Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 734 Sailing Trips activities in North America. Sort by Popularity. - Page 5Golden Hour Whale Watch from Lahaina
Set sail aboard ‘Alihilani, our 64-foot Gold Coast sailing catamaran, for a stunning Late Afternoon Whale Watch from 3:30 to 5:30 PM, departing daily from Lahaina Harbor. Enjoy Maui’s golden light as humpback whales breach, gl... More
Golden Hour Whale Watch from Lahaina
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North America
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Superb42 reviews5
Set sail aboard ‘Alihilani, our 64-foot Gold Coast sailing catamaran, for a stunning Late Afternoo....
1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along Florida’s Intracoastal Waterway that’s fun for the whole family! T... More
1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
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North America
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Superb1,489 reviews4.9
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....
Private Sailing Charter on San Diego Bay
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing yacht with a knowledgeable and friendly Captain? This private charter... More
Private Tour
Private Sailing Charter on San Diego Bay
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North America
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Superb41 reviews4.9
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....
Private Tour
Cancun Pirate Ship Adventure : Dinner & Show at Sea 2 for 1 Deal
Set sail EN an unforgettable adventure at DEcer with the Pirate Ship EN Cancun show, aboard a majestic Spanish galleon DE. Experience an exciting pirate experience filled DE games, contests and the fascinating stories of the Capta... More
Private Tour
Cancun Pirate Ship Adventure : Dinner & Show at Sea 2 for 1 Deal
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North America
Set sail EN an unforgettable adventure at DEcer with the Pirate Ship EN Cancun show, aboard a majest....
Private Tour
Key West Dolphin and Snorkel Experience
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.... More
Free Cancellation
Private Tour
(Saving 10% )
Key West Dolphin and Snorkel Experience
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North America
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Exellent338 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
Free Cancellation
Private Tour
(Saving 10% )
Sunset and Manta Ray Snorkel Adventure
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays! Upon arriving, receive an in... More
Private Tour
Sunset and Manta Ray Snorkel Adventure
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North America
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Superb844 reviews4.9
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....
Private Tour
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More
Private Tour
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
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North America
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Superb282 reviews4.8
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....
Private Tour
Suncoast Sailing's Sunset Sailing Experience!
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Treasure Island, Florida! You’ll set sail about an hour before sunset to give you plenty of time to catch the full range of hues p... More
Private Tour
Suncoast Sailing's Sunset Sailing Experience!
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North America
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Superb258 reviews4.9
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....
Private Tour
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More
Private Tour
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun
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North America
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Superb157 reviews4.8
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
Private Tour
Snorkel with Manta Rays Guaranteed
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More
Private Tour
Likely to Sell Out Snorkel with Manta Rays Guaranteed
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North America
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Superb739 reviews4.8
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....
Private Tour
Monterey Bay Whale Watching
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watching tours depart from Moss Landing, right at the mouth of the Monterey Bay Canyon, one of the largest underwater canyons in the wor... More
Private Tour
Likely to Sell Out Monterey Bay Whale Watching
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North America
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Superb321 reviews4.6
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....
Private Tour
Waikiki small group turtle snorkeling & sailing
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More
Private Tour
Likely to Sell Out Waikiki small group turtle snorkeling & sailing
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North America
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Superb89 reviews5
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....
Private Tour
Key West Champagne Sunset Catamaran Cruise
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy included wine, sparkling wine, beer, sangria or margaritas on board the boat. . As you sail thr... More
Private Tour
Likely to Sell Out Key West Champagne Sunset Catamaran Cruise
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North America
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Superb587 reviews4.7
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of t....
Private Tour
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
Private Tour
Likely to Sell Out Evening Colors Sunset Sail Tour in Seattle
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North America
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Superb593 reviews4.8
Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....
Private Tour
Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More
Private Tour
Likely to Sell Out Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran
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North America
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Superb87 reviews4.7
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....
Private Tour
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands... More
Private Tour
Likely to Sell Out Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
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North America
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Superb95 reviews4.9
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....
Private Tour
Mexico City: Xochimilco at sunrise + Breakfast and transportation
Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural beauty, the tranquility of the sunrise and respect for the environment. This is not the traditional Xochimilco of the trajineras;... More
Private Tour
Likely to Sell Out Mexico City: Xochimilco at sunrise + Breakfast and transportation
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North America
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Superb103 reviews5
Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural....
Private Tour
Sunset Sail in Miami: Complimentary Champagne Toast
Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for sun dresses, sandals and chilled wine. Take advantage of one of Florida's finest highlights upon our comfortable 80 ft catamaran a... More
Private Tour
Likely to Sell Out Sunset Sail in Miami: Complimentary Champagne Toast
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North America
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Superb233 reviews4.8
Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for ....
Private Tour
Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your loved ones to experience a beautiful Snorkeling, Sailing Cruise, and Whale Watching (Dec-Apr) on our Small Charming Hawaiian Catamara... More
Private Tour
Likely to Sell Out Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....
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North America
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Superb160 reviews4.7
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....
Private Tour
Premium Isla Mujeres Tour by Private Catamaran
We specialize in making this all-day trip unique, a unique and beautiful experience for all our guests. This trip can always be customized as desired, as we offer 2 options to our customers. Our trained team is always there to pro... More
Private Tour
Likely to Sell Out Premium Isla Mujeres Tour by Private Catamaran
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North America
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Superb336 reviews4.9
We specialize in making this all-day trip unique, a unique and beautiful experience for all our gues....
Private Tour