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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
202 William St, Key West, FL, 33040, United States
Get directionsWeekday | Schedule | Status |
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Mon | 9:00 a.m. to 9:00 p.m. | |
Tue | 9:00 a.m. to 9:00 p.m. | |
Wed | 9:00 a.m. to 9:00 p.m. | |
Thu | 9:00 a.m. to 9:00 p.m. | |
Fri | 9:00 a.m. to 9:00 p.m. | |
Sat | 9:00 a.m. to 9:00 p.m. | |
Sun | 9:00 a.m. to 9:00 p.m. |
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!
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!
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!
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.
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.
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.
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!
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!!!
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.
Classic Harbor Line Key West has a 5 star rating with 655 reviews.
Classic Harbor Line Key West is closed now. It will open tomorrow at 9:00 a.m.