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 had tickets for the 07.18.26 trolleys. For $50 per person, it was definitely not worth it for…read moreus. It might be a solid tour of Key West, but we were wanting to get the tour while using the hop on and off part of it. We waited approx 15 minutes for a trolley at stop 11. There were 2 trolleys. I wondered why they weren't spaced out apart. But ok. We took it to stop 1 and did some touring and shopping. When we were ready to go, there are several trolleys at the stop, but no drivers. We waited a good 20 minutes before we left. They explained that they're only doing trolleys every 30 minutes now that the cruise ship had left port instead of 15 minutes. With how many trolleys we're going, why wasn't there a trolley leaving every 5 or 10 minutes? So then we got off at stop 5 to see what we wanted to see. By the time we were done, there were no more trolleys. UPDATING THIS REVIEW TO 3 stars. Because of the comment from the business, I did request a refund and I did receive it today. Thank you. ** Updated review to 3 stars. Per the business comment, I did put in for a refund. I did receive it today. I appreciate that. Thank you. ** I was very dissatisfied. Fix the timing. I have used 1 other system like this in Boston and it worked great! Trolleys coming and going all the time. I will not use this again in Key West or anywhere else this company is operating. Again, probably great if you're just going to do the tour. If you're going to use the hop on and off, start right when they start operating. I'm giving 2 stars because the tour people e has seemed to be knowledgeable.

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!

During the Sloan's Key West Ghost Hunt in the city, we learned about Robert the Doll who was…read morebrought to the island as a gift to some kid and that kid basically was mesmerized by said doll. Who knew dolls could be so big? Anywho, it was interesting enough for us to visit said doll and sign up for the 2nd tour bearing the Sloan name. This one was conducted at East Martello Museum, an old Civil War fort which surprisingly dates back to the 1860's. Our tour was conducted by local author David Sloan. He literally wrote the book on Robert the Doll, which you can buy on this tour and around the city. He also wrote other Key West ghostly tales like Haunted Key West, Ghosts of Key West and The Key West Key Lime Pie Cookbook ("limes have to die for this delicious pie" may or may not be words used in that book). David is a masterfully engaging storyteller who explains the history of Robert as well as the ol' Civil War Fort known now as the East Martello Museum, which sits at the entrance to the Key West Airport. Equipped with one Dowsing Rod and an EMF Reader that lights up when spirit energy is nearby, we wandered around the fort, into dark hallways, trying to bring out some spirits. People occasionally got hits (red and orange) but mine stayed green so spirits must be avoiding me like the gals did in high-school. The tour ends with everyone sitting around a glass case containing Robert the Doll. He's the main attraction. Great storytelling by David as some sounds are heard on the thingy that plays sounds (I forget the name). There were tales of people taking pictures of the doll or disrespecting the doll having horrible things happen to them. It was believable enough for us NOT to take pictures or whip it out and taunt the doll. I did take a picture of the poster of Robert the Doll though. The only thing bad that happened was my Windows PC rebooted on me without asking! Ugh! There's an extra add-on to stay afterwards to explore the fort on your own. We did not participate, but a few on our tour did. I haven't heard from them since! Should you go? Yes! It was interesting and informative and captivating. You can tell David has a passion for telling this tale and the stories of the fort and all things spooky. He's as Key West as a chicken crossing the road.

The guy that did our tour was amazing! So much fun, looking forward to going back again! Enjoyed…read morehearing all about Robert the Doll and seeing him!

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.

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

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.

great crew, food and total experience! Great snorkeling and educational tour of the fortread more

We recently took the Yankee Freedom Ferry to Dry Tortugas (8/3/26) and I absolutely loved this…read moreexperience, will 100% be coming back! My sister is on a mission to visit all of the U.S. National Parks, so Dry Tortugas was originally more of a bucket-list stop for her than for me. I honestly didn't expect to love it nearly as much as I did, but it ended up being one of my favorite parts of our trip. By the time we left, I was already thinking about coming back to camp and spend even more time snorkeling! The Yankee Freedom crew made the entire day incredibly easy and enjoyable. From the beginning, they went into so much detail about what to expect. I really appreciated how organized everything was, especially since it's basically an entire day excursion. Breakfast was available on the way out, lunch was provided shortly after we arrived, and snorkeling equipment was included. The bar opening on the ride back to Key West was also a fun way to end the day! After checking out the fort, we had time to explore and snorkel, which was easily one of my favorite parts of the day. The water and scenery were absolutely beautiful. What really stood out to me, though, was the crew. Everyone was so friendly, attentive, and genuinely fun to talk to, especially Matt. We appreciated his recommendations for bars to check out on Duval Street. We actually went to some of the places he recommended later, and they completely lived up to the hype, I had such a great time! He also saved my feet when I apparently decided shoes were optional on a scorching hot wooden dock and started splashing water on my feet for me . It was such a small gesture, but it really summed up how attentive and personable the crew was. I also really appreciated our tour guide, Ali, for answering all my questions. She was so sweet! Thom kept us entertained at the bar on the way home while making my first Rum Runner. Everyone brought something different to the experience, and those little interactions with the crew are honestly a big part of why the day was so memorable. It made the experience feel much more personal than I expected from such a busy excursion. My only "complaint" is that I wish I could have stayed longer! I felt like I could have spent hours more snorkeling and exploring. I went into this trip because visiting the national parks is something my sister loves, and somehow I left already planning my own return trip. Next time, I'd love to camp overnight so I can really take my time exploring and get even more snorkeling in. Between Dry Tortugas itself and the Yankee Freedom crew, this was easily one of the highlights of our Key West trip. If you're debating whether it's worth dedicating an entire day to it, do it. I can't wait to come back!

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.

From 1946 through 1952, President Harry Truman used this house as his winter vacation home, and…read morebecause he spent 175 days of his presidency here, it became known as the Little White House. Originally built by the U.S. Navy in 1890, the Little White House served as naval command headquarters during the Spanish-American War, and also played roles in both World Wars and the Cold War. Since Truman's days, many other presidents have also vacationed here, including Jimmy Carter and Bill Clinton. Today, the Little White House has been restored and turned into a museum. Also, don't forget to check the famous limousine while you are there. The only way to see inside the Truman Little White House in Key West is via a guided tour. But there is a small section near the gift shop that is free for visitors.

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!