Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 701 Sailing Trips activities in North America. Sort by Popularity. - Page 5Sunset or Afternoon Sail On A Vintage Yacht Beer & Wine Included
Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica of a 1904 gaff rigged friendship sloop. She is an elegant sight under sail, featuring; highly finished woodwork, bronze fixtures, a... More

Sunset or Afternoon Sail On A Vintage Yacht Beer & Wine Included
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North America
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Superb307 reviews4.9
Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica o....
Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"
Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ... More

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"
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North America
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Superb11 reviews4.7
Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This ....
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

Private Fishing Trip "All Inclusive" in Cabo San Lucas, Mexico
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North America
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Superb320 reviews4.8
Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....
Private Tour
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
Private Tour

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail
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North America
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Exellent357 reviews4.4
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....
Private Tour
2-Hour Private Sailing Experience in San Diego Bay
Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing to obtain in today's world. With all the stress life brings we are happy to provide a peacefu... More
Free Cancellation
Private Tour
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2-Hour Private Sailing Experience in San Diego Bay
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North America
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Superb157 reviews5
Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....
Free Cancellation
Private Tour
(Saving 6% )
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
Private Tour

Half-Day Luxury Sailing Experience in Tulum with Open Bar
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North America
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Exellent242 reviews4.2
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
Private Tour
Windjammer Classic Sunset Sail from Camden, Maine
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More
Private Tour

Windjammer Classic Sunset Sail from Camden, Maine
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North America
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Superb371 reviews4.9
Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....
Private Tour
Schooner Fame Sailing Tour
FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per TripAdvisor. Don't miss the very best of what Salem has to offer! There's more to our town than witches! FAME is a full-scale replica... More
Private Tour

Schooner Fame Sailing Tour
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North America
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Superb543 reviews4.9
FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per Trip....
Private Tour
Key West Afternoon Reef Snorkeling with Open Bar
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More
Private Tour

Key West Afternoon Reef Snorkeling with Open Bar
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North America
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Exellent377 reviews4.5
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....
Private Tour
Dolphin Adventure Sail in Cocoa Beach
Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter pla... More
Private Tour

Dolphin Adventure Sail in Cocoa Beach
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North America
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Superb151 reviews4.9
Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....
Private Tour
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More
Private Tour

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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North America
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Superb32 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Private Tour
Key West Reef Snorkel & Sail 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
Private Tour

Key West Reef Snorkel & Sail Adventure
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North America
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Superb521 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Private Tour
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More
Private Tour

Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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North America
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Superb129 reviews4.9
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
Private Tour
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
Private Tour

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
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North America
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Superb135 reviews4.7
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....
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

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
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North America
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Superb650 reviews5
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....
Private Tour

Day Sail from Traverse City with Food, Wine, & Cocktails
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North America
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Superb140 reviews4.9
For a full description please visit our website at https://www.winddancertc.com/ where you can learn....
Private Tour
El Cielo Snorkel by Private Boat
- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and coral formations - Stop over at a secluded pristine white sandy beach away from the crowds - Taste a delicious fish ceviche and co... More
Private Tour

El Cielo Snorkel by Private Boat
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North America
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Superb317 reviews4.8
- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and co....
Private Tour
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More
Private Tour

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
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North America
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Superb87 reviews4.6
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....
Private Tour
Buccaneer Pirate Cruise in Destin
Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family! Enjoy a fun cruise with interactive pirate-themed activities, entertainment, and treasure hunts. Take in the beauty of the Emeral... More
Private Tour

Buccaneer Pirate Cruise in Destin
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North America
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Superb78 reviews4.9
Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....
Private Tour
Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting
DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews on Google. What you will get: Nature Immersion: Encounter dolphins, turtles, manatees, and more as you explore Miami's waters Cel... More
Private Tour

Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting
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North America
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Superb56 reviews4.7
DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews ....
Private Tour