Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 727 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
Likely to Sell Out Miami Millionaires Sightseeing Cruise
-
North America
-
Exellent1,403 reviews4.3
Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....
2-Hour Whale Watching of Waikiki, Oahu: Guaranteed Sightings
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More
Likely to Sell Out 2-Hour Whale Watching of Waikiki, Oahu: Guaranteed Sightings
-
North America
-
Superb972 reviews4.6
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....
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
-
Superb3,401 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
-
Superb3,506 reviews4.7
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand K... More
Likely to Sell Out Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
-
North America
-
Superb787 reviews4.9
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....
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
-
Superb1,360 reviews4.9
Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu catamaran snorkel tour....
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy ... More
Likely to Sell Out Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
-
North America
-
Superb1,345 reviews4.9
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....
Likely to Sell Out
Turtle Canyon Snorkel from Waikiki
**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join us for a **2-hour snorkeling adventure** at **Turtle Canyon**, one of Oahu’s top snorkeling spots! Cruise along the stunning **W... More
Free Cancellation
(Saving 15% )
Likely to Sell Out Turtle Canyon Snorkel from Waikiki
-
North America
-
Superb1,258 reviews4.7
**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join ....
Free Cancellation
(Saving 15% )
Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
Award Winning Cozumel 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 C... More
Free Cancellation
(Saving 5% )
Likely to Sell Out Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
-
North America
-
Exellent1,449 reviews4.3
Award Winning Cozumel Snorkeling Trip! Set off for a great Adventure to the Caribbean and admire th....
Free Cancellation
(Saving 5% )
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast
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 Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast
-
North America
-
Superb2,188 reviews4.9
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....
Likely to Sell Out
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
Free Cancellation
(Saving 10% )
Likely to Sell Out Pirate Ship Sunset Dinner and Show in Los Cabos
-
North America
-
Exellent641 reviews4.3
Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic ....
Free Cancellation
(Saving 10% )
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
-
North America
-
Superb206 reviews4.8
End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....
Waikiki Turtle Snorkel and Sail on Hawea Catamaran
Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island relaxation in one extraordinary outing. Swim among sea turtles and tropical fi... More
Likely to Sell Out Waikiki Turtle Snorkel and Sail on Hawea Catamaran
-
North America
-
Superb1,639 reviews4.8
Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This pop....
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty of interesting whale information Convenient location walking... More
Likely to Sell Out Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
-
North America
-
Superb166 reviews4.7
Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....
Key West's Favorite Afternoon Dolphin Sail
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More
Likely to Sell Out Key West's Favorite Afternoon Dolphin Sail
-
North America
-
Superb121 reviews4.6
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....
Key West Reef Morning Snorkeling with Breakfast and Mimosas
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More
Likely to Sell Out Key West Reef Morning Snorkeling with Breakfast and Mimosas
-
North America
-
Exellent579 reviews4.5
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....
Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef
Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quality, comfort, and performance. Live the yachting lifestyle, walk barefoot on the deck, feel the sun and breeze on your face, dance ... More
Likely to Sell Out Cabo San Lucas Luxury Sailing Yacht and Dinner with a Chef
-
North America
-
Exellent285 reviews4.5
Sail into the sunset on board Tu Enamorado, a beautifully crafted sailing yacht of unsurpassed quali....
Waikiki Sunset Whale Watching Cruise: Guaranteed Whale Sightings
Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden hues of the evening sky, where you'll have the chance to witness majestic whal... More
Likely to Sell Out Waikiki Sunset Whale Watching Cruise: Guaranteed Whale Sightings
-
North America
-
Exellent72 reviews4.4
Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an u....
Waikoloa Signature Catamaran Sunset Sail
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More
Likely to Sell Out Waikoloa Signature Catamaran Sunset Sail
-
North America
-
Superb393 reviews4.7
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....
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
-
Superb97 reviews4.8
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....