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Classic Harbor Line Key West

5.0

About this business

Classic Harbor Line: Key West 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 vessel 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 t... read more

Location details

202 William St, Key West, FL, 33040, United States

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WeekdayScheduleStatus
Mon9:00 a.m. to 9:00 p.m.
Tue9:00 a.m. to 9:00 p.m.
Wed9:00 a.m. to 9:00 p.m.
Thu9:00 a.m. to 9:00 p.m.
Fri9:00 a.m. to 9:00 p.m.
Sat9:00 a.m. to 9:00 p.m.
Sun9:00 a.m. to 9:00 p.m.
5.0655 reviews
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Johnna Rae's profile image
Johnna Rae 
recommend  Recommended
4 months ago

We went out last night (3/7/25) for the first ever Haunted Seas: Nautical Superstitions & Key West Ghost Stories cruise aboard Schooner America 2.0. The storytelling by Dan from Ghost Key West was phenomenal! It was super cool to be out on the water at night with only the light from the moon and the stars. We were lucky enough to see a shooting star and had a visit from some playful dolphins! Captain Rae, "Pirate Brad," Victoria, Chelsea, Dan, and Heather were awesome! I am looking forward to the next ghost cruise! 

Charles Piazza's profile image
Charles Piazza 
recommend  Recommended
4 months ago

America 2.0 is Wonderful Yachting Time Machine racing back to 1851. Captain Rae (Penn State Grad) and crew Brad, Lexi & Victoria we’re quite welcoming. Plus Capt Rae SHARED the HELM! 

Jay Moeller's profile image
Jay Moeller 
recommend  Recommended
4 months ago

This was a fantastic trip! Crew was superior and friendly! Wanted to make it the best experience! Enjoyed helping raise the sails and the team worked together to make it a fantastic sunset trip! 

Kyle Boss's profile image
Kyle Boss 
recommend  Recommended
5 months ago

Excellent Experience. The crew was great, the views were great, the drinks were great. We didn't realize there was going to be hors d'oeuvres as well, which was a fun surprise. We got lucky and saw a pod of dolphins while we were out. Highly recommended. 

Diane Smith's profile image
Diane Smith 
recommend  Recommended
5 months ago

What a great champagne sunset cruise! The appetizers were delicious and the crew was fantastic! Highly recommend this activity when you’re in Key West. 

Kelsey Houston's profile image
Kelsey Houston 
recommend  Recommended
6 months ago

Absolutely wonderful. Staff was very attentive and always around if you needed them. Would 100% do again in a heartbeat. Only thing stopping us is leaving. 

Beth W. Mays's profile image
Beth W. Mays 
recommend  Recommended
6 months ago

We were in town for a while and decided to make their Cocoa and Carols Cruise one of our excursions. It was a wonderful experience even though it was a foggy misty night. The crew was amazing and the Captain did a great job. Everyone was friendly and went above and beyond to make sure everyone was comfortable and enjoying themselves. Definitely recommend sailing with them! 

Cristina Lynne's profile image
Cristina Lynne 
recommend  Recommended
6 months ago

We took the Cocoa and Carols family friendly cruise and it was so fun. Every age loved it! The music was so fun, the cruise was gorgeous, the crew was fantastic and the Cocoa (mine was spiked) was yummy, 💯 recommend!!! 

William Harrison's profile image
William Harrison 
recommend  Recommended
7 months ago

Amazing experience with the America 2.0 crew! My wife and I have done a LOT of tall ship / schooner cruises and this was one of, if not THE best that we’ve been on. We went for a day sail on thanksgiving, it was perfect. Going to make this a tradition every year. Janet and her crew (Victoria, Dan, and Brad) were so so nice and knowledgeable, and just fun to sail with. 

Frequently asked questions about Classic Harbor Line Key West

How is Classic Harbor Line Key West rated?

Classic Harbor Line Key West has a 5 star rating with 655 reviews. 

When is Classic Harbor Line Key West open?

Classic Harbor Line Key West is closed now. It will open tomorrow at 9:00 a.m.