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.

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.

This was a last minute decision for us on our stop in Key West. It sounded like fun and to be…read morehonest, it was better than expected. The guide was funny, knowledgeable and kept us entertained the entire trip around the Island. There is another tour bus but it doesn't go around the whole island so be aware of what your buying if you go on another bus. This tour bus allows you to jump off and on all day at the 13 well marked stops they have around the Island. For us it was worth every penny. Enjoy!

Absolutely reserve Anthony for a private boat trip while in the Keys. From start to finish this…read moretrip was amazing for my family. Anthony's boat is top notch, all the equipment is new and nice (paddle boards, masks, etc). Anthony's knowledge and experience of navigating the Key's waterways is outstanding; your family will be safe on this trip! We will definitely book again.

Captain Anthony and his pup Mystic were the highlight of our trip! Perfect boat to go to the sand…read morebars in and float in the beautiful water. Fits 6 guests very comfortably and plenty of storage area for your bags. Giant cooler filled with ice was the perfect touch.

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.

Key West Food Tours was a great experience with a variety food and drink samplings and walking tour…read moreof a few KW neighborhoods, with a bit of history mixed-in. Kyle, our guide for the day, was great and talked about Key West's past and present and local customs, including its major industries throughout the years (cigars, rum, ship wrecking [which to me sounds similar to Ransomware today] and more), the common use of Bahaman light blue believed to ward off evil spirts and also birds (not evil but can make a mess), and tour of Gato and Old Town, parts of town that you'd normally not know about as a tourist. He also made sure everyone was hydrated and had multiple chances to cool off as it was a humid, sunny afternoon. The food stops included El Siboney for Cuban pork, beans and rice, bread and plantains, The Rum Bar for an iced rum drink, Mangoes for conch fritters and tomato based conch chowder, Kaya for mahi mahi and, to finish it off, Cuban Coffee Queen for Cuban espresso and key lime pie. We met people from all over including Spokane, WA, Minneapolis, MN, and other parts of Florida.

Sailing at its best. Great craft but more importantly great Captain…read more Thank you Chazz for making us feel so happy, unforgettable BD gift for my wife. Maybe we see you in North Carolina or is it South?

I booked Capt Chazz for a sailing with my family and we all walked away grinning ear to ear. We…read morebooked a 3 hour sail and my only regret is we didn't book a longer sailing. I highly recommend you book a with this Capt, he will make sure you and your party have a great time.

Lloyd's bike tour is fun. He is a character that's has lived in Key West since the 1970'S. He'll…read moretake you to spots in Oldtown you'd never find on your own. Lloyd will open a coconut with his machete and you'll get to taste the coconut's water and its meat. We visited a fabulous tropical garden that's inside a civil war fort. My wife and I thoroughly enjoyed Lloyd's 2 hour long bike tour of "Old Town" Key West aka the Conch Republic.

Lloyd gives you the ins and outs facts about Key West and the local culture. This is my second time…read moretaking his tour, and I highly recommend it!

We had a perfect trip at Looe Key. Calm seas, sunny day, crystal clear water at our 20' anchorage…read more Captain Eric was excellent in his knowledge of the area and had the expertise for a fun and fantastic outing. His boat was awesome too!