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.

“Must do in Key West!”

Classic Harbor Line
Book In Advance
More Info
and up
Classic Day Sail Aboard America 2.0
Ranked #4 of 284 Tours in Key West
Certificate of Excellence
More attraction details
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
Norwalk, Connecticut
2 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
“Must do in Key West!”
Reviewed April 22, 2010

I have enjoyed sunsets in many beautiful places, but the thing that made this one amazing was the crew and vessel. If you are looking for a "booze cruise", this is not for you. This is a class act, without being stuffy. The boat itself is gorgeous and fast. And the crew was warm, attentive, funny and extremely professional. We had a fantastic time and felt very much taken care of.

Thank smallworld41
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Write a Review

1,029 reviews from our community

Visitor rating
Date | Rating
  • Danish first
  • English first
  • French first
  • German first
  • Italian first
  • Portuguese first
  • Any
English first
Chandler, IN
Level Contributor
12 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 5 helpful votes
“Great way to spend a day”
Reviewed April 15, 2010

We have sailed the Adirondak II both times we visited Key West. The captain and crew know their way around the boat. The service and refreshments were very good. I even extended my visit to sail in the "Wreckers Race" on the last Sunday in March, great afternoon, followed by the "Star Cruise" that evening.

Thank whale344
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Dauphin Island, Alabama
2 reviews
“Adirondack II : An excellent sailing experience!”
Reviewed April 6, 2010

Captain Andrew, along with his crew, Chad & Mindy, Are wonderful hosts. The boat is outrageous fun, fast and comfortable. Easily one of Key West best vacation values!

Thank doryman76
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Newnan, GA
Level Contributor
139 reviews
28 attraction reviews
common_n_attraction_reviews_1bd8 37 helpful votes
“Key West Sunset Sail”
Reviewed April 6, 2010

Excellent trip. The boat is not filled to standing room only capacity like some boats we saw. The crew is quick to take care of any needs the passengers may have. We will do this again.

Thank DennisNewnan_GA
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Level Contributor
17 reviews
6 attraction reviews
common_n_attraction_reviews_1bd8 11 helpful votes
“Smooth, comfortable sailing”
Reviewed March 26, 2010

Went on the sunset cruise March 19, 2010. The crew was great on this beautiful boat. The captain wasted no time getting under sail - not motoring with sails up. Since it is a fast boat we went out further, came back and went back out again. Saw a turtle swim by which was cool. Seating was very comfortable. Served cheese and crackers and nice shrimp ring along with wine, champagne, beer and na drinks. Have been on Jolly Rover and the Sebago Cat which were also fun.

Thank creteman1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

Travelers who viewed Classic Harbor Line also viewed


Been to Classic Harbor Line? Share your experiences!

Write a Review Add Photos & Videos

Owners: What's your side of the story?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing