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Top 10 Best USA Sailing Trips

Found 428 Sailing Trips activities in USA. Sort by Popularity. - Page 8
 

Waikoloa Catamaran Snorkel Sail Including Lunch

(4.6 of 104 reviews)

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy a smooth, comfortable ride to one of the region’s best sno... More

Free Cancellation
Start From $189.95
 
Waikoloa Catamaran Snorkel Sail Including Lunch

Waikoloa Catamaran Snorkel Sail Including Lunch

  • USA
  • Superb104 reviews4.6

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautif....

    Free Cancellation
    Start From $189.95
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 530 reviews)

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

Free Cancellation
Start From $177.73
 
Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

  • USA
  • Superb530 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....

    Free Cancellation
    Start From $177.73
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 469 reviews)

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... More

Free Cancellation
Start From $179.27
 
Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

  • USA
  • Superb469 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....

    Free Cancellation
    Start From $179.27
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.8 of 58 reviews)

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More

Free Cancellation
Start From $179.00
 
Hawaiian Canoe Sailing Experience in Maui

Hawaiian Canoe Sailing Experience in Maui

  • USA
  • Superb58 reviews4.8

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Free Cancellation
    Start From $179.00
 
 

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

(4.9 of 164 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 $79.50
 
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans

  • USA
  • Superb164 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 $79.50
 
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 101 reviews)

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More

Free Cancellation
Start From $309.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • USA
  • Superb101 reviews4.9

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....

    Free Cancellation
    Start From $309.00
 
 

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

(5 of 84 reviews)

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More

Free Cancellation
Start From $149.00
 
2hr. INTERACTIVE Sailing Experience on San Francisco Bay Likely to Sell Out

2hr. INTERACTIVE Sailing Experience on San Francisco Bay

  • USA
  • Superb84 reviews5

This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....

    Free Cancellation
    Start From $149.00
 
 

4-Hour St. Pete Pier to Egmont Key Experience by Ferry

(4.7 of 306 reviews)

From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stunning Sunshine Skyway bridge and perhaps see a dolphin or two! This is the only charter offering service from downtown St. Petersb... More

Free Cancellation
Start From $66.67
 
4-Hour St. Pete Pier to Egmont Key Experience by Ferry Likely to Sell Out

4-Hour St. Pete Pier to Egmont Key Experience by Ferry

  • USA
  • Superb306 reviews4.7

From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....

    Free Cancellation
    Start From $66.67
 
 

Schooner Appledore Day Sail with Full Bar in Key West

(4.9 of 84 reviews)

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More

Free Cancellation
Start From $49.00
 
Schooner Appledore Day Sail with Full Bar in Key West Likely to Sell Out

Schooner Appledore Day Sail with Full Bar in Key West

  • USA
  • Superb84 reviews4.9

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....

    Free Cancellation
    Start From $49.00
 
 

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

(5 of 42 reviews)

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and op... More

Free Cancellation
Private Tour
Start From $599.00
 
Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique Likely to Sell Out

Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

  • USA
  • Superb42 reviews5

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....

    Free Cancellation
    Private Tour
    Start From $599.00
 
 

Key West Ultimate Beach Pass with Parasailing

(4.1 of 24 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
  • Exellent24 reviews4.1

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
 
 

Private Sailing on the Miami Bay - Biscayne Bay

(4.9 of 74 reviews)

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Destino Charters Beneteau stylish vessels in the company of experienced, but mostly fun, well traveled, passionate captains. A Private Sailing tour aboard Destino ... More

Free Cancellation
Private Tour
Start From $425.00
 
Private Sailing on the Miami Bay - Biscayne Bay Likely to Sell Out

Private Sailing on the Miami Bay - Biscayne Bay

  • USA
  • Superb74 reviews4.9

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Destino Charters Beneteau stylish....

    Free Cancellation
    Private Tour
    Start From $425.00
 
 

2-Hour Sunset Sail from San Diego

(4.8 of 72 reviews)

Leave your worries behind as you cruise the San Diego Bay and marvel at the cityscape. The vibrant waterfront offers expansive views of Downtown, Point Loma, and Coronado Island. Experience the setting sun cast its brilliant color... More

Free Cancellation
Private Tour
Start From $130.00
 
2-Hour Sunset Sail from San Diego Likely to Sell Out

2-Hour Sunset Sail from San Diego

  • USA
  • Superb72 reviews4.8

Leave your worries behind as you cruise the San Diego Bay and marvel at the cityscape. The vibrant w....

    Free Cancellation
    Private Tour
    Start From $130.00
 
 

Private Dolphin Sightseeing Sail on The Daydreams Sailboat

(4.8 of 72 reviews)

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and your guests! Your 90 minute Dolphin Sightseeing Sail on our Daydreams sailboat will inclu... More

Free Cancellation
Private Tour
Start From $499.00
 
Private Dolphin Sightseeing Sail on The Daydreams Sailboat Likely to Sell Out

Private Dolphin Sightseeing Sail on The Daydreams Sailboat

  • USA
  • Superb72 reviews4.8

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you....

    Free Cancellation
    Private Tour
    Start From $499.00
 
 

Private Sunset Catamaran Sail in Cocoa Beach

(4.8 of 72 reviews)

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the bea... More

Free Cancellation
Private Tour
Start From $337.87
 
Private Sunset Catamaran Sail in Cocoa Beach Likely to Sell Out

Private Sunset Catamaran Sail in Cocoa Beach

  • USA
  • Superb72 reviews4.8

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a....

    Free Cancellation
    Private Tour
    Start From $337.87
 
 

Sunset Cocktail Cruise on our Sailing Catamaran

(4.8 of 62 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More

Free Cancellation
Private Tour
Start From $165.00
 
Sunset Cocktail Cruise on our Sailing Catamaran Likely to Sell Out

Sunset Cocktail Cruise on our Sailing Catamaran

  • USA
  • Superb62 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

Sunset Sail in the Gulf of Mexico for up to 6 Guests

(5 of 6 reviews)

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the sun dips below the horizon. For two and a half hours, enjoy the stunning views along Fort ... More

Free Cancellation
Private Tour
Start From $149.00
 
Sunset Sail in the Gulf of Mexico for up to 6 Guests Likely to Sell Out

Sunset Sail in the Gulf of Mexico for up to 6 Guests

  • USA
  • Superb6 reviews5

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the roman....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

(4.8 of 20 reviews)

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ... More

Free Cancellation
Private Tour
Start From $91.23
 
Sail on Tall Ship Windy, join us for our Likely to Sell Out

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

  • USA
  • Superb20 reviews4.8

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This ....

    Free Cancellation
    Private Tour
    Start From $91.23
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(5 of 21 reviews)

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have complimentary drinks (alcoholic beverages available for adults 21+ with valid ID o... 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
  • Superb21 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
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.7 of 31 reviews)

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More

Free Cancellation
Private Tour
Start From $156.79
 
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch Likely to Sell Out

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • USA
  • Superb31 reviews4.7

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....

    Free Cancellation
    Private Tour
    Start From $156.79
 
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