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Classic Harbor Line

#3 of 283 Tours in Key West
Certificate of Excellence
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Address: 202 William St, Key West, FL 33040-6645
Phone Number:
+1 305-293-7245
07:00 - 00:00
Open now
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Sun - Sat 07:00 - 00:00

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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Key West Sunset Sail Aboard Schooner America 2.0
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Classic Day Sail Aboard America 2.0

TripAdvisor Reviewer Highlights

Read all 1,011 reviews
Visitor rating
  • 929
  • 62
    Very good
  • 4
  • 1
  • 3
Great cruise!

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... read more

Reviewed 22 April 2016
via mobile
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1,011 Reviews from our TripAdvisor Community

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Showing 999: English reviews
Level Contributor
9 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 5 helpful votes
Reviewed 22 April 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
Reviewed 20 April 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
139 reviews
27 attraction reviews
common_n_attraction_reviews_1bd8 79 helpful votes
Reviewed 19 April 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
Reviewed 17 April 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
26 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 19 helpful votes
Reviewed 15 April 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
111 reviews
7 attraction reviews
common_n_attraction_reviews_1bd8 36 helpful votes
Reviewed 14 April 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
Reviewed 14 April 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
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
Reviewed 11 April 2016 via mobile

Couldn't have asked for a better evening. Weather was wonderful, captain Andrew and his female crew were amazing. We were one of the last ships to leave the harbor, but the first with sails up and sailing was perfect. The girls served beer and wine (along with soft drinks), as much as you wanted. And came around with veggies and... More 

1 Thank Robin E
Hollywood, Florida
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 5 helpful votes
Reviewed 10 April 2016

We had a wonderful time! The ship is gorgeous and the crew was really great.We got really lucky because the weather was absolutely perfect and the sunset was perfect. We drove down and stayed the night just for this sunset sail because last time we were in town for new years they were sold out.

1 Thank Chefapple27
Level Contributor
17 reviews
8 attraction reviews
common_n_attraction_reviews_1bd8 4 helpful votes
Reviewed 10 April 2016 via mobile

Absolutely wonderful sail. The crew did a wonderful and professional job, having raced sailing yachts offshore I really appreciated their expertize. Great landing by Heather!!

1 Thank Steven C

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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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