Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 668 Sailing Trips activities in North America. Sort by Popularity. - Page 3Southwest Florida Sunset Sail
SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The sunset hours are a magical time to be out on the water. With the winds calm, the sun turns g... More

Southwest Florida Sunset Sail
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North America
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Superb413 reviews4.9
SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....
Sunset Boat Cruise: Swim and Cruise Waikiki
There is no better place to swim than Waikiki and no better way to watch the sunset than from the Waikiki Coastline. Be amazed by the natural beauty as day turns to night and twilight blankets us with an array of amazing colors ... More

Sunset Boat Cruise: Swim and Cruise Waikiki
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North America
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Superb446 reviews4.7
There is no better place to swim than Waikiki and no better way to watch the sunset than from the Wa....
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

Evening Colors Sunset Sail Tour in Seattle
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North America
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Superb416 reviews4.8
Sailing aboard Seattle's premier tall ship is the best way to see our city from the water. Help hois....
Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas
Explore the sparkling turquoise waters of the Sea of Cortez on this sightseeing snorkel adventure of Los Cabos’ Land’s End Arch! First, you’ll enjoy a beautiful sightseeing stop at Pelican’s Rock where you’ll have a cha... More

Lands End Luxury Sail and Snorkel Cruise in Cabo San Lucas
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North America
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Superb755 reviews4.9
Explore the sparkling turquoise waters of the Sea of Cortez on this sightseeing snorkel adventure of....
Panama City Beach Sunset Catamaran Sail on The Privateer
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More

Panama City Beach Sunset Catamaran Sail on The Privateer
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North America
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Superb621 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
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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Superb300 reviews4.8
- Private and comfortable vessels - Snorkel at world famous reefs - Spectacular marine life and co....
Private Tour
Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar
Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail along the stunning coastline of the Riviera Maya aboard a luxurious catamaran, while Mother Nature prepares for her nightly performan... More
Private Tour

Riviera Maya Luxury Sunset Sailing plus Light Dinner and Open Bar
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North America
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Superb390 reviews4.6
Experience the sunset like never before on this fabulous Sunset Sailing excursion. You’ll sail alo....
Private Tour
2 Hour Sailing Cruise on Lake Tahoe
Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing adventure and include complementary local beer and wine, as well as non-alcoholic beverages on all of our daily cruises. Unlike other t... More
Private Tour

2 Hour Sailing Cruise on Lake Tahoe
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North America
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Superb681 reviews4.9
Sail Tahoe Blue is the premier sailing charter in South Lake Tahoe. We offer a unique sailing advent....
Private Tour
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
Private Tour

Boston Harbor Sunset Sail Tour
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North America
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Superb62 reviews4.7
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....
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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Superb54 reviews4.7
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....
Private Tour
Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar
Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This romantic sunset cruise on Cabo San Lucas Bay includes unlimited drinks from an open bar, accompanied by a delightful menu of small b... More
Private Tour

Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar
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North America
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Superb1,816 reviews4.8
Sail into the sunset along the Cabo coast and enjoy five-star service aboard a luxury yacht. This ro....
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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Exellent345 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
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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Superb267 reviews4.8
Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....
Private Tour
Day's End Cocktail Sunset Sail
Bring the whole family along for this upscale evening of outstanding food and beverages. We set the sails and chase the sun as it sets into the distant horizon of the azure water of the South Pacific. This casual dining experience... More
Private Tour

Day's End Cocktail Sunset Sail
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North America
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Superb21 reviews4.7
Bring the whole family along for this upscale evening of outstanding food and beverages. We set the ....
Private Tour
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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Exellent237 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
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More
Private Tour

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....
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North America
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Superb907 reviews4.7
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....
Private Tour
2-Hour Private Luxury Boat Tour in New York City
Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manhattan aboard a 30' luxurious powerboat. Get an unobstructed view of the Manhattan skyline, Freedom Tower, Brooklyn Bridge, Empire ... More
Private Tour

2-Hour Private Luxury Boat Tour in New York City
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North America
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Superb71 reviews5
Experience the breathtaking beauty of New York City on this private, 2-hour cruise around lower Manh....
Private Tour
Puerto Vallarta, Luxury Sunset Sailing
Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamarans. Relax and unwind as you enjoy delicious appetizers, a premium open bar, and top-tier service from our attentive crew. This i... More
Private Tour

Puerto Vallarta, Luxury Sunset Sailing
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North America
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Superb365 reviews4.7
Sail into one of Puerto Vallarta's stunning sunsets aboard our luxurious French sailboats or catamar....
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

Sunset Sail in Miami: Complimentary Champagne Toast
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North America
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Superb216 reviews4.8
Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for ....
Private Tour
Sunset Sail Experience at Kona from Honokohau
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
Private Tour

Sunset Sail Experience at Kona from Honokohau
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North America
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Superb145 reviews4.8
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....
Private Tour