Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 727 Sailing Trips activities in North America. Sort by Popularity. - Page 15Sunset sail Aboard Manakai Catamaran
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a smaller guest capacity and open-deck layout, it offers an intimate, lai... More
Sunset sail Aboard Manakai Catamaran
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North America
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Superb13 reviews5
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....
kayaking in Huatulco
The geographical position favors us to observe whales, dolphins, turtles and much more while sailing in the kayak in calm waters, we have contact with the most 95% of the time on the tour, so it is highly recommended for biologist... More
Private Tour
kayaking in Huatulco
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North America
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Superb1 review5
The geographical position favors us to observe whales, dolphins, turtles and much more while sailing....
Private Tour
Los Cabos Seasonal Whale Watch and Snorkel Tour
Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful Marina in Cabo San Lucas the boat as sails towards the Santa Maria or Chileno Bay, will ride along the Sea of Cortes, and you will ... More
Private Tour
Los Cabos Seasonal Whale Watch and Snorkel Tour
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North America
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Superb19 reviews4.7
Available December 15th to April 15th. Enjoy an incredible adventure, departing from the beautiful M....
Private Tour
Shallow Water Snorkeling and Dolphin Watching in Key West
All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo - making vacation memories since 1991. Enjoy a premium shallow snorkeling and dolphin-watc... More
Private Tour
Likely to Sell Out Shallow Water Snorkeling and Dolphin Watching in Key West
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North America
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Superb464 reviews4.6
All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropica....
Private Tour
2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks
With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on the sea. 2.5 hour tour length is perfect for seeing all the beautiful sights. Catamarans reall... More
Private Tour
Likely to Sell Out 2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks
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North America
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Superb81 reviews5
With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepare....
Private Tour
Key West Day Sail on Schooner America 2.0 with 2 Drinks
Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean... More
Private Tour
Likely to Sell Out Key West Day Sail on Schooner America 2.0 with 2 Drinks
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North America
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Superb192 reviews4.9
Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a ....
Private Tour
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms
Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips be... More
Private Tour
Likely to Sell Out Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms
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North America
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Superb45 reviews4.9
Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....
Private Tour
NYC Statue of Liberty Tall Ship Sail aboard Clipper City
Step aboard the majestic Clipper City and feel the city fade into the background as the wind fills the sails. Glide through New York Harbor in style, with the Brooklyn Bridge, Statue of Liberty, Ellis Island, and the glittering Ma... More
Private Tour
Likely to Sell Out NYC Statue of Liberty Tall Ship Sail aboard Clipper City
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North America
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Exellent264 reviews4.3
Step aboard the majestic Clipper City and feel the city fade into the background as the wind fills t....
Private Tour
Vancouver Sailing Experience on a 50 foot Sailboat
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More
Private Tour
Likely to Sell Out Vancouver Sailing Experience on a 50 foot Sailboat
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North America
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Superb100 reviews5
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....
Private Tour
Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline
Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Miami Beach experience. Connect with nature, discover new landscapes, & create lasting memories as you explore the stunning coastline... More
Private Tour
Likely to Sell Out Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline
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North America
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Superb23 reviews4.8
Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Mia....
Private Tour
Suncoast Sailing's Day Sailing Experience!
Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. Feel the wind as it glides us through the picturesque waters of Treasure Island and Gulf of Mexico. Come face to face with nature a... More
Private Tour
Likely to Sell Out Suncoast Sailing's Day Sailing Experience!
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North America
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Superb104 reviews4.9
Join us aboard the iconic schooner, Suncoast Horizon and step aboard our 2 hour sailing excursion. F....
Private Tour
Kona Tradewind Catamaran Day Sail
Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparklin... More
Private Tour
Likely to Sell Out Kona Tradewind Catamaran Day Sail
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North America
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Superb42 reviews4.8
Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....
Private Tour
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pals on ou... More
Private Tour
Likely to Sell Out Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
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North America
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Superb26 reviews5
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....
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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Superb6 reviews5
Observe the majestic humpback whales during their migration from December to March on this 1.5-hour ....
Private Tour
Sunrise by Paddle or Kayak with Floating Picnic
Dare to live a new experience! During this activity you will connect with your ecological SELF as you paddle towards sunrise. Enjoy a delicious picnic in a natural environment while you immerse yourself in warm and crystal clear w... More
Private Tour
Likely to Sell Out Sunrise by Paddle or Kayak with Floating Picnic
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North America
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Superb339 reviews5
Dare to live a new experience! During this activity you will connect with your ecological SELF as yo....
Private Tour
Sunset Sail Aboard the 47 ft Daydreams Sailboat
Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way. Wit... More
Private Tour
Likely to Sell Out Sunset Sail Aboard the 47 ft Daydreams Sailboat
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North America
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Superb32 reviews4.9
Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Gran....
Private Tour
Cancun to Isla Mujeres Full Day Tour with Snorkeling
Live a fun and relaxed day aboard a catamaran with open bar on board meeting the pearl of the Caribbean – Isla Mujeres, with its paradise beaches. We start the catamaran tour with national open bar included on board throughout ... More
Private Tour
Likely to Sell Out Cancun to Isla Mujeres Full Day Tour with Snorkeling
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North America
Live a fun and relaxed day aboard a catamaran with open bar on board meeting the pearl of the Carib....
Private Tour
Jungle Tour
This boat and snorkeling tour from Cancun gives you a 2-for-1 value—take a speedboat ride through Nichupte Lagoon and snorkel in the El Angel coral reef. Choose to take the driver’s seat or ride shotgun in a 2-seat speedboat a... More
Private Tour
Likely to Sell Out Jungle Tour
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North America
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Superb1 review5
This boat and snorkeling tour from Cancun gives you a 2-for-1 value—take a speedboat ride through ....
Private Tour
Waikiki 3pm Tradewind Sail - Open Bar Included
Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoon in the sun. We'll be keeping a sharp eye out for dolphin... More
Private Tour
Likely to Sell Out Waikiki 3pm Tradewind Sail - Open Bar Included
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North America
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Superb245 reviews4.8
Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise ....
Private Tour
Snorkeling Adventure in Isla Mujeres
Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum is a unique activity in the world since there is no such thing anywhere. This activity is cataloged as mandatory for all traveler... More
Private Tour
Likely to Sell Out Snorkeling Adventure in Isla Mujeres
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North America
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Very Good12 reviews3.8
Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum....
Private Tour