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Classic Harbor Line

#6 of 275 Tours in Key West
Certificate of Excellence
Sponsored by:
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Address: 202 William St, Key West, FL 33040-6645
Phone Number: 305-293-7245
7:00 am - 12:00 am
Open now
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Sun - Sat 7:00 am - 12:00 am

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

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 682 reviews
Visitor rating
  • 624
  • 42
    Very good
  • 4
  • 1
  • 1
Good value for the money!

Had a great time aboard the America 2. I believe that for the money I spent I got an excellent value. The ship was incredible. The crew was top notch and the quality of beer... read more

5 of 5 bubblesReviewed April 28, 2016
Ben M
Orlando, Florida, United States

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682 Reviews from our TripAdvisor Community

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Showing 672: English reviews
Orlando, Florida, United States
Level Contributor
5 reviews
common_n_attraction_reviews_1bd8 7 helpful votes
5 of 5 bubbles Reviewed April 28, 2016

Had a great time aboard the America 2. I believe that for the money I spent I got an excellent value. The ship was incredible. The crew was top notch and the quality of beer, wine, cheeses and shrimp was excellent. The cruise lasted two hours in a setting that is hard to beat. Truly glad we did this.

4 Thank Ben M
Holland, New York
Level Contributor
5 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 bubbles Reviewed April 27, 2016

Wonderful afternoon cruise. The Captain and 2 deck hands were fantastic and friendly. The girls were very friendly and helpful. Happy to chat with everyone and very attentive to all's needs. Enjoyed the trip and scenic views!!

1 Thank JaniceZ145
Rosenheim, Germany
Level Contributor
21 reviews
10 attraction reviews
common_n_attraction_reviews_1bd8 6 helpful votes
5 of 5 bubbles Reviewed April 24, 2016

love this 3 pole shooner, the peaceful sailing and the very attentive crew. Thanks for this great experience in the water in front of key west, the finger food, wine and beer. This is definitely a trip you will not forget. I highly recommend this instead doing a sunset trip on a party boat.

2 Thank angel7270
Level Contributor
9 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 5 helpful votes
5 of 5 bubbles Reviewed April 22, 2016 via mobile

Beautiful boat, excellent crew and captain. Very relaxed cruise with plenty of wine & beer and great snacks. Not crowded, plenty of room to move around. You can't go wrong with this cruise!

1 Thank Nupilot
woodbury nj
Level Contributor
4 reviews
common_n_attraction_reviews_1bd8 8 helpful votes
5 of 5 bubbles Reviewed April 20, 2016 via mobile

We went out Sunday night and it was a gorgeous night!!! This is the way to experience your Key West Sunset. We were really moving!!!The captain and crew were so much fun !!! We were on board with really fun people!!! Lot's to drink and really nice snacks!!! The all girl crew were very attentive!! Worth the money for sure!!!... More 

1 Thank joanflo
United Kingdom
Level Contributor
138 reviews
27 attraction reviews
common_n_attraction_reviews_1bd8 77 helpful votes
5 of 5 bubbles Reviewed April 19, 2016

We booked a Sunset trip on the America 2.0. One word: FANTASTIC. Welcoming & fun crew. Great sailing experience. I felt very safe in their hands. Drinks and snacks provided (and plentiful supply of both). Crew very engaging and answered questions. The sunset was awesome, we had great weather conditions for the sail. The America 2.0 is moving up to... More 

1 Thank Mr-Cinnamon-UK
Houston, Texas
1 review
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed April 17, 2016 via mobile

The boat is beautiful and the crew was great! We were a group of 13 people, and we couldn't have asked for a better evening. We were extremely happy we didn't go on any of the other sunset cruises we passed by. They were blasting music, and seemed to be way too crowded to be comfortable. We had a beautiful,... More 

1 Thank Martehk
Fredericksburg, Virginia
Level Contributor
21 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 17 helpful votes
4 of 5 bubbles Reviewed April 14, 2016

This was a wonderful cruise with a fantastic crew. If you don't want a loud party boat and you want to enjoy the sound of the sea and the beauty of the sunset, this is the boat for you. The only reason I didn't give it 5 stars was because the food was sparse. We were served 3 crackers each... More 

2 Thank Sherry S
Atlanta, Georgia
Level Contributor
103 reviews
6 attraction reviews
common_n_attraction_reviews_1bd8 34 helpful votes
5 of 5 bubbles Reviewed April 14, 2016

Went last week on a very windy day and had a fantastic ride with my new wife! Captain asked if we wanted to go out where the real wind was and everyone agreed! The waves were huge! We had a fantastic heel on! The two young ladies crewing were amazing. You never had to ask for a drink. As a... More 

1 Thank Joe M
Chesapeake Beach, Maryland, United States
Level Contributor
9 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 8 helpful votes
5 of 5 bubbles Reviewed April 13, 2016

Beautiful sunset cruise. Capt Andrew and his crew were great! Perfect weather and calm waters! Even had a couple renew their wedding vows!!! PERFECT!!

1 Thank Mikie G

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  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
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