Day Sail Aboard Schooner America 2.0 by Classic Harbor Line

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Explore the high seas in style on the Schooner America 2.0, namesake of the first sailboat to win the America's Cup in 1851, with Classic Harbor Line. This stunning 105-foot sailboat features teak decks, mahogany trimmings and ample seating for the whole family. The sights you’ll see along the way include a waterside view of Fort Zachary Taylor, the famed Sand Key Lighthouse, Mallory Square, and Sunset Pier. So sit back and feel the warm breeze dance across your skin as you watch the sights on the beautiful waters of Key West.

Activity Highlights

  • Sail the surf in search of marine wildlife and fantastic scenery
  • Complimentary beer, wine, champagne, and soft drinks provided
  • Take a turn at the helm of one of the fastest schooners in the United States
  • Snack on delicious hors d'oeuvres while you sail
  • The crew is First Aid, CPR & AED certified.

What's Included

  • Complimentary beer, wine, champagne, and soft drinks
  • Small hors d'oeuvres platter
  • Life jackets
  • Delicious Bloody Marys for purchase (credit card only)

What to bring

  • Sunscreen
  • Weather appropriate clothing
  • Towel
  • Hat
  • Camera
  • Customers may bring a picnic or snacks
  • Reasonable sized carry-on bags are permitted


  • No glass bottles.
  • No outside alcohol allowed on board.
  • Must be 21 or older to consume alcoholic beverages.
  • Gratuities are not included.

Additional information

  • Parking is available nearby for a fee.
  • Not handicap accessible
  • Restrooms available
  • Certified service animals OK
  • A standard gratuity of 15-20% is recommended.

Cancellation policy

Tickets are non-refundable unless the captain cancels on account of weather.

Check Availability/Book online

Read what other TripShock! travelers think about the Day Sail Aboard Schooner America 2.0 by Classic Harbor Line. What they loved, what they liked and what they think could be improved, it's all here to help you make the most of your next trip. Only TripShock! customers may leave reviews. Please login to your reservation to post your review.

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  • Beth Brodd USA about 7 months ago


    Verified TripShock! Traveler Review
  • John Wold USA about 7 months ago

    Excellent Sail!

    We had a fabulous sail with our all female crew of Amber Heather and Mary! Very fun and knowledgeable as well as excellent sailors! The boat was gorgeous! The allotted time went way too fast...We will certainly go out again on next trip to the Keys!

    Verified TripShock! Traveler Review
  • Elizabeth Pille San Diego about 7 months ago

    Great Day on the Water

    Wonderful experience sailing with this all female crew under the guidance of Captain Amber...cheerful, knowledgeable and welcoming ... they taught us safety and all about the coral reef!

    Verified TripShock! Traveler Review
  • David L. Greenfield USA about 7 months ago


    Verified TripShock! Traveler Review
  • Mary Bet Beaulieu USA about 9 months ago

    Gorgeous sailing ship, amazing crew!

    Highly recommend! The crew was professional and just a lot of fun. The boat is spotlessly clean. I have never sailed. This was a great introduction. I enjoyed every minute. I wish I could remember the names of the crew who worked with Captain Ron. They deserve a shout out!!! Smart women, passionate about their work. And did I say fun????

    Verified TripShock! Traveler Review
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