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

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.

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.

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!

If you're really into history, US presidents, or just want to check out a house that is impeccably…read morepreserved from its era, I highly recommend visiting the Harry S. Truman Little White House in Key West. We opted for the White Glove VIP Tour, and it was hands-down awesome. The VIP package takes the standard visit to a whole new level. We were able to access exclusive areas that regular tour groups couldn't, got to sit inside the actual presidential limo, and went next door to examine rare historic artifacts in the museum foundation's private archives. The entire two-hour tour flew by, largely thanks to our guide, Greg, who was incredibly knowledgeable, engaging, and top-tier. Now, a word of caution for future visitors... Beware the Hawaiian Shirt Curse. Legend has it that during Truman's post-presidential travels in the Pacific, a local Hawaiian elder bestowed a vibrant, hand-stitched shirt upon him--along with a subtle tiki curse. The spell was woven directly into the fabric: anyone who dons the garment shall be consumed by an insatiable, endless drive to acquire tropical resort wear. During the VIP tour, I was actually permitted to try on one of Truman's original vintage Hawaiian shirts. Ever since that moment, I've been on a full-blown spending spree buying Hawaiian shirts. My closet is overflowing, my bank account is weeping, but my tropical wardrobe has never looked better. Whether the legend is real or I'm just rationalizing my new fashion obsession, this tour was easily one of the highlights of our trip. Don't skip the VIP upgrade!

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!