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Top 10 Best USA Sailing Trips

Found 406 Sailing Trips activities in USA. Sort by Popularity. - Page 12
 

Schooner Eastwind Sunset Sail to see the Maine Coastline

(4.5 of 42 reviews)

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More

Free Cancellation
Start From $59.95
 
Schooner Eastwind Sunset Sail to see the Maine Coastline Likely to Sell Out

Schooner Eastwind Sunset Sail to see the Maine Coastline

  • USA
  • Exellent42 reviews4.5

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....

    Free Cancellation
    Start From $59.95
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 233 reviews)

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 adve... More

Free Cancellation
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • USA
  • Superb233 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....

    Free Cancellation
    Start From $136.19
 
 

Private Local Day Sail by a Certified Captain

(4.9 of 233 reviews)

Nominated Best of Baltimore Tourist Attraction 2023 & 2024 Baltimore’s authentic and top-rated private sailing experience awaits aboard Saeda, a 45-foot yacht offering a 2-hour daytime cruise through South Baltimore’s scenic ... More

Free Cancellation
Private Tour
Start From $735.00
 
Private Local Day Sail by a Certified Captain Likely to Sell Out

Private Local Day Sail by a Certified Captain

  • USA
  • Superb233 reviews4.9

Nominated Best of Baltimore Tourist Attraction 2023 & 2024 Baltimore’s authentic and top-rated pr....

    Free Cancellation
    Private Tour
    Start From $735.00
 
 

2-Hour Sunset Sailing With Wine In Stock Island

(5 of 81 reviews)

Sail with a smaller group of guests on our 65 foot schooner. Enjoy wines from around the world. Indulge in a variety of IPA, Import or domestic beers. Taste an assortment of appetizers. Enjoy a beautiful sunset while on the water.... More

Free Cancellation
Private Tour
Start From $133.89
 
2-Hour Sunset Sailing With Wine In Stock Island Likely to Sell Out

2-Hour Sunset Sailing With Wine In Stock Island

  • USA
  • Superb81 reviews5

Sail with a smaller group of guests on our 65 foot schooner. Enjoy wines from around the world. Indu....

    Free Cancellation
    Private Tour
    Start From $133.89
 
 

Afternoon or Sunset Sail On A Vintage Yacht Beer & Wine Included

(5 of 69 reviews)

Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of a 1904 gaff-rigged Friendship sloop. Her best features include highly-finished woodwork, bronze fixtures, and gaff rigging that s... More

Free Cancellation
Private Tour
Start From $115.00
 
Afternoon or Sunset Sail On A Vintage Yacht Beer & Wine Included Likely to Sell Out

Afternoon or Sunset Sail On A Vintage Yacht Beer & Wine Included

  • USA
  • Superb69 reviews5

Book an unforgettable tour with Captain Phil and sail in style aboard Liberty, a stunning replica of....

    Free Cancellation
    Private Tour
    Start From $115.00
 
 

2 Hour Sailing Lesson in Wrightsville Beach

(5 of 8 reviews)

Experience the thrill of sailing a 26' performance keelboat! Our knowledgeable captains will take you around the waterways of Wrightsville Beach and out into the Atlantic Ocean. You have the freedom to make this a learning experie... More

Free Cancellation
Private Tour
Start From $360.00
 
2 Hour Sailing Lesson in Wrightsville Beach Likely to Sell Out

2 Hour Sailing Lesson in Wrightsville Beach

  • USA
  • Superb8 reviews5

Experience the thrill of sailing a 26' performance keelboat! Our knowledgeable captains will take yo....

    Free Cancellation
    Private Tour
    Start From $360.00
 
 

6-Hour Sailing Charter from Fort Lauderdale

(5 of 3 reviews)

Enjoy some time on the water with this 6-Hour Full Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option to use their time docked or sailing out to sea. Once on the water... More

Free Cancellation
Private Tour
Start From $400.00
 
6-Hour Sailing Charter from Fort Lauderdale Likely to Sell Out

6-Hour Sailing Charter from Fort Lauderdale

  • USA
  • Superb3 reviews5

Enjoy some time on the water with this 6-Hour Full Day Sailing Charter located in Fort Lauderdale. Y....

    Free Cancellation
    Private Tour
    Start From $400.00
 
 

12pm Turtle Canyon Snorkel Adventure

(4.8 of 284 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Free Cancellation
Private Tour
Start From $96.30
 
12pm Turtle Canyon Snorkel Adventure Likely to Sell Out

12pm Turtle Canyon Snorkel Adventure

  • USA
  • Superb284 reviews4.8

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Free Cancellation
    Private Tour
    Start From $96.30
 
 

Key West Ultimate Beach Pass with Parasailing

(4.2 of 21 reviews)

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass. ... More

Free Cancellation
Private Tour
Start From $109.95
 
Key West Ultimate Beach Pass with Parasailing Likely to Sell Out

Key West Ultimate Beach Pass with Parasailing

  • USA
  • Exellent21 reviews4.2

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are....

    Free Cancellation
    Private Tour
    Start From $109.95
 
 

Deluxe private Sunset & Day Sail

(5 of 1 review)

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling voyage takes you through breathtaking waters, past iconic landmarks, and into the heart of coastal paradise. Feel the wind in your... More

Free Cancellation
Private Tour
Start From $714.00
 
Deluxe private Sunset & Day Sail Likely to Sell Out

Deluxe private Sunset & Day Sail

  • USA
  • Superb1 review5

Set sail on the ultimate San Diego adventure! Departing from 955 Harbor Island Drive, our thrilling ....

    Free Cancellation
    Private Tour
    Start From $714.00
 
 

Private Catamaran: Snorkel, Swim and Dolphin Watching

(5 of 1 review)

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take you to some of the best spots the area has to offer while you are visiting the Emerald Coast. ... More

Free Cancellation
Private Tour
Start From $465.00
 
Private Catamaran: Snorkel, Swim and Dolphin Watching Likely to Sell Out

Private Catamaran: Snorkel, Swim and Dolphin Watching

  • USA
  • Superb1 review5

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion....

    Free Cancellation
    Private Tour
    Start From $465.00
 
 

Rosé Golden Hour Sunset Sail

(5 of 5 reviews)

Set sail into the sunset aboard Rosé, our 36-foot luxury sailing catamaran. This 2-hour sunset cruise offers panoramic views of the Hilton Head coastline with complimentary light bites and drinks on board. Whether you're going wi... More

Free Cancellation
Private Tour
Start From $105.93
 
Rosé Golden Hour Sunset Sail Likely to Sell Out

Rosé Golden Hour Sunset Sail

  • USA
  • Superb5 reviews5

Set sail into the sunset aboard Rosé, our 36-foot luxury sailing catamaran. This 2-hour sunset crui....

    Free Cancellation
    Private Tour
    Start From $105.93
 
 

Sunset Sail Experience by Catamaran in Waikiki

(5 of 5 reviews)

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu skyline from offshore Waikiki and feel the warmth of the setting Hawaiian sun and tropical ... More

Free Cancellation
Private Tour
Start From $92.31
 
Sunset Sail Experience by Catamaran in Waikiki Likely to Sell Out

Sunset Sail Experience by Catamaran in Waikiki

  • USA
  • Superb5 reviews5

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....

    Free Cancellation
    Private Tour
    Start From $92.31
 
 

SUNSET CRUISE in Key Largo,FL.

(5 of 3 reviews)

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting in long lines. Personalize the trip to your liking. A private charter makes it more personab... More

Free Cancellation
Private Tour
Start From $479.00
 
SUNSET CRUISE in Key Largo,FL. Likely to Sell Out

SUNSET CRUISE in Key Largo,FL.

  • USA
  • Superb3 reviews5

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need t....

    Free Cancellation
    Private Tour
    Start From $479.00
 
 

Key West Day Sail on Schooner America 2.0 with 2 Drinks

(4.9 of 188 reviews)

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean... More

Free Cancellation
Private Tour
Start From $73.10
 
Key West Day Sail on Schooner America 2.0 with 2 Drinks Likely to Sell Out

Key West Day Sail on Schooner America 2.0 with 2 Drinks

  • USA
  • Superb188 reviews4.9

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a ....

    Free Cancellation
    Private Tour
    Start From $73.10
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(5 of 15 reviews)

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! We are a 49-passenger beautiful yellow and red retired Waikiki Beach catamaran now operating from Kewalo... More

Free Cancellation
Private Tour
Start From $47.50
 
South Shore Open Sail from Kewalo Harbor Including Drinks Likely to Sell Out

South Shore Open Sail from Kewalo Harbor Including Drinks

  • USA
  • Superb15 reviews5

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....

    Free Cancellation
    Private Tour
    Start From $47.50
 
 

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

  • USA
  • 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
 
 

2-Hour Rosé Luxury Day Sail

(5 of 1 review)

This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expert captains leading the way. Keep an eye out for dolphins, seabirds, and Lowcountry landmarks as you relax, unwind, and enjoy the ... More

Free Cancellation
Private Tour
Start From $74.97
 
2-Hour Rosé Luxury Day Sail Likely to Sell Out

2-Hour Rosé Luxury Day Sail

  • USA
  • Superb1 review5

This 2-hour daytime sail offers a smooth, spacious ride through the scenic Calibogue Sound with expe....

    Free Cancellation
    Private Tour
    Start From $74.97
 
 

Let's Go Sail the York River in Gloucester Point, Virginia

(5 of 122 reviews)

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern conveniences. Or sit back and relax in the cockpit or up on the bow of the boat for greater privacy. Great idea for engagement, bi... More

Free Cancellation
Private Tour
Start From $96.42
 
Let's Go Sail the York River in Gloucester Point, Virginia Likely to Sell Out

Let's Go Sail the York River in Gloucester Point, Virginia

  • USA
  • Superb122 reviews5

Couples and families enjoy a unique opportunity to sail their own 32-foot sloop with all the modern ....

    Free Cancellation
    Private Tour
    Start From $96.42
 
 

Sunset and Afternoon Sailing Tours Aboard A Vintage Yacht

(5 of 2 reviews)

This unforgettable 2.5 hour tour will circle you around the San Diego harbor during the most dramatic part of a California day. The multi-colored sky is the perfect backdrop for relaxing and enjoying our complimentary beer and win... More

Free Cancellation
Private Tour
Start From $135.00
 
Sunset and Afternoon Sailing Tours Aboard A Vintage Yacht Likely to Sell Out

Sunset and Afternoon Sailing Tours Aboard A Vintage Yacht

  • USA
  • Superb2 reviews5

This unforgettable 2.5 hour tour will circle you around the San Diego harbor during the most dramati....

    Free Cancellation
    Private Tour
    Start From $135.00
 
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