Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 725 Sailing Trips activities in North America. Sort by Popularity. - Page 12Small Group Waikiki Sunset Sailing Tour
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More

Small Group Waikiki Sunset Sailing Tour
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North America
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Superb109 reviews4.9
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....
ATV's at Stone Island with Horse Ride, Water Sports, Food & Drink
Welcome to the Beach Club All-Inclusive, where we believe in the power of adventure and the beauty of the beach. We are the ultimate vacation destination, providing the guests with an adrenaline-fueled experience like no other. Ge... More

ATV's at Stone Island with Horse Ride, Water Sports, Food & Drink
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North America
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Superb109 reviews4.9
Welcome to the Beach Club All-Inclusive, where we believe in the power of adventure and the beauty o....

Luxury Camden Sailing Experience
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North America
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Superb9 reviews5
Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Faste....

Private Guided Sunset and Eco Tour up to 6 Passengers
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a cooler with bottled water a... More
Free Cancellation
Private Tour
(Saving 15% )

Private Guided Sunset and Eco Tour up to 6 Passengers
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North America
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Superb74 reviews5
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....
Free Cancellation
Private Tour
(Saving 15% )
Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach
Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island Swim & Sunset Cruises. Enjoy your Island Sandbar stop at One Tree Island, where you can enjoy the beautiful waters... More
Private Tour

Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach
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North America
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Superb51 reviews4.7
Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Do....
Private Tour
Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline
Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Miami Beach experience. Connect with nature, discover new landscapes, & create lasting memories as you explore the stunning coastline... More
Private Tour

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline
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North America
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Superb23 reviews4.8
Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Mia....
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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Superb100 reviews5
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....
Private Tour
Let’s do a morning sail on San Francisco Bay (semi private)
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

Let’s do a morning sail on San Francisco Bay (semi private)
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North America
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Superb6 reviews5
Have you ever wanted to go sailing in the San Francisco Bay area but didn’t know anyone with a boa....
Private Tour
Skagway Trail and Sail
This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike Electric Bicycles where you will join us for a self-guided ride to some of Skagway's best sites! You will visit a waterfall, scenic... More
Private Tour

Skagway Trail and Sail
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North America
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Superb5 reviews4.8
This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike E....
Private Tour
2-hour Private Luxury New York City Sunset Boat Tour
Experience the breathtaking beauty of New York City as the sun sets behind the Statue of Liberty and reflects off of the city skyline on this magical 2-hour sunset cruise around lower Manhattan! Get an unobstructed view of the Man... More
Private Tour

2-hour Private Luxury New York City Sunset Boat Tour
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North America
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Superb28 reviews5
Experience the breathtaking beauty of New York City as the sun sets behind the Statue of Liberty and....
Private Tour
Romantic Dinner on a Spanish Galeon in Cancun
Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner with the most wonderful scenary. This is the perfect opportunity to enjoy a delicious dinner while you fall in love with the liv... More
Private Tour

Romantic Dinner on a Spanish Galeon in Cancun
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North America
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Exellent22 reviews4.2
Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner ....
Private Tour
2 Hours Holo Holo Sunset Cocktail Sail with Open Bar
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience offers breathtaking views of the sunset complemented by deligh... More
Private Tour

2 Hours Holo Holo Sunset Cocktail Sail with Open Bar
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North America
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Good2 reviews3.5
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....
Private Tour
Private Customizable Sailing Tour in Cancun
Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers the opportunity to visit wonderful places that can only be known by the sea. From a relaxing private sailing tour in the bay of Can... More
Private Tour

Private Customizable Sailing Tour in Cancun
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North America
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Superb120 reviews4.7
Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers th....
Private Tour
Private Morning Sail, Dolphin and History Tour on Mystique
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. For over 12 years, our sailing yachts are the highest quality and operated by two professional ... More
Private Tour

Private Morning Sail, Dolphin and History Tour on Mystique
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North America
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Superb83 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Golden Gate Bridge Sailing Tour
Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail off to the Golden Gate Bridge and enjoy panoramic views of the San Francisco skyline, Sausalito, Angel Island, Tiburon, and Marin... More
Private Tour

Golden Gate Bridge Sailing Tour
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North America
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Superb50 reviews4.8
Have a once-in-a-lifetime experience by sailing under and around the iconic Golden Gate Bridge. Sail....
Private Tour
Deluxe Turtle Snorkeling Escapade at Waikiki
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
Private Tour

Deluxe Turtle Snorkeling Escapade at Waikiki
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North America
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Superb7 reviews4.9
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
Private Tour
Dolphin Adventure Sail in Cocoa Beach
Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter pla... More
Private Tour

Dolphin Adventure Sail in Cocoa Beach
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North America
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Superb160 reviews4.9
Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....
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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Superb228 reviews4.8
Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for ....
Private Tour

Sailing Snorkel Adventure
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North America
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Exellent6 reviews4.5
Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sa....
Private Tour
BYOB Friday Night Fireworks Cruise
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More
Private Tour

BYOB Friday Night Fireworks Cruise
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North America
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Exellent6 reviews4.3
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....
Private Tour