Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 676 Sailing Trips activities in North America. Sort by Popularity.Isla Mujeres Luxury Catamaran Sailing plus Lunch and Open Bar
Join us for the Luxury Sailing Adventure to Isla Mujeres onboard a state of the art sailing catamaran. You'll explore some of the most beautiful locations along Cancun’s stunning Caribbean coastline where you will go snorkeling... More

Isla Mujeres Luxury Catamaran Sailing plus Lunch and Open Bar
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North America
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Superb3,157 reviews4.7
Join us for the Luxury Sailing Adventure to Isla Mujeres onboard a state of the art sailing catamar....
2-Hour Whale Watching from Oahu
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More

2-Hour Whale Watching from Oahu
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North America
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Superb853 reviews4.6
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....
Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and fea... More

Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres
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North America
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Superb3,084 reviews4.7
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....
Los Cabos Luxury Sailing, Snorkel and Lunch Cruise
Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time to hang out in the pristine water and take it easy aboard the sailboat – you can snorkel with tropical fish, stand atop a paddleb... More

Los Cabos Luxury Sailing, Snorkel and Lunch Cruise
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North America
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Superb2,691 reviews4.8
Enjoy a relaxing half-day cruise aboard a luxury sailboat off the Cabo coast. Indulge in free time t....
Deluxe Na Pali Sunset Tour on the Lucky Lady
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look for dolphins, whales, and other marine critters as you sip a drink, snap som... More

Deluxe Na Pali Sunset Tour on the Lucky Lady
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North America
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Superb1,250 reviews4.7
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....
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

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....
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North America
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Superb3,289 reviews4.8
The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great w....
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More

Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast
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North America
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Superb1,871 reviews4.9
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....
Waikiki Catamaran Adventure: Snorkel with Sea Turtles
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More

Waikiki Catamaran Adventure: Snorkel with Sea Turtles
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North America
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Superb2,041 reviews4.7
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....
Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran
This is the best way to start your day on Oahu! Come snorkel with us at Turtle Canyon, a green sea turtle cleaning station. Our crew shows you not only turtles but also hidden creatures such as he’e (octopus) and ka hoku kai (st... More

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran
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North America
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Superb1,408 reviews4.8
This is the best way to start your day on Oahu! Come snorkel with us at Turtle Canyon, a green sea t....
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand K... More

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
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North America
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Superb655 reviews4.9
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....
Leila Na Pali Sunset Dinner Sail
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More

Leila Na Pali Sunset Dinner Sail
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North America
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Superb453 reviews4.7
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....
Pirate Ship Sunset Dinner and Show in Los Cabos
Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic sunset cruise with a show that is the joy for children and grown-ups alike. Our pirates, dance, chant, climb the ropes, while you... More

Pirate Ship Sunset Dinner and Show in Los Cabos
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North America
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Exellent567 reviews4.3
Come back in time, to the days when Cabo was home to pirates, onboard our pirate ships. A fantastic ....
Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
TRAVELER’S FAVORITE SNORKELING TRIP! Set off for a great Adventure to the Caribbean and admire the Spectacular marine life on this awarded Cozumel Snorkeling trip. Enjoy Cozumel's top attractions and most visited reefs in the ... More
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Cozumel Snorkeling Tour: Palancar, Columbia and El Cielo Reefs
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North America
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Exellent1,285 reviews4.3
TRAVELER’S FAVORITE SNORKELING TRIP! Set off for a great Adventure to the Caribbean and admire t....
Free Cancellation
(Saving 5% )
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

Sunset Catamaran Cruise in Ft. Lauderdale
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North America
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Superb624 reviews4.8
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....
Live Music Sunset Sail with Drinks Included
Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sail! Indulge in complimentary beer, wine, soda, water, margaritas, champagne, and a snack, while enjoying live performances by some ... More

Live Music Sunset Sail with Drinks Included
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North America
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Superb99 reviews4.8
Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all inclusive sunset sai....
Sunset & Dolphin Catamaran Cruise with Island Time
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More

Sunset & Dolphin Catamaran Cruise with Island Time
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North America
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Superb1,476 reviews4.9
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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North America
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Superb774 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
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

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
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North America
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Superb606 reviews4.6
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....
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

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....
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North America
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Superb132 reviews4.6
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....
Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB
AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE COME SEE OUR COMPLETELY REIMAGINED VESSEL! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off o... More

Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB
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North America
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Superb601 reviews4.9
AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE C....