Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 4Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More
Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed
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North America
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Superb2,135 reviews4.7
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....
Half-Day Luxury Sailing Experience in Tulum with Open Bar
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More
Half-Day Luxury Sailing Experience in Tulum with Open Bar
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North America
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Exellent263 reviews4.2
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
Halifax Sunset Cruise Ft. a Live Musician
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on the Halifax Sunset Cruise aboard our signature ship, the Tall Ship Silva. Purchase wine, beer, cocktails, and other beverages from... More
Likely to Sell Out Halifax Sunset Cruise Ft. a Live Musician
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North America
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Superb99 reviews4.6
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on ....
4-Hour Private Fishing Charter in the Riviera Maya
Unlike many destinations, your fishing time starts within minutes of departure—no long boat rides—maximizing your time with lines in the water. This is a fully private experience, not a shared tour. The itinerary is flexible ... More
Private Tour
Likely to Sell Out 4-Hour Private Fishing Charter in the Riviera Maya
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North America
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Superb27 reviews5
Unlike many destinations, your fishing time starts within minutes of departure—no long boat ridesâ....
Private Tour
Nāpali Sunset Dinner Sail
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More
Private Tour
Likely to Sell Out Nāpali Sunset Dinner Sail
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North America
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Superb609 reviews4.7
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....
Private Tour
Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu
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
Private Tour
Likely to Sell Out Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu
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North America
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Superb1,336 reviews4.6
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....
Private Tour
San Francisco Bay Sailing Cruise
Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from the vantage point of the water. You’ll coast past the city skyline, the Gold... More
Private Tour
Likely to Sell Out San Francisco Bay Sailing Cruise
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North America
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Superb674 reviews4.9
Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sa....
Private Tour
Seattle Sailing Harbor Tour
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way to see the Seattle skyline, the beauty of the Puget Sound, even mountain views! We ... More
Private Tour
Likely to Sell Out Seattle Sailing Harbor Tour
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North America
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Superb593 reviews4.7
Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing t....
Private Tour
Puerto Vallarta Luxury Snorkel Sail with Open Bar and Lunch
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau sailboats, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra Madre mountains. This small-group experience offers a pe... More
Private Tour
Likely to Sell Out Puerto Vallarta Luxury Snorkel Sail with Open Bar and Lunch
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North America
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Superb322 reviews4.8
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau sailboats, taking in br....
Private Tour
Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico
Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all-inclusive fishing tour offers you a unique opportunity to immerse yourself in an authentic, action-packed fishing experience, wit... More
Private Tour
Likely to Sell Out Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico
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North America
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Superb547 reviews4.8
Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....
Private Tour
Kona Morning Snorkel to Captain Cook Monument
Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along the Kona coastline toward the Captain Cook Monument, where your adventure begins. Jump ... More
Private Tour
Likely to Sell Out Kona Morning Snorkel to Captain Cook Monument
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North America
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Superb485 reviews4.9
Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leavi....
Private Tour
Likely to Sell Out
Cabo San Lucas Small-Group Whale Watching Tour: Hear the Whales
Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade hydrophones. If whales are communicating, you may be lucky to get the rare opportunity to hear the whale songs live! Our RABEN (Me... More
Free Cancellation
Private Tour
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Likely to Sell Out Cabo San Lucas Small-Group Whale Watching Tour: Hear the Whales
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North America
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Superb17 reviews4.9
Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade h....
Free Cancellation
Private Tour
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Likely to Sell Out
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
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Private Tour
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Likely to Sell Out Key West Dolphin and Snorkel Experience
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North America
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Exellent374 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
Free Cancellation
Private Tour
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Likely to Sell Out
Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More
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Private Tour
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Likely to Sell Out Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
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North America
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Superb210 reviews4.7
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....
Free Cancellation
Private Tour
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Likely to Sell Out
Key West Sailing & Snorkeling: A Reef Adventure
Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More
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Private Tour
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Likely to Sell Out Key West Sailing & Snorkeling: A Reef Adventure
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North America
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Superb250 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Free Cancellation
Private Tour
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Likely to Sell Out
1.5-Hour San Francisco Bay Sailing Tour
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More
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Private Tour
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Likely to Sell Out 1.5-Hour San Francisco Bay Sailing Tour
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North America
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Superb406 reviews4.8
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....
Free Cancellation
Private Tour
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Likely to Sell Out
Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More
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Private Tour
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Likely to Sell Out Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail
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North America
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Exellent398 reviews4.4
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....
Free Cancellation
Private Tour
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Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay
Depart Keauhou Bay at 2:00 PM aboard the Hoku Nui — Sea Paradise’s 50-foot luxury sailing catamaran — and sail to the World Famous Captain Cook Monument at Kealakekua Bay, a Marine Life Conservation District on the Kona Coas... More
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Private Tour
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Likely to Sell Out Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay
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North America
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Superb743 reviews4.9
Depart Keauhou Bay at 2:00 PM aboard the Hoku Nui — Sea Paradise’s 50-foot luxury sailing catama....
Free Cancellation
Private Tour
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Likely to Sell Out
El Cielo Cozumel Snorkel trip by Catamaran
TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnificent reefs and great snorkeling and after, head back to a secluded Beach to relax and enjoy the beauty of Cozumel turquoise waters.... More
Free Cancellation
Private Tour
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Likely to Sell Out El Cielo Cozumel Snorkel trip by Catamaran
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North America
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Exellent286 reviews4.4
TRAVELER’S FAVORITE TRIP! Get in the mood for fun aboard your Catamaran in a fun sail to magnific....
Free Cancellation
Private Tour
(Saving 14% )
Likely to Sell Out
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
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Private Tour
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Likely to Sell Out Boston Harbor Sunset Sail Tour
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North America
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Superb199 reviews4.8
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....
Free Cancellation
Private Tour
(Saving inf% )