Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 723 Sailing Trips activities in North America. Sort by Popularity. - Page 32Sunset Boat Tour Includes Open Bar and Dinner
No trip to Cabo is complete with a sunset boat tour of the world famous arch. This is the sunset boat tour that covers all of your bucket list checks! Open bar, light food, a sunset boat tour and memories to last a lifetime!... More
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Sunset Boat Tour Includes Open Bar and Dinner
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North America
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Good2 reviews3.5
No trip to Cabo is complete with a sunset boat tour of the world famous arch. This is the sunset boa....
Free Cancellation
(Saving 20% )
Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay
This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become part of the crew. Our goal is to perform as a unit and get the boat to sail as fast as possible. However, if you are looking for a mo... More
Private Tour

Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay
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North America
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Good2 reviews3.5
This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become par....
Private Tour
Private Luxury Yacht in Miami
️ Luxury Sea Ray Sundancer 33’ – Miami’s Ultimate Boating Experience! ️ Cruise Miami’s top destinations—Haulover Sandbar, Oleta River State Park, Biscayne Bay & Sands Key, and Raccoon Island—in style! This sleek 3... More
Private Tour

Private Luxury Yacht in Miami
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North America
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Good2 reviews3.5
️ Luxury Sea Ray Sundancer 33’ – Miami’s Ultimate Boating Experience! ️ Cruise Miami’s ....
Private Tour
Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 passengers
Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you explore stunning sites and Caribbean reefs. Experience the magic of the Mexican Caribbean, snorkeling in Isla Mujeres and Cancun's ... More
Private Tour

Private Snorkeling and Sightseeing Catamaran Boat Tour Deluxe 36 ....
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North America
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Good2 reviews3.5
Embark on a breathtaking sailing adventure from Cancun to Isla Mujeres. Feel the excitement as you e....
Private Tour
Private Charter Snorkel Sail Adventure off Kaanapali Beach
PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘H... More
Private Tour

Private Charter Snorkel Sail Adventure off Kaanapali Beach
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North America
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Good2 reviews3.5
PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....
Private Tour
Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs
Welcome to the coast of Puerto Vallarta, a luxury destination known for its variety of exciting nautical activities! If you are looking to live a unique and unforgettable experience with family or friends, this is the perfect plac... More
Private Tour

Luxury Sailboat 50 feet in Private for up to 9 People 4 hrs
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North America
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Good2 reviews3.5
Welcome to the coast of Puerto Vallarta, a luxury destination known for its variety of exciting naut....
Private Tour
Private Isla Mujeres Adventure & Free Time
If you are looking for the tropical getaway of your dreams, then get ready to discover Isla Mujeres, the women’s Island. Your day starts with a transfer to the dock, where your guide will take you out by boat to the island of ... More
Private Tour

Private Isla Mujeres Adventure & Free Time
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North America
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Superb12 reviews4.9
If you are looking for the tropical getaway of your dreams, then get ready to discover Isla Mujeres,....
Private Tour
Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks
Set sail on a midday escape where cocktails meet culture aboard Maui’s most luxurious sailing catamaran. Explore the island through authentic storytelling, coastal beauty, and handcrafted island specialties, both sippable and sa... More
Private Tour

Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks
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North America
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Superb1 review5
Set sail on a midday escape where cocktails meet culture aboard Maui’s most luxurious sailing cata....
Private Tour
Private Swim and Sail Charter (Kewalo Harbor)
A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). This experience is customization in its duration and activity *Viewing marine life is not guaranteed but we do... More
Private Tour

Private Swim and Sail Charter (Kewalo Harbor)
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North America
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Superb1 review5
A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and....
Private Tour
Land’s End Sunset Cruise – Open Bar & Tacos Included
Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, with approximately 40 minutes spent at each captivating point along the route. As you glide through the stunning landscapes of Cab... More
Private Tour

Land’s End Sunset Cruise – Open Bar & Tacos Included
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North America
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Superb1 review5
Embark on a serene journey aboard the CaboMar Catamaran, where each moment unfolds in tranquility, w....
Private Tour
Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran
Step aboard the elegant Tropicat and escape into a world of tranquility and beauty. As we gently sail through the stunning waters of Los Cabos, immerse yourself in breathtaking views at every turn — from the iconic Lover’s Bea... More
Private Tour

Sail into Serenity Tropical Jazz & Wine Aboard a Catamaran
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North America
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Superb1 review5
Step aboard the elegant Tropicat and escape into a world of tranquility and beauty. As we gently sai....
Private Tour
Private 43' Azimut Yacht 4h – Drinks & Food Included
What truly sets this tour apart is the level of privacy and customization we offer. Whether you're celebrating a special occasion or simply seeking a luxurious escape, our crew tailors every detail to your preferences — from the... More
Private Tour

Private 43' Azimut Yacht 4h – Drinks & Food Included
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North America
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Superb6 reviews5
What truly sets this tour apart is the level of privacy and customization we offer. Whether you're c....
Private Tour
Private Luxury Yacht for up to 12 people
A whole nautical experience awaits you on board the Sea Ray 440, nothing is missing, comfortable, luxurious and sophisticated, it is specially designed to satisfy the demands of the best tastes and turn moments into memories that ... More
Private Tour

Private Luxury Yacht for up to 12 people
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North America
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Superb6 reviews5
A whole nautical experience awaits you on board the Sea Ray 440, nothing is missing, comfortable, lu....
Private Tour
Chesapeake Bay Private Cruise
This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guys day out on the water, or just to have the cruise to yourself! Enjoy the peaceful sounds of the waves gently breaking off the hul... More
Private Tour

Chesapeake Bay Private Cruise
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North America
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Exellent7 reviews4.4
This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guy....
Private Tour
Waikiki private Day Tour and Sunset sail for couples
Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples on their honeymoon, celebrating an Anniversary, or just in love, celebrating ... More
Private Tour

Waikiki private Day Tour and Sunset sail for couples
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North America
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Superb16 reviews5
Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This privat....
Private Tour
Private 3 hour Bird Watching Tour in Monterey Bay
Enjoy a 3 hour cruise to search for and see local seabirds of the Monterey Bay. A vessel under sail is much quieter and therefore up close encounters with seabirds are common. This tour is great for birders who are looking for an ... More
Private Tour

Private 3 hour Bird Watching Tour in Monterey Bay
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North America
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Superb1 review5
Enjoy a 3 hour cruise to search for and see local seabirds of the Monterey Bay. A vessel under sail ....
Private Tour
Private Dolphin Catamaran Sail In Cocoa Beach
Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter playful dolph... More
Private Tour

Private Dolphin Catamaran Sail In Cocoa Beach
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North America
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Superb1 review5
Experience the Magic of Cocoa Beach with Our Dolphin Tour! Join Cocoa Beach Catamaran for an unforg....
Private Tour
Two Hour Private Sailing Charter
Escape the city on a two hour private sailing charter for up to 6 guests. Our two hour charter option is available morning, afternoon, and evening, and it is a great option for a quick getaway. We sail you around lower Manhattan w... More
Private Tour

Two Hour Private Sailing Charter
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North America
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Superb3 reviews5
Escape the city on a two hour private sailing charter for up to 6 guests. Our two hour charter optio....
Private Tour
Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guests
A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sailing charters and boat tours. Sail San Diego with us. Our sa... More
Private Tour

Sailing Charter Sightseeing Cruise on San Diego Bay up to 6 Guest....
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North America
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Good2 reviews3.5
A Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San D....
Private Tour
Unlimited Catamaran to Isla Mujeres from Cancun
Your journey begins at the breathtaking Punta Sam Reef, where you'll dive into your first snorkeling experience and discover the vibrant underwater world of the Caribbean. Then, set sail along the stunning coastline toward Punta... More
Private Tour

Unlimited Catamaran to Isla Mujeres from Cancun
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North America
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Good2 reviews3.5
Your journey begins at the breathtaking Punta Sam Reef, where you'll dive into your first snorkeling....
Private Tour