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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.
5.0611 reviews
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Kevin Serdynski's profile image
Kevin Serdynski 
recommend  Recommended
a week ago

Awesome experience! Sail was awesome, went out several miles and experienced sailing for the first time. Would highly recommend!! 

Business response:

Thank you, Kevin! We're honored that you chose us for your first sailing experience. We hope to welcome you aboard again in the future!  

Doug Travis's profile image
Doug Travis 
recommend  Recommended
2 weeks ago

Our sun set champaign cruise on America 2.0 was the highlight of our trip to Key West. The entire crew were amazing, they never stopped taking care of us while also doing all their duties. I highly recommend sailing with them, I will the next time I'm in Key West, you should too. 

Business response:

Hi Doug, thank you so much for this amazing review and for recommending our company. We look forward to sharing another sunset with you in the future!  

Kara Schultze's profile image
Kara Schultze 
recommend  Recommended
2 weeks ago

This was the most amazing excursion! The staff was amazing, very friendly, and helpful. The service was extraordinary and they did all this while also performing some hard labor getting those sails up. You won’t find a better crew and beautiful vessel to sail upon. The choice is up to you, but you’d be wrong to miss this opportunity if you’re in Key West. 

Business response:

Hi Kara! Thank you so much for this great review and for recommending us! We love to hear that you had a wonderful sailing experience with us and we greatly appreciate your compliments to our crew. We hope to welcome you aboard again in the future!  

Tracey L. Kelley's profile image
Tracey L. Kelley 
recommend  Recommended
a month ago

My husband and I enjoyed a wonderful sunset cruise with Classic Harbor Line in February, complete with interesting stories from the crew and tasty food and beverages. Beautiful way to pass the time and enjoy being out on the water. 

Business response:

We are glad you enjoyed your sail with us. February is a great time to visit Key West. Hope you'll join us again on your next trip. 

Johnna Rae's profile image
Johnna Rae 
recommend  Recommended
a month 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
a month 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
a month 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
2 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
2 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. 

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 611 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.