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!

Not Recommended -- Lack of Respect and Professionalism…read more I cannot recommend this tour company based on the way this tour operator treated people, particularly an older adult. Regardless of the situation, people working in the tourism industry should understand the importance of being courteous, patient, and respectful toward their guests. Unfortunately, that was not my experience. The tour operator was extremely rude and gave what I felt was a completely inappropriate and disrespectful response to a senior citizen. When he received a response in return, his behavior escalated. He became aggressive and appeared ready to get off the bus and confront the person physically. Thankfully, someone younger stepped in and advised him not to get off the bus before the situation could escalate further. What is most disappointing is that this entire situation could have been avoided with something as simple as, "No," or "No, ma'am." There was absolutely no reason for the interaction to become confrontational. Tourism is about hospitality, and respect should be extended to everyone--especially senior citizens. A tour operator represents not only themselves but the company and the destination they are serving. Based on this experience, I would not recommend this tour company.

You have to visit as it is one of the best and unique places to see in the area. The history and…read moreitems on display are amazing. Then, there are 60-very spoiled cats that live in and out the house. Not all have 6-toes, but they all carry the gene. Scott was our tour guide, and he was enthusiastic and engaging. He knew the cat's names, and told you which one not to pet. It was a hot day, which added to the smell of roaming cats. That was the only negative part of the tour for me. However, it was nice to see the 5-kittens outside of their enclosures getting enriched with toys with visitors. What a quality and unique experience.

If you're visiting Key West, the Hemingway House is practically a required stop, but your mileage…read moremay vary depending on what brings you here. We went during the off-season, so we didn't have to wait long for our tour to start or stand in any real line to get in. By the time we were leaving, though, we noticed a small line starting to form. Personally, I wouldn't wait more than five minutes to get inside unless you're a die-hard Hemingway scholar. The tour itself is totally fine, you get to walk through his small, modest home (which thankfully has air conditioning) and check out some historical memorabilia from his life and writing career. It's neat, but straightforward. Honestly, it seems like most people visiting are just cat people, and fair enough, the grounds are littered with six-toed cats, and they are indisputably the real star attraction of the property. On a side note: after our visit, Ernest Hemingway actually appeared to me in a dream. He made a direct request, asking if I could bring him some Krispy Kreme doughnuts because he is utterly exhausted from people bringing him Dunkin' Donuts. I told Papa I'd do what I could, but if there's a long line at the drive-thru, he's out of luck, I'm strictly not waiting in lines on this vacation.

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!

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.

Very fun way to get a tour of Key West and learn about the island! I've done it twice and learned…read moresomething new each time.

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.

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!

My daughter and I took this trip on 07.16.26. First visit to Key West…read more Check in was super smooth. Hollywood relayed the directions and expectations very clearly. The boat ride both ways were amazing! Crew was great. Hollywood, again, was great with directions for the ride. Hours for things were clearly posted. The Fort was great! I have seen other forts before, but this one was different. We signed up for the 20 minute talk once we were in the fort along with the 1 hour walk tour. Both were very insightful. We didn't make it very far in the fort on the tour, but Hollywood did a great job with the highlights. Great that breakfast & lunch were provided. Snorkeling gear was provided for everyone. We did not use, but many people enjoyed using it. They really did have enough for whoever wanted them. We did get burnt riding outside and being at the fort. I can't stress enough to apply sunscreen way more often than we did! My only negatives are these. The new Park Ranger came to listen to the 20 minute talk because, and she said this...' you know more than I do'. But this wasn't for the boat. The other was when we were in Dr Mudd's area. I know he was stressing to us how great the weather was (cooler than normal) and that we shouldn't be acting so hot. It felt almost like he broke from the script to scold us. I know he was trying to relate the conditions from back when the fort was in use vs us being there. I thought someone did something wrong and he needed to talk to us about it. I know some people were acting super hot. I know is a silly rant, but I don't like getting lumped in to something when I feel like we're in trouble. Anyway...highly recommend!

This was my favorite touristy tours we took while visiting Key West. I learned a lot about the area…read moreand President Truman. I was very impressed with the restored home and real lived in items as historic pieces on display. They still have more work to keep this museum going and protected, but it can be done. They also had a nice gift shop, with great tour guides. Bravo!

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!