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Classic Harbor Line Key West

4.9

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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.
4.9723 reviews
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Johnna Rae's profile image
Johnna Rae 
recommend  Recommended
7 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! 

Business response:

Thank you for sharing our very first Ghost sail on America 2.0, we are so excited to add this to our sailing options. The shooting star and dolphins were spectacular!! Thanks for the 5-star review and we hope to see you on next month's cruise 

Charles Piazza's profile image
Charles Piazza 
recommend  Recommended
8 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! 

Business response:

We're happy to hear you enjoyed your experience on America 2.0 with Captain Rae and the crew. Thank you for sharing your review! 

Jay Moeller's profile image
Jay Moeller 
recommend  Recommended
8 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! 

Business response:

We are so glad you enjoyed your sail and even participated in it! Providing our guests with the best experience possible is one of our top priorities. Thank you for your wonderful feedback and recognition of our crew.  

Kyle Boss's profile image
Kyle Boss 
recommend  Recommended
8 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. 

Business response:

Thank you for your review. We are thrilled to hear about your excellent experience with us. 

Diane Smith's profile image
Diane Smith 
recommend  Recommended
8 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
9 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. 

Business response:

Hi Kelsey, Thank you for booking a cruise with us and taking some time to leave a review. We are happy to hear that it was a great time and that the quality of the service added to your experience. We hope to have more opportunities to welcome you aboard in the future! Warmly, Classic Harbor Line Key West 

Beth W. Mays's profile image
Beth W. Mays 
recommend  Recommended
10 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! 

Business response:

Hi Beth, Thank you for booking our new cruise and taking some time to leave a review. We are happy to hear that it was a great time and that the quality of the service from the crew added to your experience. We appreciate the recommendation and hope to have more opportunities to welcome you aboard in the future! Warmly, Classic Harbor Line Key West 

Cristina Lynne's profile image
Cristina Lynne 
recommend  Recommended
10 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!!! 

Business response:

Hi Cristina, Thank you for booking our new cruise and taking some time to leave a review. We are happy to hear that it was a great time and that you enjoyed the music, the drinks, and the friendly service. We hope to have more opportunities to welcome you aboard in the future! Warmly, Classic Harbor Line Key West 

William Harrison's profile image
William Harrison 
recommend  Recommended
10 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 4.9 star rating with 723 reviews. 

When is Classic Harbor Line Key West open?

Classic Harbor Line Key West is open now. It will close at 9:00 p.m.