Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 714 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
-
Exellent2,076 reviews4.3
Navigate through the beautiful waters and be captivated by the panoramic views of Miami's skyline, t....
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
Kona Signature Catamaran Sunset Sail
-
North America
-
Superb385 reviews4.8
End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....
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
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup
-
North America
-
Superb632 reviews4.9
Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamara....
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
Likely to Sell Out San Francisco Bay Cruise
-
North America
-
Exellent432 reviews4.4
You haven’t fully experienced San Francisco until you’ve taken a Bay Cruise. This popular 1-hour....
Maui Romantic Sunset Sail for Couples with Open Bar & Appetizers
Experience a romantic Maui sunset together aboard Akialoa, a luxury 55-foot sailing catamaran. This two-hour evening sail takes you into the picturesque ʻAuʻau Channel, where you can unwind together as the sun sets over the Paci... More
Likely to Sell Out Maui Romantic Sunset Sail for Couples with Open Bar & Appetizers
-
North America
-
Superb52 reviews4.9
Experience a romantic Maui sunset together aboard Akialoa, a luxury 55-foot sailing catamaran. This ....
Turtles & Tacos Luxury Catamaran Snorkel
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and snorkel alongside Hawaiian green sea turtles and colorful tropical fish at ... More
Likely to Sell Out Turtles & Tacos Luxury Catamaran Snorkel
-
North America
-
Superb176 reviews4.7
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....
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
Likely to Sell Out Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
-
North America
-
Exellent1,638 reviews4.3
Award Winning Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire the Specta....
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
-
North America
-
Superb3,686 reviews4.6
Join us for the Luxury Sailing Adventure to Isla Mujeres aboard a state-of-the-art catamaran — wit....
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
Likely to Sell Out Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
-
North America
-
Superb3,883 reviews4.7
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....
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
-
North America
-
Exellent422 reviews4.5
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....
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
Likely to Sell Out Waikiki Sunset Cocktail Sail on the Moana Catamaran
-
North America
-
Superb2,462 reviews4.9
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....
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
Likely to Sell Out Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
-
North America
-
Superb1,827 reviews4.9
Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour....
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
-
North America
-
Superb3,879 reviews4.8
Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time t....
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look for dolphins, whales, and other marine critters as you sip a drink, snap som... More
Likely to Sell Out Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady
-
North America
-
Superb1,619 reviews4.7
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....
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
Likely to Sell Out Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....
-
North America
-
Superb5,074 reviews4.9
Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboa....
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
-
North America
-
Exellent780 reviews4.3
Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic ....
Snorkel Sail Adventure off Ka'anapali Beach in Maui
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More
Likely to Sell Out Snorkel Sail Adventure off Ka'anapali Beach in Maui
-
North America
-
Superb55 reviews5
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....
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
Likely to Sell Out Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....
-
North America
-
Exellent848 reviews4.5
Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....
Lahaina Maui Sunset Sail on 'Alihilani
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands from the... More
Likely to Sell Out Lahaina Maui Sunset Sail on 'Alihilani
-
North America
-
Superb225 reviews4.9
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....
Waikiki Sunset Boat Cruise
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More
Likely to Sell Out Waikiki Sunset Boat Cruise
-
North America
-
Superb273 reviews4.9
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....