Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 701 Sailing Trips activities in North America. Sort by Popularity. - Page 4Sunset Sip and Sail Key West with Open Bar and Live Music
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More

Sunset Sip and Sail Key West with Open Bar and Live Music
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North America
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Superb273 reviews4.6
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. ....
Sunset Sail in Key West with Beverages Included
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More

Sunset Sail in Key West with Beverages Included
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North America
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Superb850 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
Key West Snorkeling with Breakfast and Unlimited Mimosas
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More

Key West Snorkeling with Breakfast and Unlimited Mimosas
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North America
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Exellent540 reviews4.5
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....
Kona Catamaran Sunset Sail
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More

Kona Catamaran Sunset Sail
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North America
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Superb162 reviews4.8
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....
Newport Afternoon Sightseeing Sail on Classic Sailboat
Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail, including Newport's historic lighthouses and landmarks, bridges, mansions a... More

Newport Afternoon Sightseeing Sail on Classic Sailboat
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North America
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Superb97 reviews4.8
Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narraga....
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

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun
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North America
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Superb150 reviews4.8
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
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North America
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Superb45 reviews4.6
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
Private Catamaran Escape for 2–6 Guests – Celebrate Your Way”
Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re celebrating a bachelorette, a birthday, or simply enjoying time with your favorite people, this catamaran getaway for up to six gues... More
Private Tour

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way....
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North America
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Superb308 reviews4.9
Set sail on a one-of-a-kind ocean escape designed for small, meaningful moments. Whether you’re ce....
Private Tour
Sunset Sailing Cruise on a Tall Ship in Boston Harbor
If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic Boston tall ship! We depart Fan Pier Marina and raise the sails, then it’s time to just chill out and relax. Get a... More
Private Tour

Sunset Sailing Cruise on a Tall Ship in Boston Harbor
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North America
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Superb393 reviews4.6
If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise....
Private Tour
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy ... More
Private Tour

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
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North America
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Superb1,256 reviews4.9
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....
Private Tour
Panama City Beach Sunset Sail on The Footloose Catamaran
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More
Private Tour

Panama City Beach Sunset Sail on The Footloose Catamaran
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North America
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Superb413 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
Private Tour
New York City Sailboat Day Cruise to the Statue of Liberty
Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides along the Hudson Rive... More
Private Tour

New York City Sailboat Day Cruise to the Statue of Liberty
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North America
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Superb128 reviews4.9
Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by t....
Private Tour
Sailing Experience on a 50’ 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

Sailing Experience on a 50’ sailboat
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North America
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Superb81 reviews5
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....
Private Tour
New York Sunset Schooner Cruise on the Hudson River
Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known as Schooner Adirondack - inspired by the pilot schooners of... More
Private Tour

New York Sunset Schooner Cruise on the Hudson River
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North America
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Superb205 reviews4.9
Experience a New York City sunset from the water on this evening sightseeing sail past many famous w....
Private Tour
Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos. Learn how to walk and talk like a pirate then climb aboard the Black Dagger and set sail in search of treasure! But wait it's not... More
Private Tour

Hilton Head Pirate Ship Adventure Sail aboard the Black Dagger
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North America
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Superb658 reviews4.9
The fun starts at the dock as we transform your little one with pirate gear, face paint and tattoos.....
Private Tour

Key West Dolphin and Snorkel Experience
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North America
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Exellent293 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
Private Tour
2.5 Hours of Fun: Catamaran Sunset Sail
Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and lounging around watching sea life, and water rush by. The swift and stable ocean design ensures a comfortable, and exhilarating ride wit... More
Private Tour

2.5 Hours of Fun: Catamaran Sunset Sail
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North America
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Superb185 reviews4.9
Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and loungi....
Private Tour
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More
Private Tour

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
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North America
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Superb659 reviews4.6
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....
Private Tour
Na Pali Coast Kauai Snorkel and Sail
Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and comfortable 50’ Kauai-built sailing catamaran, Leila. Let’s explore the cliffs, valleys, sea caves and wildlife of the Napali... More
Private Tour

Na Pali Coast Kauai Snorkel and Sail
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North America
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Superb519 reviews4.8
Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and....
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

Monterey Bay Whale Watching
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North America
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Superb289 reviews4.7
Sea Goddess Whale Watching promises a once-in-a-lifetime whale watching experience. Our whale watchi....
Private Tour