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About Classic Harbor Line
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.
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Tours and Tickets by Classic Harbor Line

Key West Sunset Sail Aboard Schooner

See the sights of Key West during a relaxing sunset cruise aboard a sailboat that’s a replica of an antique schooner. Indulge in the all-included hors d'oeuvres and beer, wine, and Champagne as you take in the views and sail by local landmarks. Sit back, relax, and enjoy the sunset as your expert captain and sailing crew takes control of the sails. 
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2 hours
from $103.20
from $60.20
1481Reviews4Q&A
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IslandGirl wrote a review May 2021
Jacksonville, Florida3 contributions
I have done this trip before but this time took my 15 y/o grandson. It was awesome. He got to participate in raising the sails and steering the boat. What an awesome educational experience for him. We were able to get the last sunset cruise before they left for NY. Food and drinks were great, staff were awesome and so polite. Will definitely do again next year!
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Date of experience: May 2021
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Leslie E wrote a review May 2021
5 contributions1 helpful vote
Great experience! The crew engaged with the passengers. Plenty of photo opportunities with steering the ship, opportunities to help raise the sails etc. Pretty good food, plenty of beverages (alcohol and non). Plenty of room to move around, not too crowded, social distancing allowed for. Nice experience and sunset! Recommended!
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Date of experience: May 2021
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Stephen H wrote a review May 2021
Baltimore, Maryland128 contributions70 helpful votes
Great choice for a sunset cruise. I saw the sleek lines of the ship from Mallory Square a couple nights before and checked reviews the next day and booked. Really happy with our choice. This was the first time I had done a sunset cruise in Key West despite at least a dozen trips in my lifetime and I was definitely missing out. The crew was great, sail was smooth, and the snacks and drinks enjoyable. #1 the beer and other booze was ice cold as it's supposed to be. booking through tripadvisor didn't incur any of the additional fees others were charging or you can just go by the desk at their dock as well. They had set seating assignments based on requests and party size before hand so no need to line up ahead of time after check in. The crew really understood customer service which seems to be so rare these days so I would happily recommend them and we will sail with them again.
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Date of experience: May 2021
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Darlene Cypert wrote a review May 2021
2 contributions
We sailed on the day sail on May 18th with Captain Heather. The wind was just enough to keep us moving through the gorgeous water. The sun was warm and it was a great sailing day. We are so glad we were able to sail on the America 2.0! Classic Harbor has the nicest, professional staff from the ticket guys to the onboard crew. Nick and Janet made sure all of us were taken care of and they never lost their smiles! Captain Heather was informative and answered the many questions people asked with the knowledge and love she has for sailing. Thank you so much!
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Date of experience: May 2021
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Fun wrote a review May 2021
7 contributions
From researching their website, to booking and check-in, to sailing, this was one of the best harbor trips I've ever been on! Captain Ron was a very friendly informative guide. Stephanie hosted us all so wonderfully with her crew! Always checking to see if we needed anything. They loved answering questions. Learned so much about the island history. The ticket guide even asked how the tour was as I passed him. Recommend this to all!!
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Date of experience: May 2021
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