Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 668 Sailing Trips activities in North America. Sort by Popularity. - Page 2Leila 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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Superb462 reviews4.7
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....
Key West Snorkeling with Breakfast and Unlimited Mimosas
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More

Key West Snorkeling with Breakfast and Unlimited Mimosas
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North America
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Exellent506 reviews4.5
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....
Sunset Sail in Key West with Beverages Included
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More

Sunset Sail in Key West with Beverages Included
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North America
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Superb795 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
Na Pali Coast Kauai Snorkel and Sail
Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and comfortable 50’ Kauai-built sailing catamaran, Leila. Let’s explore the cliffs, valleys, sea caves and wildlife of the Napali... More

Na Pali Coast Kauai Snorkel and Sail
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North America
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Superb509 reviews4.8
Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and....
Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club
Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among vibrant tropical fish, then relax on Playa Norte, one of Mexico's finest beaches. Departing from the pier, begin with a 30-minut... More

Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club
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North America
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Superb99 reviews4.7
Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among ....
Oahu Catamaran Waikiki Sunset on 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 Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
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North America
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Superb621 reviews4.9
AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE C....
Cabo San Lucas Sunset Sailing Shared Cruise
Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated at night, and see the wonderful sunset contrasting with Cabo San Lucas amazing waters. This is a family-friendly tour and includes... More

Cabo San Lucas Sunset Sailing Shared Cruise
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North America
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Superb709 reviews4.9
Enjoy a 2-hour sunset cruise aboard a beautiful luxury sailing boat. Admire the sights illuminated ....
Private Luxury Sailing Charters, BYOB & Dolphins
We are a family owned luxury sailing charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the water on one of our sailboats. We offer hourly, daily, or customized tours according to y... More
Private Tour

Private Luxury Sailing Charters, BYOB & Dolphins
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North America
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Superb351 reviews5
We are a family owned luxury sailing charter business. Come enjoy a BYOB day of sailing and seeing t....
Private Tour
Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling a... More
Private Tour

Afternoon Sail & Snorkel to the Captain Cook Monument
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North America
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Superb671 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....
Private Tour
Small-Group Sunset Sailing Experience on San Diego Bay
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
Private Tour

Small-Group Sunset Sailing Experience on San Diego Bay
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North America
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Superb543 reviews4.9
Enjoy an evening sailing under the sunset on a relaxing sailing cruise with a unique perspective on ....
Private Tour
Waikiki Sunset Cocktail Sail with Open Bar
This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruise! Strangers become fast friends on this one regardless if your cruising solo or with a crew! We provide juice, soda, bottled wate... More
Private Tour

Waikiki Sunset Cocktail Sail with Open Bar
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North America
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Superb474 reviews4.8
This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....
Private Tour
Turtles & Tacos Luxury Catamaran Snorkel
As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are eager to guide you on an unforgettable journey. The vessel is equipped with all the amenities you need for a comfortable and enjoy... More
Private Tour

Turtles & Tacos Luxury Catamaran Snorkel
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North America
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Superb20 reviews4.8
As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are ....
Private Tour
Cabo San Lucas Private catamaran Tour for Six People
Have your own private boat to cruise, snorkel, relax at the beach or swim in different places of the beautiful bay of Cabo San Lucas. Visit all landmarks such as the arch, sea lion colony, neptunes finger, lovers beach, divorc... More
Private Tour

Cabo San Lucas Private catamaran Tour for Six People
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North America
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Superb294 reviews4.9
Have your own private boat to cruise, snorkel, relax at the beach or swim in different places of t....
Private Tour
Deluxe Sail & Snorkel to the Captain Cook Monument
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters a... More
Private Tour

Deluxe Sail & Snorkel to the Captain Cook Monument
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North America
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Superb461 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....
Private Tour

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More
Free Cancellation
Private Tour
(Saving 15% )

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
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North America
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Superb206 reviews4.9
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....
Free Cancellation
Private Tour
(Saving 15% )
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More
Private Tour

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
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North America
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Superb132 reviews4.9
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....
Private Tour
Kona-Kohala Coast Sunset Sail by Catamaran
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon. You may even see the green flash. Board from Anaehoomalu Bay (A-Bay) to sail... More
Private Tour

Kona-Kohala Coast Sunset Sail by Catamaran
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North America
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Superb341 reviews4.7
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....
Private Tour
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
Private Tour

Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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North America
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Superb783 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Private Tour
El Cielo, Palancar Snorkel & Beach Party Experience
El Cielo is an unspoiled, natural marvel of cobalt crystal clear shallow waters, sand bottom, and Cozumel's jungle in the background; we will relax here after snorkeling at the world famous Palancar Reef offers to snorkelers a col... More
Private Tour

El Cielo, Palancar Snorkel & Beach Party Experience
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North America
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Superb502 reviews4.7
El Cielo is an unspoiled, natural marvel of cobalt crystal clear shallow waters, sand bottom, and Co....
Private Tour
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy ... More
Private Tour

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
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North America
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Superb1,215 reviews4.9
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....
Private Tour