Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 685 Sailing Trips activities in North America. Sort by Popularity. - Page 14Luxury 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

Luxury Sailing Tour of San Diego's Bay and Coastal Waterways
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North America
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Superb187 reviews4.9
This is an engaging and unique, small group tour, of San Diego's beautiful bay and coastal waterways....
Friday Night Firework Cruise in Waikiki
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More

Friday Night Firework Cruise in Waikiki
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North America
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Superb21 reviews4.8
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....
Puerto Vallarta Sunset Gourmet Experience
This experience blends fine dining, stunning scenery, and exceptional service in a way that few can match. The journey begins with a luxury catamaran cruise, offering panoramic views of Puerto Vallarta’s coastline at sunset. Unl... More

Puerto Vallarta Sunset Gourmet Experience
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North America
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Superb7 reviews4.7
This experience blends fine dining, stunning scenery, and exceptional service in a way that few can ....
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
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North America
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Exellent11 reviews4.5
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....
Private sailing tour of Bacalar Lagoon
Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper you. During the tour, you can enjoy a delicious fruit cocktail, water and beer. Our certified guides will make this tour an unfo... More
Private Tour

Private sailing tour of Bacalar Lagoon
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North America
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Superb294 reviews5
Enjoy a private Sailboat with the comforts and attention you deserve. Relax and let our team pamper ....
Private Tour
Deluxe Day Sail in San Diego
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our personalized day sailing experiences on the San Diego Bay offer a perfect blend of adventure and relaxation. With our passionate and kno... More
Free Cancellation
Private Tour
(Saving 7% )

Deluxe Day Sail in San Diego
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North America
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Superb47 reviews5
Set sail with San Diego Sailing Excursions and discover what sets us apart from the rest. Our person....
Free Cancellation
Private Tour
(Saving 7% )
Cozumel Private Snorkeling and Charter Experience
We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On this tour, you'll have your own completely private charter visiting the famous 'El Cielo' and other amazing destinations to give you... More
Private Tour

Cozumel Private Snorkeling and Charter Experience
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North America
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Superb25 reviews5
We're known for operating the best all-inclusive snorkel experiences on the island of Cozumel. On th....
Private Tour
Cabo Snorkeling and Sailboat Tour with Lunch and Open Bar
Embark on a 3-hour sailing & snorkeling expedition to Land’s End and Pelican’s Rock. Take your picture at The Arch, one of Cabo’s main landmarks, and get a glimpse of Lover’s Beach and the Sea Lion Colony. Known as the a... More
Private Tour

Cabo Snorkeling and Sailboat Tour with Lunch and Open Bar
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North America
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Superb3 reviews4.7
Embark on a 3-hour sailing & snorkeling expedition to Land’s End and Pelican’s Rock. Take your ....
Private Tour
Isla Mujeres Catamaran Sailing Experience with Lunch & Open Bar
Set off on a sun-and-fun-packed day trip to charming Isla Mujeres, a must-see attraction just off the Cancun coast. Cruise on a modern catamaran while sipping a drink or two from the open bar on your way to and from the scenic isl... More
Private Tour

Isla Mujeres Catamaran Sailing Experience with Lunch & Open Bar
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North America
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Very Good16 reviews3.8
Set off on a sun-and-fun-packed day trip to charming Isla Mujeres, a must-see attraction just off th....
Private Tour
Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More
Private Tour

Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan
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North America
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Superb24 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Private Tour
Deluxe Catamaran to Isla Mujeres, with Drinks, Snorkel & Buffet
Get ready to venture into a fantastic experience aboard our catamaran to Isla Mujeres. You will board the catamaran and we will begin our tour together with our guides and entertainers so that you have a pleasant time. You can as... More
Private Tour

Deluxe Catamaran to Isla Mujeres, with Drinks, Snorkel & Buffet
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North America
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Very Good17 reviews3.8
Get ready to venture into a fantastic experience aboard our catamaran to Isla Mujeres. You will boa....
Private Tour
Sailing Adventure on Okanagan Lake from Penticton & Naramata BC
Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht into the sunny waters of Okanagan Lake. We provide hands on instruction and lots of opportunities to learn or just relax. And it is ... More
Private Tour

Sailing Adventure on Okanagan Lake from Penticton & Naramata BC
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North America
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Superb43 reviews5
Sailing is a life changing experience! In four hours, you will help sail a large sailing yacht int....
Private Tour
Private 2-Hour Morning Sail
Have you ever wanted to go sailing in the San Francisco Bay area but didn’t know anyone with a boat? Come sail with me, Captain John. Let me share my passion for sailing with you. I’m a U.S. certified sailing instructor and li... More
Private Tour

Private 2-Hour Morning Sail
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North America
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Superb5 reviews5
Have you ever wanted to go sailing in the San Francisco Bay area but didn’t know anyone with a boa....
Private Tour
Newport Sunset Sail on Schooner Adirondack
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailbo... More
Private Tour

Newport Sunset Sail on Schooner Adirondack
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North America
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Superb36 reviews4.9
Join us aboard a classic sailboat for a 1.5-hour sunset sail in Newport! Sunset sailing is one of th....
Private Tour
Chacahua Afternoon Journey
As a team we try to create journeys that are worth investing your time and confidence. We try to do our best to get out of the same schedules that our fellow colleagues offer this tour is whole afternoon experience that show us al... More
Private Tour

Chacahua Afternoon Journey
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North America
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Superb13 reviews4.9
As a team we try to create journeys that are worth investing your time and confidence. We try to do ....
Private Tour

Laguna Grill - Private Boat with on-board BBQ and Drinks Included
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North America
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Superb122 reviews5
One of a kind in Bacalar! Cruise, swim, eat and drink in Bacalars most complete activity. Enjoy natu....
Private Tour
Private Kelowna Sailing Cruise on Okanagan Lake
Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are welcome to sit back and relax, enjoy the sights, or take a turn at the helm, with instruction from your skipper! I will never forg... More
Private Tour

Private Kelowna Sailing Cruise on Okanagan Lake
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North America
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Superb32 reviews5
Sailing is a quiet, peaceful experience, as the boat is powered by nothing but the wind. You are w....
Private Tour
Luxury Catamaran tour to isla mujeres with transportation from Tulum
Excellent service on board Professional crew members Safety measures in all our activities Sanitary prevention protocols for all our guests and staff Once in a lifetime experience Delicious buffet lunch and drinks Beach club (beac... More
Private Tour

Luxury Catamaran tour to isla mujeres with transportation from Tu....
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North America
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Good62 reviews3.5
Excellent service on board Professional crew members Safety measures in all our activities Sanitary ....
Private Tour
Schooner Fame Sailing Tour
FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per TripAdvisor. Don't miss the very best of what Salem has to offer! There's more to our town than witches! FAME is a full-scale replica... More
Private Tour

Schooner Fame Sailing Tour
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North America
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Superb524 reviews4.9
FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per Trip....
Private Tour
Private Day Sailing Experience in San Diego up to 12 guests
This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San Diego landmarks along downtown where we will see the US Midway, Sea port Village, the Rady shell and we might... More
Private Tour

Private Day Sailing Experience in San Diego up to 12 guests
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North America
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Superb49 reviews5
This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is be....
Private Tour