Key West · GUIDED
15 reviewed
Out of 15 guided tours on this site, these 15 are the ones to book. Prices, durations and the standout details are all here — choose in five minutes, then get back to the beach.
Pedal Old Town Key West on a guided 2-hour bike tour with bottled water and key lime pie. Visit Mallory Square and the Southernmost Point.
“. Riding bikes with Lenny our guide as we learned about Key West history was an awesome experience! 😊 The key lime 🍋🟩 was great!”
A 90-minute nighttime Key West ghost walk with stories at Hemingway sites, churches, and the Hard Rock Cafe, plus dowsing rods.
“We enjoyed the ghost and mysteries guided tour. Ted was a great guide and knowledgeable of the history of Key West and its happenings. Thank you”
Glide a 100% clear kayak through Sugarloaf Key mangroves near Key West, guided by experts who help you spot wildlife below the surface.
“Victoria was excellent and enthusiastic. Somewhat hard to spot fish unless they are under your plexiglass kayak”
Small-group Key West dolphin watching and guided snorkeling aboard a catamaran with snacks, reef-life tips, and patient instruction.
“Excellent guides , educational & fun. 4 hrs was the right amount of time. Dolphins were serene to watch, but the sharks were a nice surprise.”
Kayak and guided snorkel through Key West mangroves with Honest Eco, plus a morning sail, organic snacks, and wildlife spotting.
“It was a very well put together tour, very enjoyable with activity but also some time to just relax and cruise. Libby and Angela were super friendly and clearly know their stuff, but also were just fun to chat with. Lunch was great as well!”
Ride Key West by bike with a guide, hit Old Town sights and Southernmost Point photos, then end with award-winning key lime pie.
“James was a great tour guide! Shared lots of information with our group about the history of Key West and even helped take pictures of us at the southernmost point! Great value for the money, good way to see the island and not too strenuous.”
Ride the Trolley of the Doomed through Old Town Key West, hear ghostly tales, visit Shipwreck Treasures Museum, and laugh through it.
“Salty and Eric were great story tellers they made the tour fantastic i learned a great deal”
LED-lit clear kayaks in Key West’s luminous lagoon. Guided 2-hour night ride for wildlife viewing from mangroves.
“Such a unique way to see the Keys, I would highly recommend for an unforgettable experience that is like nothing else. We saw fish, sharks, and manatee! The kayaks can get a little wet from the paddle dripping, but that was it. I was in jeans and barefoot and was dry before dinner afterwards. DO NOT skip this just because you don't think you have the right clothes/shoes. You'll be fine in whatever!”
A 1-hour guided visit to the Truman Little White House in Key West. See Eisenhower and Edison connections for $25.
“I knew nothing of Truman little white house before our Key West vacation. Definitely a must see! A trolley tour stop does not do justice to this important piece of Americana history. Vice President Truman was left totally in the dark concerning the atom bomb before FDR’s death. I left this tour with a much broader knowledge of not only learning about this great man but a better understanding of the ending of WW2.”
GPS audio walk through Key West’s Old Town past Mallory Square, Truman, Hemingway, and the Southernmost Point, with lifetime access for $11.24.
“This was a self paced tour of Key West. We made several stops along the way and detoured off the path. We enjoyed the tour and learned more about Key West than we would have on our own. We would highly recommend.”
A low-cost, self-guided Key West walk with GPS-triggered stories, offline audio, and major Duval Street landmarks in 2–3 hours.
“wonderful idea and interesting facts. We passed a lot of places that we were surprised were not on tour. They looked historical but I guess you can't put everything there. Had problems with phone with tour but it could be on my end. Didn't get to finish”
Kayak or paddleboard through Key West mangroves with a small group, expert habitat talk, and easy pickup/drop-off for a 2-hour eco outing.
“We had a great and chill time on our tour. We saw plenty of creatures and soaked in all the things Kristen had to share. Also, getting picked up and dropped off was so helpful and our shuttle drivers were friendly and gave us great tips while visiting! The owner was great and super trustworthy, so don’t be afraid to look at their site directly!”
A $9.75 self-guided Key West ghost walk using the WalknTours app with GPS and an optional EMF reader.
“It was fun and nice that we could do it when we wanted to. It came with good directions which was important since we were in a new place.”
A smartphone audio walk through Key West’s landmarks and lesser-known stops, paced your way, for $9.75. Starts at the Custom House.
“You can go at your own pace. If you want to stop and explore a certain spot, you can pause the tour. It's very easy to follow and give lots of good info!!”
Self-guided audio walk from Mallory Square to Southernmost Point, mixing Key West landmarks, pirate treasure lore, and optional museum visits.
