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Classic Harbor Line

202 Williams Street, Key West, FL 33040
305-293-7245
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Ranked #9 of 291 activities in Key West
Certificate of Excellence 2013
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Type: Tours
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... more » 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. « less
Useful Information: Activities for older children
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380 reviews from our community

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Date | Rating
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English first
1 review
5 of 5 stars Reviewed April 3, 2014

Can't rate this highly enough plenty to drink both soft and alcoholic. Knowledgable crew. Fantastic sailing really filled the sails. Enjoyed everything about the evening.

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Tampa Florida
Senior Contributor
31 reviews 31 reviews
10 attraction reviews
50 helpful votes 50 helpful votes
5 of 5 stars Reviewed March 20, 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... More

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Mastic, NY
Contributor
19 reviews 19 reviews
15 helpful votes 15 helpful votes
5 of 5 stars Reviewed March 20, 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... More

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Montpelier, Vermont
Contributor
17 reviews 17 reviews
4 attraction reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed March 16, 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.

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CHL745, Manager at Classic Harbor Line, responded to this review

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 More

Londonderry, New Hampshire
2 reviews
5 of 5 stars Reviewed March 15, 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!

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CHL745, Manager at Classic Harbor Line, responded to this review

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 More

Wake Forest, North Carolina
Senior Reviewer
10 reviews 10 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed March 6, 2014

Had a GREAT evening sunset cruise aboard the Schooner America 2.0!! It was a great trip, great food, great company and a great skipper & crew! This is a must do on any trip to Key West!!

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CHL745, Manager at Classic Harbor Line, responded to this review

Hello! Thank you for coming out with us on your vacation in Key West and Thank you for sharing your experience! Sounds like you enjoyed and we hope to have you out with us again in Key West or in one of our other locations! Classic Harbor Line More

Orleans, Massachusetts
Top Contributor
65 reviews 65 reviews
9 attraction reviews
28 helpful votes 28 helpful votes
5 of 5 stars Reviewed March 2, 2014 via mobile

Well done sunset sail. This sunset sail was very well done, staff was excellent. Check the weather and enjoy the evening!

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CHL745, Manager at Classic Harbor Line, responded to this review

Hello, Thank you for joining us on a sunset sail in Key West, we hope you enjoyed your stay! We also hope to have you out with us again, if not in Key West, then in another location of ours! (We have a location in Boston!) Happy Sails! Classic Harbor Line More

Keswick, Virginia
Top Contributor
59 reviews 59 reviews
14 attraction reviews
25 helpful votes 25 helpful votes
5 of 5 stars Reviewed February 23, 2014

On a brisk breezy night when the ship's sides tilted nearly into the Gulf, our party of three joined an expert crew of three young women and the male captain for a sold-out fun sunset cruise. The crew and captain made everyone feel comfortable and the visitors were encouraged to help set the sails and steer the boat.

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Classic H, Manager at Classic Harbor Line, responded to this review

Hello, Sounds like quite the sailing experience! That is definitely something that Schooner America 2.0 will give you: An amazing sailing experience. Thank you for giving our crew a shout out! We will make sure to pass it along to them as they are excellent at what they do and are very hard working. We hope to have you out... More

detroit,mi
Senior Contributor
21 reviews 21 reviews
4 attraction reviews
10 helpful votes 10 helpful votes
5 of 5 stars Reviewed February 22, 2014 via mobile

I sent on a sail on the America2.0 The sail was perfect and the crew was helpful and very efficient in their job. I would recommend going out on this magnificent boat-a great way to spend a few hours.

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Classic H, Manager at Classic Harbor Line, responded to this review

Hello, Thank you very much for coming out with us. We appreciate your feedback and hope that you will join us again out on the high seas! Classic Harbor Line More

Alexandria, Virginia
Contributor
11 reviews 11 reviews
3 attraction reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed February 18, 2014

My husband and I sailed on the America 2.0 in Key West (Feb 13th) and had a fabulous time. The captain and crew could not have been more accommodating..Very professional crew to take us out on a blustery day -- sailing around Key West was amazing and hearing about the boat made it very personal. They sail twice a day... More

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Classic H, Manager at Classic Harbor Line, responded to this review

Hello, A sailor for a day!?? You mean you are now a sailor for life! You have fallen in love with the experience of being out there on the ocean with the wind and water and vessel all working together! It is a fascinating vessel with allot of history. We want to thank you for sharing your experience with us... More

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