A tourist staple since 1958, offering open-air train tours throughout the town. This was one of my…read morefavorite paid attracts on my entire trip. Tickets were ~$40 and a little over an hour long tour, with a stop right in the middle for a bathroom break and souvenir shopping. It was a fun yet informative experience, offering bits of local history and stories about old Key West. In my opinion the perfect way to see everything this charming city has to offer.

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.

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.

What an AWESOME DAY!!! This was by far one of the best day's…read moreand experiences we've had in our favorite town, Key West!! From the ease of the booking and contact with Captain Morgan as to where to catch the boat to a beautiful day full of sites, fun and laughter. We (the four of us) have been in Key West on many trips and decided with the great weather doing an all day Tiki Boat/Sand Bar trip would be so much fun and it did not disappoint. The highlight of the trip was our Captain. Truly a great guy, friendly, welcoming, great sense of humor and very professional. Of course we gave him a hard time about being "Captain Morgan", which by the way he gets it a lot! We had the best time talking with him and as we all got to know each other we had blast giving each other fun stories and joking around. Morgan told us so much about the waters around the Keys. Took us to several very pretty spots in which we saw more wild life that day then he said he's seen in a while. We saw nurse shark, several dolphin pods and one with a little baby! Sting ray and some barracuda The waters are a beautiful blue like you seen no where else. Captain Morgan took us to see the beautiful mangroves, so many lizards in the trees it was crazy... and just gorgeous. We pulled up on a little beach to check out the views and hang in the water. We brought some drinks, sandwiches and snacks... Such a fun experience to relax on this boat. The tiki theme is so fun, clean boat and great music. Defiantly gives you the island vibe. Highly recommend asking for Captain Morgan, book this company and have a blast. We plan to do this again on our next visit. Great day - Thanks Morgan for making is so!

Okay.....how can you NOT have an awesome time on a "Tiki" boat with a captain whose name is…read more"Morgan?" I kid you not....CAPTAIN MORGAN! He's only been with the company for 4 months---but had all kinds of fun filed facts about Key West. The sun was behind clouds...and it POURED on our way back in....BUT none of that mattered as we had a great captain, fun music, libations :) and friends/family. I would recommend doing this fun, floating tiki party!!!! And try to get Capt Morgan....I am sure everyone would be great....but he's REALLY awesome. Thanks for helping us make forever memories!

Great history overview with lots of fun facts on this tour. We have been to Key West a few times…read moreand still felt like we learned a ton. James was our guide and he was amazing. It was blazing hot the day we went but James managed to find shady breezy spots along the way. And he brought lots of cold water. Highly recommend!

Salty was a fantastic tour guide! He led us throughout Key West on non busy roads, which made for…read morea very relaxing bike tour. He was extremely knowledgeable about the beautiful locations around Key West where we stopped. Highly recommend this tour w Salty!

**if you have a cat allergies SKIP THIS you will be miserable. All other people this is one of the…read morebest experiences on key west. Full stop When visiting Key West this is a MUST DO. The staff are all so friendly. they keep it infomral so it's not stuffly or rehersed. In our tour group there about 15 people. 4 of whuch were kids and our guide tailored it to them which both sweet and adorable. He also mentioned multiple times that if we wnated a different experance to stick aorund for the next tour. So from tour to tour you'll get a completely different experiace and infomation which is not typical and definatly a more interesting experiance (I do a lot of antique and historically signifaicnt home tours lol) The cats are amazon. Most are very used to people and are happy for some gental and respictful attention. Please if you are visiting, be respectful of the rules and don't pick htem up. If one jumps in your laslp thats fine but don't pick them up on your own. Pets and belly rubs and photos and ear scratches al welcome. We saw margarita glasses being used a water bowls an have implented this at our house now. I could have spent all day here and if we ever return to Key West we'll be back as I;m sure the experience will be different.

When we planned to come to Key West, this was the first item on my bucket list. And it did not…read moredisappoint. After paying to get in, we did a little tour on our own. Mostly my wife looking at the cats and trying to get their attention. We had a cat, they do whatever they want when they want to. At a given time, we came back to the front for the house and garden tour. It was very informative and it lasted about 30 minutes. It does include some very steep stair climbing but well worth the visit. I was not aware of the whole cat thing but it was an interesting story on why and how they got there. But to see where Hemingway, certainly one of America's best writers, lived was a very cool thing to do.... in this heat and humidity :)

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!

5 stars Way Better Than Just Another Bar Crawl! Listen, when…read moremy buddies started yapping about this Key West Ghost & Mysteries Tour, I was like, "Yeah, right ghosts in paradise? Pass the piña colada." I was already half-toasted from Duval Street happy hour, sweating in the humidity, thinking it'd be some cheesy, overpriced gimmick. But man, did it sneak up on me like a whisper in the dark. For what felt like pocket change (didn't even pay friends hooked it up), we wandered the shadowy backstreets of Old Town for 90 minutes, hearing wild true tales of haunted spots: the old firehouse with its dozen restless spirits (including a firefighter named Frank who still haunts the engine room), whispers from shipwrecked sailors on the breeze, and that creepy vibe from places tied to Key West's pirate past and yellow fever epidemics. The guide was a total pro mixing legit history with just enough eerie chills to make your skin prickle without going full horror movie. It's not scary-scary if you're buzzed and laughing with the group; it's more like deliciously mischievous storytelling that makes you glance over your shoulder at every creaky old conch house. What really sold it? Breaking from the usual beach-drink-repeat routine. Sure, Key West is all sun, sand, and rum, but slipping into the island's darker secrets cursed dolls like the infamous Robert, ghostly lights over the water from wrecked ships, and spots where the dead supposedly still linger felt refreshingly different and surprisingly fun. Highly recommend if you love a good story (and maybe a little liquid courage). The guide makes or breaks it, and ours was gold knowledgeable, funny, and just spooky enough to keep things lively. Bonus silly skit (because why not?): Me (whispering dramatically to my friends post-tour): "Guys... did you hear that? Footsteps behind us!" Friend 1: "Dude, that's just your flip-flops echoing." Me: "No, wait shh! It's Frank the firefighter... he wants his hose back!" Friend 2 (laughing): "Or maybe it's Robert the Doll, pissed we didn't say 'please' three times." All of us: "Run!" (We didn't run. We just hit the nearest bar for one more round. Ghosts approved.) Totally worth it. 5/5 even sober, I'd do it again.

If you're going to do a ghost tour--for the love of God, do it in Key West. Forget the cheesy ghost…read morewalks in cities that have to invent half their legends. This is Key West, where the humidity alone feels haunted, and half the locals already look like they've made peace with the afterlife. The Key West Ghosts & Mysteries Tour is the best of the bunch. You're not just shuffling along behind someone in a cape muttering about "orbs"--this is real-deal weird history. The streets themselves creak with old shipwreck stories, curses, and that doll (yes, that doll, Robert the Doll) who stares into your soul like he's still holding grudges from the 1900s. By the end of it, you're not sure if you're spooked by the stories or by the fact that people actually survived Key West before air conditioning. Pro tip: do it in the winter. In July, you'll be sweating so hard you'll mistake heat stroke for paranormal activity. In December, the air's crisp, the island's alive, and a walk through Old Town's lantern-lit streets feels like slipping between worlds. It's equal parts creepy, funny, and fascinating--a Key West cocktail mixed with history, ghosts, and just enough rum-soaked madness to keep you guessing.

We took this tour and had a wonderful time. We were guided to five restaurants and tried delicious…read morefood and drinks. The Cuban sandwich and key lime pie were to die for. We went to a cuban cigar making shop and some other shops we wouldn't have found on our own. Angie was an amazing tour guide. She was very knowledgeable about Key West. She kept us together, she kept us on the shady side of the street & followed traffic rules to keep us safe. I highly recommend this tour and suggest you ask for Angie.

My husband and I took the Historic Seaport Food Tour with GoGo and loved it. it started downtown…read morewith Shrimp cocktail and a glass of wine. Next we had Mahi Mahi tocos then continued our well paced walk to have the best lobster Mac & cheese. Our next stop was for a Cuban sandwich and then we finished with the best Key Lime Pie. I would highly recommend this tour with GoGo. He told us a lot of history and even took us to a Cuban cigar shop where you can actually see them making the cigars. You end up on Duval Street. very enjoyabl.

Charlie did a great job as a tour guide and explained everything around us very well...100% will…read morecome back

Awesome time ! 3 piece band was great w music and entertainment!…read more Staff were great and accommodating! Food was good and drinks cold! Highly recommended

Captain Matt and Tanner were great. Super informative about the wildlife, environment and kept the…read moremood light with jokes. Kids on board were able to feed a shark if they wanted to. They got us back to shore before heavy rains started. Would highly recommend!

As a filmmaker and photographer, I've documented a lot of different environments, but my experience…read morewith Key West Extreme Adventures was something special. This is a family-run business and you can feel that local, small-town pride from the moment you step on the boat. What impressed me most wasn't just the wildlife--though seeing bottle-nosed dolphins and sharks in their natural habitat was incredible--it was the professional camaraderie. Even though there are other tour companies out there, the captains are in constant communication, sharing sightings and even helping each other out with gear or debris in the water. It's rare to see that kind of collective stewardship in a competitive industry. The tour is also deeply educational. The guide did a fantastic job dispelling myths about sharks and explaining the biology of the animals (like the dermal denticles on their skin) with a level of respect that shows they aren't just using nature for a paycheck--they are actively protecting it. If you want an authentic, respectful, and insightful look at the Florida Keys' ecosystem, this tour is a must. I captured a large portion of our tour--including the sharks and dolphins--starting at the 2:26 mark in my vlog here: https://www.youtube.com/watch?v=og6BrVsB2QM