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Top 10 Best North America Sailing Trips

Found 643 Sailing Trips activities in North America. Sort by Popularity. - Page 5
 

4-Hour Fort Lauderdale Sailing Charter

(4.9 of 266 reviews)

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More

Free Cancellation
Start From $165.00
 
4-Hour Fort Lauderdale Sailing Charter

4-Hour Fort Lauderdale Sailing Charter

  • North America
  • Superb266 reviews4.9

Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Start From $165.00
 
 

Dolphin Catamaran Day Sail in Merritt Island

(5 of 122 reviews)

Set sail on a unique, small-group Dolphin Catamaran Day Sail and experience the best of the Cocoa Beach area! This tour offers an unforgettable combination of dolphin watching, scenic views, and relaxation. What makes this tour s... More

Free Cancellation
Start From $50.85
 
Dolphin Catamaran Day Sail in Merritt Island

Dolphin Catamaran Day Sail in Merritt Island

  • North America
  • Superb122 reviews5

Set sail on a unique, small-group Dolphin Catamaran Day Sail and experience the best of the Cocoa Be....

    Free Cancellation
    Start From $50.85
 
 

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

(4.9 of 102 reviews)

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

Free Cancellation
Start From $70.00
 
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

  • North America
  • Superb102 reviews4.9

Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....

    Free Cancellation
    Start From $70.00
 
 

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani

(4.8 of 35 reviews)

Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. This 1.5-hour journey from Honokohau Harbor offers a chance to bask in the sun and enjoy the ocean breeze while taking in the breath... More

Free Cancellation
Start From $117.76
 
Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani

  • North America
  • Superb35 reviews4.8

Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. Th....

    Free Cancellation
    Start From $117.76
 
 

Small-Group San Diego Afternoon Sailing Excursion

(5 of 477 reviews)

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing you a comfortable, semi-private experience (or, grab five friends and fill up the whole boat!). Sit back, relax and enjoy the com... More

Free Cancellation
Start From $116.00
 
Small-Group San Diego Afternoon Sailing Excursion Likely to Sell Out

Small-Group San Diego Afternoon Sailing Excursion

  • North America
  • Superb477 reviews5

This three-hour adventure on a a beautiful modern-day sailboat is limited to just 6 people, allowing....

    Free Cancellation
    Start From $116.00
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(4.9 of 7 reviews)

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 ‘Honu’. A hot buff... More

Free Cancellation
Start From $172.85
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui Likely to Sell Out

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • North America
  • Superb7 reviews4.9

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....

    Free Cancellation
    Start From $172.85
 
 

2-Hour Private Sailing Experience in San Diego Bay

(5 of 139 reviews)

Our unique sail displays a peace sign because that is exactly what we share with our customers, peace. Peace is not always an easy thing to obtain in today's world. With all the stress life brings we are happy to provide a peacefu... More

Special Offer
Free Cancellation
Private Tour
Start From $526.50
(Saving 10% ) $585.00
 
-10% 2-Hour Private Sailing Experience in San Diego Bay Likely to Sell Out

2-Hour Private Sailing Experience in San Diego Bay

  • North America
  • Superb139 reviews5

Our unique sail displays a peace sign because that is exactly what we share with our customers, peac....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $526.50
    (Saving 10% ) $585.00
 
 

2.5 Hours of Fun: Catamaran Sunset Sail

(4.9 of 129 reviews)

Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and lounging around watching sea life, and water rush by. The swift and stable ocean design ensures a comfortable, and exhilarating ride wit... More

Free Cancellation
Private Tour
Start From $119.00
 
2.5 Hours of Fun: Catamaran Sunset Sail Likely to Sell Out

2.5 Hours of Fun: Catamaran Sunset Sail

  • North America
  • Superb129 reviews4.9

Catamarans really are more fun to sail with the special bow nets designed for sunbathing, and loungi....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Key West's Favorite Afternoon Dolphin Sail

(4.6 of 17 reviews)

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More

Free Cancellation
Private Tour
Start From $59.00
 
Key West's Favorite Afternoon Dolphin Sail Likely to Sell Out

Key West's Favorite Afternoon Dolphin Sail

  • North America
  • Superb17 reviews4.6

Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....

    Free Cancellation
    Private Tour
    Start From $59.00
 
 

2 hour Tiki Pub Sensational Sunset Cruise (Adults only)

(4.9 of 36 reviews)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More

Free Cancellation
Private Tour
Start From $69.95
 
2 hour Tiki Pub Sensational Sunset Cruise (Adults only) Likely to Sell Out

2 hour Tiki Pub Sensational Sunset Cruise (Adults only)

  • North America
  • Superb36 reviews4.9

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....

    Free Cancellation
    Private Tour
    Start From $69.95
 
 

Champagne Sunset Cruise in Ft. Lauderdale

(4.7 of 599 reviews)

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

Free Cancellation
Private Tour
Start From $89.00
 
Champagne Sunset Cruise in Ft. Lauderdale Likely to Sell Out

Champagne Sunset Cruise in Ft. Lauderdale

  • North America
  • Superb599 reviews4.7

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Nights of Lights Viewing with Drinks and Live Music Sunset Sail

(4.8 of 6 reviews)

Come celebrate the magic of the Nights of Lights celebration with us from the water! You will see Historic St. Augustine from a whole new vantage point. It is a sight you won't soon forget. After enjoying a breathtaking sunset you... More

Free Cancellation
Private Tour
Start From $69.17
 
Nights of Lights Viewing with Drinks and Live Music Sunset Sail Likely to Sell Out

Nights of Lights Viewing with Drinks and Live Music Sunset Sail

  • North America
  • Superb6 reviews4.8

Come celebrate the magic of the Nights of Lights celebration with us from the water! You will see Hi....

    Free Cancellation
    Private Tour
    Start From $69.17
 
 

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

(4.6 of 416 reviews)

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by the famous Dennis Connor. All trips take place under full sail. We only use our motor to get in a... More

Free Cancellation
Private Tour
Start From $52.95
 
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head Likely to Sell Out

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

  • North America
  • Superb416 reviews4.6

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, S....

    Free Cancellation
    Private Tour
    Start From $52.95
 
 

Sailing Charters in Wilmington

(5 of 140 reviews)

After a successful first season I am happy to be here for back to back seasons. Sail in style on the historic Wilmington river walk. Enjoy a personalized Charter experience with up to six guests. Very few sailboats are up for publ... More

Free Cancellation
Private Tour
Start From $89.00
 
Sailing Charters in Wilmington Likely to Sell Out

Sailing Charters in Wilmington

  • North America
  • Superb140 reviews5

After a successful first season I am happy to be here for back to back seasons. Sail in style on the....

    Free Cancellation
    Private Tour
    Start From $89.00
 
 

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

(4.8 of 80 reviews)

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Free Cancellation
Private Tour
Start From $34.99
 
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast Likely to Sell Out

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

  • North America
  • Superb80 reviews4.8

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....

    Free Cancellation
    Private Tour
    Start From $34.99
 
 

El Cielo Cozumel Snorkeling by Private Boat

(4.8 of 128 reviews)

TRAVELER'S FAVORITE EXPERIENCE! Have fun aboard your Private boat and experience Cozumel water treasures in this incredible snorkeling adventure. This 4 hours family-friendly Private tour will take you out to the most renowned r... More

Free Cancellation
Private Tour
Start From $789.00
 
El Cielo Cozumel Snorkeling by Private Boat Likely to Sell Out

El Cielo Cozumel Snorkeling by Private Boat

  • North America
  • Superb128 reviews4.8

TRAVELER'S FAVORITE EXPERIENCE! Have fun aboard your Private boat and experience Cozumel water trea....

    Free Cancellation
    Private Tour
    Start From $789.00
 
 

Exclusive Isla Mujeres and Cancun Private Yacht Tour

(4.9 of 21 reviews)

Embark on an unforgettable yacht adventure in Cancun and Isla Mujeres, where turquoise waters set the stage for a day of exhilaration and relaxation. Cruise along the mesmerizing Cancun coastlines, dive into vibrant coral reefs du... More

Free Cancellation
Private Tour
Start From $720.00
 
Exclusive Isla Mujeres and Cancun Private Yacht Tour Likely to Sell Out

Exclusive Isla Mujeres and Cancun Private Yacht Tour

  • North America
  • Superb21 reviews4.9

Embark on an unforgettable yacht adventure in Cancun and Isla Mujeres, where turquoise waters set th....

    Free Cancellation
    Private Tour
    Start From $720.00
 
 

New York City Sunset Jazz Sail aboard Clipper City

(4.4 of 98 reviews)

Watch night fall on the city as the sun sets behind the Statue of Liberty from the unbeatable vantage point of the harbor. Order a drink from our full bar as we raise canvas and leave Manhattan behind as the melodies of live jazz ... More

Free Cancellation
Private Tour
Start From $104.00
 
New York City Sunset Jazz Sail aboard Clipper City Likely to Sell Out

New York City Sunset Jazz Sail aboard Clipper City

  • North America
  • Exellent98 reviews4.4

Watch night fall on the city as the sun sets behind the Statue of Liberty from the unbeatable vantag....

    Free Cancellation
    Private Tour
    Start From $104.00
 
 

Waikiki Fireworks Cocktail Cruise

(4 of 3 reviews)

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to remember. ... More

Free Cancellation
Private Tour
Start From $85.09
 
Waikiki Fireworks Cocktail Cruise Likely to Sell Out

Waikiki Fireworks Cocktail Cruise

  • North America
  • Very Good3 reviews4

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....

    Free Cancellation
    Private Tour
    Start From $85.09
 
 

Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboard

(4.8 of 181 reviews)

• Enjoy the turquoise waters of Cozumel aboard one of our luxury sailing catamarans. • Snorkel and marvel at the wide array of tropical fish and rich marine life that inhabit the colorful reefs of the island. • Paddleboard a... More

Free Cancellation
Private Tour
Start From $139.00
 
Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboard Likely to Sell Out

Cozumel Luxury Sailing & Snorkeling with Lunch and Open Bar Onboa....

  • North America
  • Superb181 reviews4.8

• Enjoy the turquoise waters of Cozumel aboard one of our luxury sailing catamarans. • Snorkel a....

    Free Cancellation
    Private Tour
    Start From $139.00
 
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