Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 7Private Sailing Charter with Captain, BYOB
Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More
Private Tour
Likely to Sell Out Private Sailing Charter with Captain, BYOB
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North America
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Superb65 reviews5
Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6....
Private Tour
Sunset Dolphin Sail Aboard the Footloose Catamaran
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More
Private Tour
Likely to Sell Out Sunset Dolphin Sail Aboard the Footloose Catamaran
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North America
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Superb443 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
Private Tour
Key West Private Charter: Sandbar and Snorkeling
This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a formal, guided eco-tour, this trip offers a more laid-back vibe, allowing you t... More
Private Tour
Likely to Sell Out Key West Private Charter: Sandbar and Snorkeling
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North America
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Superb9 reviews5
This private charter is designed for a relaxed, flexible day on the water, perfect for groups who wa....
Private Tour
Small Group Waikiki Sunset Sailing Tour
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More
Private Tour
Likely to Sell Out Small Group Waikiki Sunset Sailing Tour
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North America
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Superb111 reviews4.9
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....
Private Tour
Whale Tale Adventures in Los cabos
Whale watching is a magical experience for all ages. Seeing the gray whale, known for its long migration and friendly nature, or the majestic humpback whale, famous for its powerful breaches and haunting songs, is unforgettable. T... More
Private Tour
Likely to Sell Out Whale Tale Adventures in Los cabos
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North America
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Superb14 reviews4.6
Whale watching is a magical experience for all ages. Seeing the gray whale, known for its long migra....
Private Tour
4-Hour Fort Lauderdale Sailing Charter
Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More
Private Tour
Likely to Sell Out 4-Hour Fort Lauderdale Sailing Charter
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North America
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Superb314 reviews4.9
Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....
Private Tour
Likely to Sell Out
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More
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Likely to Sell Out Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
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North America
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Superb238 reviews4.9
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....
Free Cancellation
Private Tour
(Saving 30% )
2hr. INTERACTIVE Sailing Experience on San Francisco Bay
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More
Private Tour
Likely to Sell Out 2hr. INTERACTIVE Sailing Experience on San Francisco Bay
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North America
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Superb87 reviews5
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....
Private Tour
Sunset Dolphin Sail Aboard the Privateer Catamaran
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More
Private Tour
Likely to Sell Out Sunset Dolphin Sail Aboard the Privateer Catamaran
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North America
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Superb711 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
Private Tour
Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch
This sailing tour is born of our love of the 7 Colors Lagoon and the desire to share it in an authentic and relaxed way. It’s not just a walk – it’s a space to live together, laugh, toast and connect, whether you come with f... More
Private Tour
Likely to Sell Out Sunset Sailing Tour in Bacalar with Outdoor Bar and Lunch
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North America
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Superb78 reviews4.9
This sailing tour is born of our love of the 7 Colors Lagoon and the desire to share it in an authen....
Private Tour
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral gardens u... More
Private Tour
Likely to Sell Out Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
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North America
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Superb700 reviews5
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....
Private Tour
Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres
Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a delicious drink and the entertainment from the crew. Unique and quality service is our priority. We are sure that you will love all... More
Private Tour
Likely to Sell Out Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres
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North America
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Exellent301 reviews4.4
Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a d....
Private Tour
Private Sailboat + Captain for a Day Experience
RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOICE AWARDS 2022!!! Everyone´s favorite! Enjoy an easy ride around the most relevant landmarks in the lagoon on board of a beautif... More
Private Tour
Likely to Sell Out Private Sailboat + Captain for a Day Experience
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North America
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Superb589 reviews5
RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOI....
Private Tour
Lāna'i Coast Snorkel and Sail
Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as we explore and snorkel the incredible coastline of Maui. Departing daily from 9:30 am - 2:30 pm. We'll check the conditions for t... More
Private Tour
Likely to Sell Out Lāna'i Coast Snorkel and Sail
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North America
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Superb23 reviews5
Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as....
Private Tour
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
Private Tour
Likely to Sell Out 2 Hour Sailing Cruise on Lake Tahoe
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North America
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Superb886 reviews4.9
Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing advent....
Private Tour
Best Private Luxury Daytime Boat Tour in New York City - 2 Hour
Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view of the Manhattan skyline, Freedom Tower, Brooklyn Bridge, Empire ... More
Private Tour
Likely to Sell Out Best Private Luxury Daytime Boat Tour in New York City - 2 Hour
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North America
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Superb88 reviews5
Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manh....
Private Tour
Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling
Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical waters alongside colorful sea life. The bilingual crew is happy to accommodate any special occasion or request. This unforgettable ex... More
Private Tour
Likely to Sell Out Cabo San Lucas Private 38 ft Sailing Tour with Snorkeling
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North America
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Superb185 reviews5
Sail from Cabo San Lucas on a beautiful private 38 feet sailing boat and snorkel in tropical water....
Private Tour
Boston Harbor Sunset Sail Tour
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adir... More
Private Tour
Likely to Sell Out Boston Harbor Sunset Sail Tour
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North America
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Superb132 reviews4.8
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....
Private Tour
Skagway Trail and Sail
This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike Electric Bicycles where you will join us for a self-guided ride to some of Skagway's best sites! You will visit a waterfall, scenic... More
Private Tour
Likely to Sell Out Skagway Trail and Sail
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North America
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Superb5 reviews4.8
This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike E....
Private Tour
Whale Watching Sail in Honolulu with Open Bar
Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while searching for dolphins and sea turtles in their natural habitat.... More
Private Tour
Likely to Sell Out Whale Watching Sail in Honolulu with Open Bar
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North America
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Superb11 reviews5
Observe the majestic humpback whales during their migration from December to March on this 1.5-hour ....
Private Tour