Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 719 Sailing Trips activities in North America. Sort by Popularity. - Page 6Sunset Sailing Cruise in Monterey Bay
Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is the most popular (and most romantic!) way to experience Monterey Bay. Departing daily, 90 minutes before sunset, this dreamy 1.5-... More

Sunset Sailing Cruise in Monterey Bay
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North America
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Superb34 reviews4.8
Looking to impress your date or just treat yourself to something unforgettable? Our Sunset Cruise is....
Daytime Sailing Along San Diego's Skyline
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on thisfamily-friendly sailing experience. We'll set sail from Safeharbor Sunroad Marina on Harbor Island on San Diego Bay, we often s... More

Daytime Sailing Along San Diego's Skyline
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North America
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Superb145 reviews4.9
Set sail with your Captain aboard our sail yacht and see some of San Diego's finest highlights on th....
Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max)
Sail in style aboard Cozumel’s largest and most spacious catamaran—a 47ft Nautitech—on an unforgettable journey to the famous El Cielo sandbar! Just 5–10 minutes by taxi from any cruise terminal or downtown, enjoy award-wi... More
Private Tour

Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max)
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North America
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Superb15 reviews4.7
Sail in style aboard Cozumel’s largest and most spacious catamaran—a 47ft Nautitech—on an unfo....
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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Superb154 reviews4.8
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
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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Exellent363 reviews4.4
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....
Private Tour

Kona Tradewind Catamaran Day Sail
Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunning Kona coastline. This relaxing daytime cruise is perfect for spotting Hawaii’s incredible marine wildlife—keep your eyes peel... More
Free Cancellation
Private Tour
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Kona Tradewind Catamaran Day Sail
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North America
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Superb40 reviews4.8
Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunnin....
Free Cancellation
Private Tour
(Saving 16% )

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
(Saving 10% )

2-Hour Private Sailing Experience in San Diego Bay
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North America
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Superb167 reviews5
Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....
Free Cancellation
Private Tour
(Saving 10% )
New York Harbor Wine and Jazz Sail aboard Clipper City
Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views of New York City on this entertaining evening jazz sail. From the decks of the boat, you will enjoy breathtaking views of the Manha... More
Private Tour

New York Harbor Wine and Jazz Sail aboard Clipper City
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North America
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Exellent21 reviews4.4
Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views o....
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

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....
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North America
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Superb158 reviews4.7
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....
Private Tour
Deluxe Sail & Snorkel to the Captain Cook Monument
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters... More
Private Tour

Deluxe Sail & Snorkel to the Captain Cook Monument
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North America
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Superb464 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....
Private Tour
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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Superb809 reviews4.9
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....
Private Tour
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 charterÂ... More
Private Tour

Private Sailing Charter on San Diego Bay
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North America
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Superb35 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
Luxury Sailing Tour of San Diego's Bay and Coastal Waterways
This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways. You'll be on a beautiful Catalina 34' Sailboat enjoying the fresh air and best that San Diego has to offer. On your adventure yo... More
Private Tour

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways
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North America
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Superb202 reviews4.9
This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....
Private Tour
Statue of Liberty Sunset Cruise and New York City Sky Line
New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View of the Manhattan skyline, One World Trade Center and the Empire State Building.Enjoy a panoramic view of lower Manhattan as you p... More
Private Tour

Statue of Liberty Sunset Cruise and New York City Sky Line
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North America
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Good41 reviews3.1
New York City Sightseeing Scenic cruise. Enjoy the Statue of Liberty and Ellis Island up close. View....
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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Superb125 reviews4.6
Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....
Private Tour
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More
Private Tour

Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling
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North America
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Superb432 reviews4.9
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....
Private Tour
Panama City Beach Dolphin Sightseeing Sail
This cruise along the Gulf Coastline and Bay area offers a great opportunity to photograph local wildlife and scenery. At our onboard bar we have snacks and beverages available for purchase. Enjoy a variety of cocktails, including... More
Private Tour

Panama City Beach Dolphin Sightseeing Sail
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North America
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Superb116 reviews4.8
This cruise along the Gulf Coastline and Bay area offers a great opportunity to photograph local wil....
Private Tour
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
Private Tour

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"
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North America
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Superb20 reviews4.8
Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This ....
Private Tour
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), 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 pal... More
Private Tour

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)
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North America
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Superb83 reviews5
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Private Tour
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
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

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
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North America
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Superb82 reviews4.8
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....
Private Tour