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Classic Harbor Line

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Address: 202 Williams Street, Key West, FL 33040
Phone Number: 305-293-7245
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7:00 am - 12:00 am
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Sun - Sat 7:00 am - 12:00 am

Classic Harbor Line, operating renowned day sail operations in Newport...

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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TripAdvisor Reviewer Highlights

Read all 428 reviews
Visitor rating
  • 397
  • 28
    Very good
  • 2
  • 1
  • 0
America 2.0

I have lived in Key West for over 16 years and have often gone with out-of-town guests on Sunset Sails. America 2.0 was, by far, the best Sunset experience. The crew was... read more

5 of 5 starsReviewed 2 days ago
Key West, Florida, United States

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428 Reviews from our TripAdvisor Community

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Date | Rating
  • Danish first
  • English first
  • French first
  • German first
  • Italian first
  • Any
English first
Key West, Florida, United States
Level Contributor
3 reviews
3 attraction reviews
5 of 5 stars Reviewed 2 days ago NEW

I have lived in Key West for over 16 years and have often gone with out-of-town guests on Sunset Sails. America 2.0 was, by far, the best Sunset experience. The crew was excellent, Captain Ron was extremely knowledgeable with excellent people skills. Safely was at the top of their attention. The price was very reasonable with wine, beer, champaign, sodas... More 

Thank SidinKeyWest
Rickmansworth, United Kingdom
Level Contributor
36 reviews
10 attraction reviews
common_n_attraction_reviews_1bd8 14 helpful votes
5 of 5 stars Reviewed 1 week ago

We had a wonderful sunset cruise on 11 Nov with Captain Ron and his crew; Sean, Heather and Melissa. A perfect evening. There were 16 of us plus the crew, which was great. Very peaceful once the sails were our only means of power. It was a great thrill to be able to be given the chance of steering this... More 

Thank John T
St. Joseph, MI
Level Contributor
47 reviews
10 attraction reviews
common_n_attraction_reviews_1bd8 9 helpful votes
4 of 5 stars Reviewed 1 week ago

Just got back from a sunset cruise on America 2.0. Delightful! Beautiful cruise, drinks are included as is snacks and personalities aboard are great. Highly recommend. Great thing to do before dinner.

Thank AmySt_Joseph_MI
Federal Way, Washington
Level Contributor
272 reviews
117 attraction reviews
common_n_attraction_reviews_1bd8 155 helpful votes
5 of 5 stars Reviewed September 26, 2015

We booked a 2PM cruise on this 2 masted schooner Adirondack III. They left on time and we slowly motored out of the mooring at Rowes wharf. As soon as we were clear of the docks, the crew of 3 set sail and we were under wind power until we returned to the docks. Our captain was knowledgable and told... More 

1 Thank fsdukejr
Galena, Illinois
Level Contributor
11 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed July 10, 2015

We were in a quandary as to which sunset cruise we should take. We knew we didn't want a "party-party" boat, but we still wanted to have fun. The crew we had was awesome, the food and drinks were perfect, and our captain outstanding. AND the BEST was the beautiful sunset. If you are in Key West...a sunset cruise with... More 

2 Thank WLB2752
New Cumberland, Pennsylvania, United States
Level Contributor
75 reviews
33 attraction reviews
common_n_attraction_reviews_1bd8 26 helpful votes
4 of 5 stars Reviewed May 25, 2015

My husband and I signed up for an afternoon sail cruise and it was fabulous. The weather was perfect. It was about 2-2 1/2 hours in length. Many different types of beverages were served. It was a very enjoyable time. Maybe next time we'll do a sunset cruise.

1 Thank Lori E
North Conway, New Hampshire
1 review
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed May 14, 2015

We have done the sunset cruise on the America II twice now and each time was perfect. We took our entire family, 13 of us, daughters, husbands, and 7 grandkids from 20yrs old down to 8 yrs old last year as the final night of a week long birthday celebration for my husband's 70th birthday. It was wonderful. The kids... More 

1 Thank Sharon W
Woking, United Kingdom
Level Contributor
5 reviews
common_n_attraction_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed May 5, 2015

After a very wet day in Key West (it actually flooded) we were surprised it actually sailed lots of people did not turn up and only four us actually boarded, we were treated to a great evenings sailing we all had a good chance of steering and the two lads helped hoist the sails. The crew cannot do enough for... More 

1 Thank Bob W
Hartford, Connecticut
1 review
common_n_attraction_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed May 1, 2015

We had a wonderful, relaxing sunset cruise on the schooner America 2.0. The cost of the trip included hors d'oeuvres and drinks and a chance to steer the boat. The crew was friendly and attentive. The cruise was everything we wanted.

3 Thank ctvacati0ner
Chicago, Illinois
Level Contributor
12 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed April 25, 2015

The trip on the schooner was relaxing and great to be able to enjoy the power of just the sales. We choose a good day to be out on it. The captain allowed passages to drive the boat while under sail power. The crew was very helpful

1 Thank Wes A

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