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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.
5.0633 reviews
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Greer Nolan's profile image
Greer Nolan 
recommend  Recommended
a day ago

Had a beautiful sail May 10. Loved that we were under full sail all the way. Delicious treats and great service. 

Business response:

Thank you so much for your feedback! It is most rewarding to share the experience of sailing with you all. We hope to welcome you aboard in the future.  

Barbara Passaro Gromwaldt's profile image
Barbara Passaro Gromwaldt 
recommend  Recommended
3 days ago

Americana 2.0 Key West 5/2025: Very well done from start to finish! On time, organized, friendly, well run, professional, personable crew, very informative, literally everything was perfect! Thanks to the crew for having us aboard! 

Business response:

Thank you so much for your compliments! It was truly our pleasure to have you aboard and share our love for sailing and Key West with you.  

Julie Scruggs Locker's profile image
Julie Scruggs Locker 
recommend  Recommended
a week ago

The sunset cruise was an awesome experience. The crew was extremely friendly and attentive. The food and drinks were also very good. Gorgeous view of the sunset. Beautiful sail, I highly recommend it! thanks to the crew for making a great memory 

Business response:

Thank you so much for this glowing review, Julie! It was a pleasure to host you. Thank you for sharing a sunset with us and we hope to welcome you aboard again in the future! 

Kim Ritter Weisner's profile image
Kim Ritter Weisner 
recommend  Recommended
a week ago

The staff works hard to make sure everyone is taken care of and ensures a smooth ride. There was plenty of room and the food was great. Sunset can’t be beat either! 

Business response:

We appreciate your compliments to our wonderful crew! We are so glad you had an amazing sailing experience and we thank you got your recommendation of our company.  

Kevin Serdynski's profile image
Kevin Serdynski 
recommend  Recommended
a month 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
a month 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
a month 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
2 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 

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 633 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.