Top Key West Walking Tours

AJ was AMAZING! He went above and beyond - and made sure that there were restroom spots along the way. He was extremely knowledgeable - and made the history even more entertaining with providing historical images along the way with his iPad. He also found a way for our family to get great group photos. This tour over delivered!

Our Key West Historic Old Town Food Tour with 5 Authentic Tastings was absolutely fantastic, and Kennarose was a huge part of what made it so memorable. Kenna is everything you hope for in a tour guide—warm, funny, knowledgeable, engaging, and genuinely passionate about Key West. What really stood out, though, was how deeply connected she is to the local community. She doesn’t just know the history or memorize a script; she knows the people, the restaurants, the neighborhoods, and all the little details that make Key West feel like a real community rather than just a tourist destination. That gave the entire tour a much more personal and authentic feel. Every recommendation she made was spot on. We found ourselves mentally taking notes about places we wanted to return to, things we wanted to try, and spots we never would have known about on our own. She was also wonderful about answering questions and giving us suggestions beyond the tour itself, and you could tell that her recommendations came from genuine experience rather than a generic list of tourist favorites. The food was delicious, the pacing was great, and we learned a lot along the way—but Kennarose truly elevated the experience. She has that rare ability to make a group of strangers feel like they’re being shown around town by a very knowledgeable local friend. If you book the Key West Historic Old Town Food Tour with 5 Authentic Tastings and get Kennarose as your guide, you hit the jackpot. We would recommend both the tour and Kenna without hesitation. She was absolutely amazing!

Our guide was fantastic! He kept us together and didn’t start the story until everyone was gathered together. I was very impressed with his knowledge of haunted Key West and especially enjoyed his recommendations for places to eat and drink. We went to one of the places the next day and it was beyond expectations! My only negative comment is that some of the stories were also told on the hop on hop off trolley tour. He went farther in depth and was fabulous in his presentation. The commemorative t-shirt is a great touch.

This tour is totally worth the money. Received a shirt and got a free drink at all 5 stops. Learned a bit about KW history and our guide Sara was absolutely awesome! I'd recommend carrying cash to tip for your free drinks and to take care of your guide.

The two ladies that hosted our tour were as entertaining as they were informative. We experienced several establishments that I had never visited before. The cocktails were delicious and refreshing. Even better though were the presentations they gave at each location. It was a wonderful afternoon. I hope to take the tour again when I return.

It was a wonderful tour. The tour guide Dawn ( I think that was her name) was truly wonderful, knowledgable and engaging. We took the tour with 2 kids (8 and 10 y.o.) and some of the content was a bit scary but Dawn made sure it was perfect for all ages adjusting her language and making sure everyone was comfortable. Highly recommend.

Caleb was very knowledgeable about Hemingway and Old Town. He also shared a lot of information about Jimmy Buffet as an added bonus! For future tours, it would be great to know an ending point, as we had left our bikes all the way back at the Hemingway House.

AJ was knowledgeable about the early Cuban and Bahaman cultures that contributed to the historic neighborhoods. He provided historic photos on a laptop computer as we walked. His knowledge of architecture helped understand the community growth. We do recommend this as a cultural experience.