Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 727 Sailing Trips activities in North America. Sort by Popularity. - Page 4Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran
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
Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran
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North America
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Superb83 reviews4.7
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....
Sunset Sail Along the San Diego Skyline
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on San Diego that you can only get from the water. Our San Diego Bay Sunset Sailing Cruises provide an up-close and personal view o... More
Sunset Sail Along the San Diego Skyline
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North America
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Superb600 reviews4.9
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time
The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great way to have fun in the sun and enjoy the best of what Panama City Beach has to offer! Cruise over to Shell Island where you and the... More
Likely to Sell Out Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....
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North America
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Superb4,361 reviews4.9
The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great w....
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
Likely to Sell Out Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling
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North America
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Superb438 reviews4.9
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....
2-Hour Sunset Sail on the San Francisco Bay
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour sunset sail is just the ticket. Step aboard the gorgeous traditional vessel to take in the sights at the most bewitching time of d... More
Likely to Sell Out 2-Hour Sunset Sail on the San Francisco Bay
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North America
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Superb391 reviews4.7
Whether you want to kick off a fabulous date night or wrap up an enjoyable afternoon, this two-hour ....
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor
Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall Ship for a unique sailing experience. There is no better way to witness all o... More
Likely to Sell Out Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbo....
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North America
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Exellent620 reviews4.5
Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience histor....
Mexico City: Xochimilco at sunrise + Breakfast and transportation
Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural beauty, the tranquility of the sunrise and respect for the environment. This is not the traditional Xochimilco of the trajineras;... More
Likely to Sell Out Mexico City: Xochimilco at sunrise + Breakfast and transportation
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North America
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Superb97 reviews5
Discover a totally different face of Xochimilco, away from the tourist bustle and focused on natural....
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
Likely to Sell Out Sunset and Manta Ray Snorkel Adventure
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North America
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Superb838 reviews4.9
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....
1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along Florida’s Intracoastal Waterway that’s fun for the whole family! T... More
Likely to Sell Out 1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
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North America
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Superb1,478 reviews4.9
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....
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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Superb397 reviews4.7
Embark on the most exciting fishing adventure in the crystal-clear waters of Cabo San Lucas. Our all....
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
Likely to Sell Out Sunset Sail in Miami: Complimentary Champagne Toast
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North America
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Superb230 reviews4.8
Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for ....
Private Tour
Waikiki small group turtle snorkeling & sailing
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More
Private Tour
Likely to Sell Out Waikiki small group turtle snorkeling & sailing
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North America
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Superb86 reviews5
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....
Private Tour
Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar
Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the best reefs and see beautiful tropical fish. Enjoy a delicious buffet lunch on our private beach club, and then tour Isla Mujeres to s... More
Private Tour
Likely to Sell Out Cancun Adults Only Party Cruise to Isla Mujeres with Open Bar
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North America
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Very Good205 reviews3.7
Take a Party Cruise Adult Only from Cancun to Isla Mujeres. Make a stop to snorkel at one of the bes....
Private Tour
Classic Key West Schooner Sunset Sail with Full Open Bar
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More
Private Tour
Likely to Sell Out Classic Key West Schooner Sunset Sail with Full Open Bar
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North America
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Superb207 reviews4.9
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
Private Tour
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
Private Tour
Likely to Sell Out Panama City Beach Sunset Catamaran Sail on The Privateer
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North America
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Superb709 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
Private 40' Bali Catamaran – Drinks & Food Included
It is an incredible and unique experiences because for 4 hours you will be the owner of this incredible sailing catamaran, with a host and a chef at your disposal, the captain will take you to sail in the most beautiful waters of ... More
Private Tour
Likely to Sell Out Private 40' Bali Catamaran – Drinks & Food Included
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North America
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Superb348 reviews5
It is an incredible and unique experiences because for 4 hours you will be the owner of this incredi....
Private Tour
Golden Hour Whale Watch from Lahaina
Set sail aboard ‘Alihilani, our 64-foot Gold Coast sailing catamaran, for a stunning Late Afternoon Whale Watch from 3:30 to 5:30 PM, departing daily from Lahaina Harbor. Enjoy Maui’s golden light as humpback whales breach, gl... More
Private Tour
Likely to Sell Out Golden Hour Whale Watch from Lahaina
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North America
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Superb9 reviews5
Set sail aboard ‘Alihilani, our 64-foot Gold Coast sailing catamaran, for a stunning Late Afternoo....
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
Likely to Sell Out 2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)
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North America
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Superb97 reviews5
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Private Tour
Sunset Catamaran Cruise in Ft. Lauderdale
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More
Private Tour
Likely to Sell Out Sunset Catamaran Cruise in Ft. Lauderdale
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North America
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Superb692 reviews4.8
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....
Private Tour
Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise
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
Likely to Sell Out Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise
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North America
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Superb79 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Private Tour