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“Just great - great boat, great crew, great fun.”

Classic Harbor Line
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Key West Sunset Sail Aboard Schooner America 2.0
Ranked #3 of 283 Tours in Key West
Certificate of Excellence
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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
Clarks Summit, Pennsylvania
Level Contributor
45 reviews
10 attraction reviews
common_n_attraction_reviews_1bd8 52 helpful votes
“Just great - great boat, great crew, great fun.”
Reviewed November 20, 2012

My friend and I wanted to go on a sailing cruise to see the Key West sunset. We wandered around the harbor and talked to a number of people about their boats. We stopped and discussed sunset cruises with the woman (I think her name was Beth) that was in the Classic Harbor Line booth. She was friendly, engaged, knowledgeable and fun and we were sold. The cruise was a delight - and it was not due to the shrimp and cheese plate. Sweeny was our captain and Margo and Scott were on as crew. I actually wrote down their names because I was so impressed and was having so much fun that I really wanted to share this experience. We helped to raise the sails, had a few glasses of vino (not a great label but no one cared). Scott was giving out Sweeny's leftover Halloween candy - Margo was chatting as she expertly hoisted sails and Sweeny was cracking jokes. We passed a ship where a couple was getting married - we clapped and yeehaaed. One historic sailboat "fired" on us and we booed and jeered. We all told stories and enjoyed the ride. I even steered for a bit. This was the most fun I had in Key West - and it was overcast so my good time wasn't due to viewing a spectacular sunset. Sweeny did say that if the sun didn't set we'd get our money back.

Visited November 2012
Thank pear3150
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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1,001 reviews from our community

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Cudjoe Key, Florida
Level Contributor
195 reviews
47 attraction reviews
common_n_attraction_reviews_1bd8 47 helpful votes
“A great sunset sail”
Reviewed November 19, 2012

There's a lot of choices in Key West, and we've done a few of them. Adirondack III is really good - the crew was extremely capable and very pleasant. They were engaging and very friendly. They are very attentive, the cheese & crackers, shrimp cocktail, champagne, wine, and beer was all very high quality. This is one you want to do - you'll remember it for a long time.

And good news - they guarantee the sun will set too :-)

Visited November 2012
1 Thank shark4rae
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
White River Junction, Vermont
Level Contributor
8 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
“Sunset Sail 11/15/2012”
Reviewed November 18, 2012

What a great night of sailing, first night on the Adirondack III and first time in Key West. Only 12 people on board and the crew was great and interacted with everyone on board. All offered the opportunity to help with raising the sails. Food and drinks were very good and offered thru out the trip. Love the cannons being fired at our boat from other ship passing by.

Visited November 2012
1 Thank VermontersWilder_vt
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Inver Grove Heights, Minnesota
Level Contributor
3 reviews
“Great Day at Sea”
Reviewed November 12, 2012

Myself and 6 of my quest did an afternoon sail on 11/10/2012, our first time on Adirondack III. We all had a great afternoon aboard. There were only about 11 people on the trip, so it wasn't crowded and the crew was great interacting with us all. We were offered the opportunity to help raise the sails and some in our party did. Captain Ron offered me the chance to get behind the wheel and I did, what a great opportunity. .Beautiful weather for sailing. Great value drinks, beers, wine, soft drinks, water. Highly recommended and we would certainly do it again. If time would have permitted we were considering going out on the sunset sail maybe next time. Thank you, Captain Ron and crew for a great day in Key West.

Visited November 2012
Thank Kenneth D
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
South San Francisco, California
Level Contributor
51 reviews
12 attraction reviews
common_n_attraction_reviews_1bd8 18 helpful votes
“Beautiful morning sail!”
Reviewed November 4, 2012

We throughly enjoyed our morning Mimosa sail. From the moment we checked in to the moment we left the ship we were treated in such a warm and friendly manner. Capt. Jeremy and his hard working crew of women were friendly helpful. We enjoyed the information about the area and the schooner. The Mimosa's were nice and refreshing and not at all skimpy on the Champagne. Don't miss this wonderful experience!

Visited October 2012
Thank Jackie B
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

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