By far, the BEST guided tour I've ever been on! Richard, a 4th generation Key West resident,…read moreguided our Historic Homes & History of Key West Walking Tour. Richard gave us SO much information in 90 minutes of easy walking. To this day, my sister and I still talk about all the nuggets of history that he mentioned. Book ASAP and take lots of pictures!

We just went on the absolute best walking tour that we could have asked for! Richard was friendly,…read morereally knowledgeable, and tailored our tour to our interests. We will be visiting again for sure!

So I normally write long and detailed reviews, but this one will just be a quick one so I can…read morereview my recent 2026 vacation while the memories are still fresh! I bought my ticket for the Old Town Trolley Tours Key West as part of the Norwegian cruise line excursions list and therefore, paid more than I would have normally for something like this. I have been to Key West a few times before and had seen many of the important sites on the island on my own but my friends were doing this trolley tour so I did as well. And I still learned a lot! Manny, our tour guide, was born and raised on Key West and therefore, had a great perspective on everything. I think he is the reason why I recommend this tour. Like many others have said, the trolley itself isn't too comfortable but it is sturdy, and you can get on and off as much as you want. As we were on a moving vehicle, I didn't get the best pictures so you probably won't either. Look up the trolley schedule and plan your get on/get off stops well. And try to get a local tour guide if you can!

We like to use the Old Town Trolley to check out new locations. Always find them to be a good way…read moreto get a lay of the land. The drivers and staff were all helpful and friendly. Each of the drivers has a different style and sense of humor.

It's definitely a must visit when you're in Key West. Luscious greeneries all over the property…read more Keep an eye on the six-toe cats all around. Some of them occupy the cat house that looks like the Hemingway house itself. Very cute. The gift shop is at the back. You can find some cats there too. Very friendly and helpful staff

Heard this was a must stop in key west so had to come by…read more We didn't do the tour which I regret. I think the tour would have brought the whole thing together better. It was super crowded when we went which made it a bit hard to take everything in but loved the cute cats!

Amy was AMAZING, I am a Key West Local and have done a lot…read moretours here. I won this Island Ghost Tour at an Auction and really wasn't sure what to expect. We (a group of local friends) decided to go and had the best time. Amy's knowledge of the Island is above anyone I have met and her personality keeps you engaged, smiling, and want to know more. I highly recommend this tour.

Just do it. One of the best tale tellers I've ever seen! Talk about Entertainment and knowledge!…read moreShe's the best!

I am surprised that I am the first review this walking tour…read more The tour starts in Mallory Square in front of the ship wreck museum and is well organized. It is about and hour and one half guided walking tour and began at 9:30 in the morning. Our tour guide was really great. She took us around old city and thoroughly explained the history of Key West over the years. She also pointed out other places that she thought we might like to explore further such as the Truman Little White House. My family and myself really enjoyed the tour and it was a great way to explore old town Key West.

From the owner: Discover the beauty and captivating culture of the Conch Republic during a Historic Key Walking…read moreTour. This leisurely 1.4-mile stroll through a portion of the city's Old Town is highlighted by architectural gems, tropical plants and unique cultural sites and attractions as well as the nautical history that make the United States' southernmost city so unique.

When in Key West, make sure to check out the Conch Tour Train!…read more We booked this tour through the GoCity pass. By the end of the ride, I learned the history of the city, the booming times of the city until..., and some personal recommendations by our guide, Chris. He made the experience even better with his humor and in-depth knowledge. One of my favorite tidbits was the story behind the Conch Republic's tongue-in-cheek motto: "We seceded where others failed." In a playful protest, Key West once jokingly declared war on the United States and then immediately surrendered, turning the whole thing into a symbol of its independent spirit and humor. The train took us all around the island, passing by famous landmarks like President Truman's House, Ernest Hemingway's Home, Duval Street, and several museums. Overall, I'd highly recommend this tour for anyone looking for a fun, relaxing way to explore while staying cool in the Key West heat.

Convenient transportation option to maneuver around Key West. Cute quaint mode to get around and…read moreable to accommodate small groups.

I am a huge US National Parks fan and am trying to visit all of the US National Parks and Monuments…read moreduring my lifetime. Every time we visit Florida, I like to add another Park or Monument to my list. This time was Dry Tortugas National Park, a very unique park in that you have to book a ferry trip or board a sea plane in order to visit the park. We selected the less expensive option, the ferry, which is operated by Yankee Freedom. They offer a one day trip to Dry Tortugas for $250.00, which includes a breakfast, lunch, a guided tour of the fort, and the ferry ride to and from the island, which is 75 miles from Key West, in the Gulf of Mexico. The trip runs from 7 am - 5:30 pm. They also offer 10 spots per day for people who want to camp at Dry Tortugas. We were told that those camping spots fill up very fast. The parking for the day is in a nearby parking garage. It's pricey, so if you can get a ride there and back, that would be a less expensive option. The waiting area for the ferry is at the Yankee Freedom office. You have to show your ID in order to check in. They gave us each a number, which correlates to your number in the boarding process. The earlier you get there, the better. We were there a little after 7 am, and the waiting area was already packed. Channing, the guide, went over the boarding process and the day's itinerary. There were waivers to fill out for those borrowing snorkeling equipment. We boarded the boat and were able to find a couple of seats inside the boat. Immediately upon boarding, they had bagels and cream cheese available. Shortly after the ferry left, they opened the coffee/tea line, where you could also get a yogurt, fruit cocktail package, cereal, or oatmeal. We decided to opt into the guided tour of the fort. Channing was the tour guide. She was very excited to share the history of the fort with us and was extremely knowledgeable. I highly recommend the one hour tour of the fort. We learned so much from Channing! After the tour, we went back to the boat to eat lunch. They had Jersey Mike's sandwiches, chips, cookies, carrot and celery sticks, and beverages available. We ate on the boat and then spent the rest of the allotted time exploring the fort on our own. On the way back to Key West, they had a raffle, where you could buy raffle tickets to win merchandise, as well as a comment card raffle, where you could win another trip to Dry Tortugas by filling out the comment card. I won the comment card raffle! We have a year to use the coupon, and we will definitely be back! I'd like to do some snorkeling next time. We were so lucky to have calm seas during our trip. Be sure to bring Dramamine! We took some, just in case.

Our ride to and back from Dry Tortugas was an adventure! The excellent staff warned us in the…read moremorning that the waters were " sporty". They sold Dramamine for one dollar. It was well worth it. The boat ride out was fine for us. The staff handed out bags and ginger ale as several people got seasick. The way back was very sporty. But again the staff did an excellent job of taking care of all the passengers.

We came down to Key West for the week and hadn't originally planned to visit the museum. However,…read moreseveral friends recommended it, so we decided to go. I'm glad we did. The most striking thing, and something others have noted, is how low key everything feels. The structure, furnishings, and grounds are modest and very much middle class in character. Compared to how government operates today, the accommodations felt surprisingly austere. The exhibits and tour provide a fairly balanced view of Truman's presidency during that time. He seemed to have a more relaxed approach to the executive branch, often trading formal suits and ties for khakis and Hawaiian shirts. There are also reprints of newspaper clippings and political cartoons that don't always portray him or his administration in a positive light. To me, that made the experience feel more authentic, especially compared to the highly polished and carefully branded narratives often associated with modern political figures. Definitely worth the visit.

It's a cool spot if you're into American history, especially presidential…read more The house is beautiful and the grounds well kept. There is a presidential car also on site. Many placards, images and memorabilia to read, see and learn.

The best tour we have had of the Key West!! We learned so much about Key West on the tour and…read morescoped out many things to do and see thanks to our fantastic tour guide, Jordan! We only did the land tour, but it was well worth it. Loved Jordan's Jimmy Buffett knowledge as well. They have a fantastic team running the tours. Garfield was kind to pick us up from our breakfast and take us to the beginning of our tour. He was so fun and made us feel extremely welcome! Really felt like we got to know each other. At the end of our tour, Jordan even dropped us back off at our hotel. They made it so easy and treated us like family!

We were captained by Rebekah and Carrie was our first mate. They were amazing, very capable…read morenavigating choppy waters and answering our questions. We didn't get to see any dolphins, but the snorkel spot was really really fun. Carrie was really fun to talk to - it's always good to come across another Hoosier in the wild! I'd happily book another excursion with them!

I love history, especially where I'm visiting and I got a private tour from this lovely lady and…read moreI'm so sorry. I forgot her name. Brown shoulder length hair. Lots of information about the history of Key West and the curry family. Worth it. She also recommended a great breakfast place called Sunny eggs and it was superb!

The Martin Helling's House was beautiful. It was nice to get out of the sun and take a look inside.read more