation
(Saving 5% )
2 Hour Sailing Cruise on Lake Tahoe
Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing adventure and include complementary local beer and wine, as well as non-alcoholic beverages on all of our daily cruises. Unlike other t... More
Free Cancellation
(Saving inf% )
2 Hour Sailing Cruise on Lake Tahoe
-
North America
-
Superb1,001 reviews4.9
Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing advent....
Free Cancellation
(Saving inf% )
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
Free Cancellation
(Saving inf% )
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
-
North America
-
Superb1,772 reviews4.9
Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour....
Free Cancellation
(Saving inf% )
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
Free Cancellation
(Saving inf% )
Waikiki: 2-hour Turtle Canyon Snorkeling Adventure
-
North America
-
Superb1,509 reviews4.7
Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cr....
Free Cancellation
(Saving inf% )
Waikiki Sunset Cocktail Sail on the Moana Catamaran
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More
Free Cancellation
(Saving inf% )
Waikiki Sunset Cocktail Sail on the Moana Catamaran
-
North America
-
Superb2,396 reviews4.9
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....
Free Cancellation
(Saving inf% )
1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain
Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises.... More
Free Cancellation
(Saving inf% )
1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain
-
North America
-
Exellent710 reviews4.1
Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....
Free Cancellation
(Saving inf% )
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
Free Cancellation
(Saving inf% )
Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
-
North America
-
Superb78 reviews4.6
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....
Free Cancellation
(Saving inf% )
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
Free Cancellation
(Saving inf% )
Isla Mujeres Luxury Sailing: Adults Only or Family Friendly
-
North America
-
Superb3,598 reviews4.6
Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — wit....
Free Cancellation
(Saving inf% )
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
Free Cancellation
(Saving inf% )
Evening Colors Sunset Sail Tour in Seattle
-
North America
-
Superb702 reviews4.8
Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....
Free Cancellation
(Saving inf% )
City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour
Discover the best of San Diego Bay on our expertly narrated harbor tour. Spanning over 13 miles, this journey takes you past iconic landmarks such as Seaport Village, Shelter Island, and the ship-building docks. Gaze at the scenic... More
Free Cancellation
(Saving inf% )
City Cruises San Diego: Scenic 90-Minute Narrated Harbor Tour
-
North America
-
Exellent563 reviews4.5
Discover the best of San Diego Bay on our expertly narrated harbor tour. Spanning over 13 miles, thi....
Free Cancellation
(Saving inf% )
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
Free Cancellation
(Saving inf% )
Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
-
North America
-
Superb3,833 reviews4.7
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....
Free Cancellation
(Saving inf% )
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
Free Cancellation
(Saving inf% )
Seattle Sailing Harbor Tour
-
North America
-
Superb564 reviews4.7
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....
Free Cancellation
(Saving inf% )