We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Support this operator:Times are tough for the travel community right now. To show your support, consider leaving a review or posting photos of tours and experiences you have taken. Your support will go a long way in helping tour operators worldwide get back on their feet down the road

Classic Harbor Line

Key West, FL, USA
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.
Closed Now
Hours Today: 7:00 AM - 12:00 AM
See all hours
Certificate of Excellence
Travelers talk about
Tours and Tickets by Classic Harbor Line
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. 
Traveler rating
  • 1,317
  • 76
  • 7
  • 1
  • 7
Traveler type
Time of year
  • More
Selected filters
  • Filter
  • English
Popular mentions
Arstrazz wrote a review Jul 4
Tampa, Florida103 contributions29 helpful votes
Captian Amber and crew were awesome! We booked this sail because we are sailors ourselves and were interested in this beautiful boat (we just happened to walk by). It is an amazing ship inspired by an older design. We liked the fact that the ship would actually sail on wind
Read more
Date of experience: June 2020
Marty C wrote a review Jun 2020
Clemmons, North Carolina110 contributions6 helpful votes
Would highly recommend this adventure the captain and crew were amazing and very friendly and knowledgeable! My wife and I loved this ship and would definitely do again.The sunset is beautiful!
Read more
Date of experience: June 2020
Justin E wrote a review Jun 2020
Indianapolis, Indiana8 contributions
We got engaged on the trip and it was perfect. Captain Amber was great and her crew took really good care of us! Lots of champagne!
Read more
Date of experience: June 2020
Jeff S wrote a review Mar 2020
1 contribution
This excursion was a delight from beginning to end. The boat is beautiful, and it's an impressive sight to watch the crew raise the sails. Crew members were friendly and did their best to make sure that we had a pleasant experience. Only wish would be that the ride was longer!
Read more
Date of experience: March 2020
Katherine G wrote a review Mar 2020
The Villages, Florida358 contributions103 helpful votes
My husband and I were on a cruise ship docked for a day strolling down the wharf and commented that this would be a great day trip. Serendipity was on our side; sailing was leaving in 15 minutes. After a safety review we were off on a glorious day for a few hours. Who knew
Read more
Date of experience: February 2020