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“Fun and a Great Value”

Classic Harbor Line
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US$59.12*
and up
Classic Day Sail Aboard America 2.0
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US$91.38*
and up
Key West Sunset Sail Aboard Schooner America 2.0
Ranked #4 of 291 Tours in Key West
Certificate of Excellence
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Attraction details
Owner description: Classic Harbor Line, operating renowned day sail operations in Newport, RI, New York City, Boston,MA, Hoboken,NJ,and bring the glorious America 2.0 to Key West, Florida. The 105-foot, 1800s vessel is captained by US Coast Guard certified captains and only the most professional and courteous crew you will ever meet. America 2.0 is truly the diamond shining amongst the Key West Schooner Fleet. She is a close cousin to Key West's former pride, Schooner America. Guests are sure to have a comfortable ride on this fast and lively schooner. Dedicated to providing the most perfect hospitality and sailing experience one could find in Key West, Classic Harbor Line hopes for the privilege of escorting you on a breathtaking excursion aboard the most elegant vessels in the local Key West fleet: Schooner America 2.0. While visiting Key West, Florida you will find a number of land and water based activities. However, a classic schooner sail, whether it be a day sail, or sunset sail, is well known to be the quintessential Key West activity that will highlight your stay and be the lasting memory forever.
Useful Information: Activities for older children
Reviewed 20 March 2014

We were in Key West for a few hours as a stop on a cruise. Having been to Key West a bunch of times we were looking for something a little different so we jumped on the America 2.0 at the last minute for a 1.5 hour afternoon cruise. WOW! What a beautiful, educational and fun experience for adults and kids (ages 11 and 13) alike. Sailboats can be boring to some, especially when the wind is slow, but on this gorgeous windy day we had a great time. Kids were allowed to help the crew raise the sails and steer the boat and an exciting time was had by all. Both the captain and crew were extremely welcoming and friendly. You can tell they enjoy their jobs and mingling with the customers. Considering they offer unlimited drinks (including adult beverages) the price is very reasonable for this high quality experience.

1  Thank TravelCheapskate
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
CHL745, Manager at Classic Harbor Line, responded to this reviewResponded 21 April 2014

Hello,

Yes, Sailing aboard the schooner America 2.0 is really something else. It was designed so that in the lightest of wind you will feel the sailing experience!
We are happy to hear that you had a great day and that your children enjoyed it as well!
We hope to have you out with us again in Key West and if not then in one of our other locations!

Classic Harbor Line

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Reviews (1,031)
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600 - 604 of 1,031 reviews

Reviewed 20 March 2014

The sunset was a bit disappointing due to clouds but the staff more than made up for that. The view of the private island that Oprah rented (how did she get all those homeowners to agree to that?) for her friend Maya Angelou's birthday (if it's true?) is a place anyone would want to live. Gorgeous homes. The keys are quit unusual and this view is highly recommended to get the real feel of Key West.

Thank amberdamber
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
CHL745, Manager at Classic Harbor Line, responded to this reviewResponded 21 April 2014

Hello,

We are sorry to hear that it was a bit cloudy, but we are happy to hear that you enjoyed the sail as well as the company of the Crew! We love hearing feedback on them as we know they work hard and love what they do!
We hope to have you out again! If not in Key West then in one of our other locations.

Classic Harbor Line

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Reviewed 16 March 2014

Enjoyed the sunset cruise on this really lovely boat. Great crew and captain. I enjoyed "steering the ship" and would recommend this sail to anyone except those with young children.

Thank thunderml
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
CHL745, Manager at Classic Harbor Line, responded to this reviewResponded 17 March 2014

Hello,
Steering the ship is always a wonderful experience to have aboard this vessel. To feel the wind power the ship is pretty breath taking.
Thank you for coming out and sharing your experience! We hope to have you out with us again in the future.

Classic Harbor Line

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Reviewed 15 March 2014

Had a windy night, on Friday, so we were really sailing. Crew was great, friendly and fast.
at delivering the complimentary drinks. My wife wanted a Ginger ale to go with her wine, and it came right up. We enjoyed the cheese and crackers,and also the shrimp as appetizers. I sat near Captain Ron, and when he was not busy getting the schooner up to top speed, or executing a turnabout , was very knowledgeable of the local waters and other smaller schooners in the harbor. Kind of left them in our wake.
As the sun set, It did get cool, and windy, but the crew brought out blankets for the few less naturally insulated, like my wife.
You know the first impression started with the enthusiastic young lady who sold us the tickets, made our reservations, was up to date on weather conditions, and answered all our our questions.
The sunset was awesome.

1  Thank Pining4keywest
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 15 March 2014

Gorgeous...fast schooner.... A wonderful wind and the boat moves faster than anything else with sails! Scenery can't be matched as the sun drops below the horizon.... Cracker and cheese,shrimp and beer and wine... Combine with a awesome captain and crew... Can't get enough sailing!

Thank Tim W
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
CHL745, Manager at Classic Harbor Line, responded to this reviewResponded 17 March 2014

Hello,

Thank you for coming out with us and thank you for sharing your experience. There really isnt anything more stunning than a sunset down in Key West aboard a sailing vessel.
We hope to have you out wtih us again in the future. Please make sure to check out our other locations as well.

Classic Harbor Line

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This response is the subjective opinion of the management representative and not of TripAdvisor LLC

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