Don’t miss all these fun things to do in Key West — the most popular part of the Florida Keys!
During our 4 day Florida Keys itinerary, we spent half of them in Key West. While each area along the way from Miami has something unique, it’s Key West that’s really the area with the most to do in one area.
18 Fun Things to Do in Key West
1. Stay on a Sailboat!
While there are a lot of gorgeous hotels in Key West, if you’re on a budget, why not stay a little out of the downtown area on a sailboat? Stock Island is one of the last areas in the Keys that allows Airbnb, and most of those listings are sailboats! I like where we stayed because you don’t have to kayak out to it…
2. Eat your weight at Turtle Kraals
YUM! Turtle Kraals has some of the best food we ate in the Keys. We started off with some drinks, a key lime margarita and virgin Miami vice, beer-steamed shrimp, Key West ceviche, a fisherman sandwich and tacos, some stone crabs, and then a Key Lime pie and banana bread pudding. A LOT!
If there’s one thing you must try at Turtle Kraals, it’s the ceviche. We, of course, only had the Key West one, but you can get a sampler flight to try all of them. Apparently when Curtis Stone visited from the Food Network, he ate two whole flights. The KW one is special as it’s made with hogfish, which is considered the “filet mignon of the sea.”
3. Try Everything Related to Key Lime Pie
If you go to the Keys and don’t try anything key lime, you’re missing out! For those that haven’t ever tried it, key lime pie is a delicious and tart dessert mostly made with key lime juice, condensed milk, and egg yolks. Besides pie, you can try milkshakes, ice cream, and more! I remember having the key lime milkshakes after swim practice back when I was in the Keys for training.
We had key lime pie at a few places during our Florida Keys itinerary, and in Key West we specifically had it at Turtle Kraals. Theirs isn’t as tart, which made me like it a lot more!
You could even do this fun bike tour as it comes with key lime pie at the end as a treat!
4. Grab a chill breakfast at Fisherman’s Cafe
For a more relaxed morning, head over to Fisherman’s Cafe. If you go decently early, you’ll be by the harbor when it’s still pretty quiet and only the locals are getting up to their business. Enjoy the fresh squeezed orange juice with your breakfast sandwich!
5. Climb Up the Key West Lighthouse for the Best Views
For some really nice views of Key West and out to the sea, you’ll want to climb up the Key West Lighthouse! Before you go up, pop into the museum to get more of its history.
6. Pet all the Kitties in Earnest Hemingway’s Home
While you’re in the area, cross the street and head over to Earnest Hemingway’s home! Hemingway called this place home from 1931 to 1939, and you can read more of is life in Key West through the house’s well preserved rooms.
It’s pretty cool to learn a bit more about one of the US’s most famous writers. However, the real attraction is all the kitties who rule the roost! Fran and I may have gone a little cat-lady crazy.
7. Watch the Sunset from Mallory Square
For the best sunset views from land, head down to the bustling Mallory Square! If you want to treat yourself a bit, get these fun pineapple drinks and sit at the edge by the water for the best sunset views.
8. Or… Enjoy the Sunset Views from a Sailboat… with Wine
Now for the best sunset views from the water… go on a sunset sailboat cruise! We went on one with Danger Charters, and had a blast. The food was delicious, and Fran thought the wine was good too (I just had a soda).
If you want to be able to eat the food after it’s done its rounds, sit by the entrance to the bottom of the boat. They leave the platters right there for anyone to pick at later!
9. Go snap a pic of the Southernmost Point
By far one of the most touristy things to do in Key West is checking out the iconic Southernmost Point! If you want a photo of yourself with the landmark, be prepared to stand in a line. Neither Fran or I cared either way, so I snapped my photo while people in line switched positions.
10. See the Southernmost House
The Southernmost House was once a huge mansion and as you might guess from the name, it was once considered the southernmost house in the continental United States. The mansion was built in 1897 in a Queen Anne Victorian style, and, fun fact, it was the first home in the Key West to have electricity! Thomas Edison himself oversaw the installation.
The mansion has more fun history, like its role as a speakeasy during Prohibition or its role as Cafe Cayo Hueso nightclub in the 1940s. Though after these few decades of seedier uses, it was completely renovated to something more respectable, and would later host presidents Truman, Eisenhower, Kennedy, Nixon, and Carter.
Today it’s a bed and breakfast and, yes, you can stay here yourself! Click here to book a stay.
11. Take a Trolley Tour
If you want to hit up a lot of the big things to do in Key West, then take the hop-on, hop-off trolley tour. It starts at Mallory Square, goes all round Key West, and stops at many spots on the list. Just makes sure to keep your boarding pass on you has sometimes the sticker isn’t enough. Get tickets here
12. Get some coffee at Cuban Coffee Queen
We saw Cuban Coffee Queen at night when it was closed, and Fran remembered how much her husband loved this place when they went, so naturally we had to stop by for coffee the next morning…. and the morning before we drove back haha. It really is delicious! Bonus — there’s a fun “Greetings from Key West” sign on the side!
13. Pop into Books & Books @ The Studios of Key West
I always like visiting bookstores, so one our first afternoon in Key West, we stopped at Books & Books @ The Studios of Key West as we were walking around downtown. I wound up getting a very cute postcard set of all these famous bookstores around the world.
14. Learn Why Key West is Called Conch Republic
We learned this fun fact on our trolley tour. Have you seen the random signs around Key West that refer to it as the Conch Republic? Well, there’s a good reason, and Key West considers itself the only republic to successfully secede from the Union.
Back in 1982, the US Border Patrol set shop along US 1 to check cars for narcotics and illegal immigrants. Since US 1 is the only road connecting Key West to the US, you can imagine it caused quite the annoying traffic jam that hindered tourism and probably annoyed everyone, locals and visitors alike.
Well, after the government refused to listen to the city council’s complaints and they couldn’t get an injunction to stop Border Control, the mayor at the time declared independence on April 23, 1982, taking the name Conch Republic and referring to its citizens as Conchs.
After declaring war on the US for all of one minute, they surrendered and asked for a billion dollars in foreign aid! While the secession probably wasn’t as, ahem, official as the Confederacy’s attempt in the 1800s, the Conch Republic still considers itself, jokingly, independent, which is why one of their slogans is “We seceded where others failed.”
15. Check Out the Statues Around Custom House
Because the meeting point for our sunset cruise was around here, we had some time to kill and walked round to see all the interesting statues.
The Custom House itself is a museum and the HQ of the Key West Art & Historical Society, so the statues make sense. You can see about a dozen of them and they’re all created by Seward Johnson.
16. Walk around and do some shopping!
Downtown has a lot of fun little shops and boutiques. When my purse broke, we had to pop into a bunch to find a replacement, so I actually did wind up shopping more than I normally would when traveling!
17. See St. Paul’s Episcopal Church
St. Paul’s Episcopal Church is a very pretty white church that dates back to 1832 and is the oldest church in South Florida, though this current building is the 4th of its kind. Admire from the outside or go in for a service! If you do want to attend a service, you can check their schedule here.
18. Try some pralines.
While we were downtown, we tried one of the praline samples at this fun store, called Savannah’s Candy Kitchen. And, of course, one bite and we needed to buy some to eat even more! Well played, well played.
19. See all the chickens!
It shouldn’t take you long to spot them, but there are sassy, colorful chickens hanging out all around Key West. Key West is a no-kill island, and these guys know it. Just see them struttin’ around not like they own the place, but because they totally do (just like the cats are the true owners of the Hemingway House). The cutest sight, of course, is the mama chicken with all her baby chicks!
More Things to Do in Key West That I Didn’t Get To
20. See Truman’s Little White House
During is presidency, Truman spent 175 days at this home in Key West over the course of 11 visits. The house itself was first built in 1890 and before Truman visited in 1946, it hosted President Taft and Thomas Edison.
Truman was in Key West because, after 19 months in office, his doctor ordered him to get some rest somewhere warm. I mean he was president for the end of the last huge war the world has seen, so… I imagine he was not well. Also have you been to Washington DC in the winter? It’s horrible.
Because Truman believed that wherever the President was, the White House was (he’s probably regretting that statement now), he began calling his Key West home, the White House, and its nickname became the Little White House.
Later, other presidents would visit the Little White House, including Eisenhower, JFK and later Carter and Clinton. It was also used as the Naval Station Commandant’s home until 1974, and then in1987 Florida took over and turned it into a museum, which you can visit today! Book a tour here
21. Mile Marker 0
So the US-1 Highway, goes all the way from Key West to Fort Kent, Maine, right at the Canadian border. It’s the longest N-S road in the US. One of the quirky things to see is the Mile 0 marker, which marks the very beginning of US-1. I mean, I feel like we passed it and if we didn’t, we saw plenty of bright green souvenirs with Mile 0 on them. It looks like every other green mile marker sign you see in the US, so, you know, not really worth going out of your way for.
22. Check Out the Oldest House
While we passed by the Oldest House while we were out, we didn’t actually stop in to check it out. It looks pretty unassuming from the outside! It’s not the oldest house in the country, but it is the oldest in South Florida, having been built in 1829. It does look like a cool little museum on the inside, so if I ever find myself back in the Key West, I’ll make sure to stop in!
23. Kayak Near the Sand Key Lighthouse
This is something Fran did when she came with her husband, and I’d want to do if I came back! The Sand Key Lighthouse is a unique looking lighthouse that sits nearly 7 miles (11km) from the southwest of Key West. From all the photos I’ve seen, it literally looks like it’s in the middle of the water.
It’s built on sand and once there was even a lighthouse keeper’s quarters within. During normal weather, there was a mini island around the lighthouse, however once hurricanes hit, it sunk everything from the attempt at a storm wall to the actual keeper’s quarters.
Obviously, no one lives there today, but you can often snorkel or kayak nearby.
24. Spend the day out at Dry Tortugas National Park
Fran and her husband went camping at Dry Tortugas, and while I would have loved to visit, it was too difficult to squeeze it in with our schedule. The island is 68 miles (109km) away from Key West, so definitely not close.
The park itself is mainly made of Fort Jefferson and seven tiny islands. It was “founded” back in 1513 by none other than Juan Ponce de León himself, and named it Tortugas after catching 160 sea turtles there. “Dry” was added because of the lack of fresh water. While the fort was worked on from 1847 through the Civil War, they eventually stopped and turned it into a military prison instead until 1874.
The real charm of Dry Tortugas, though, is the wildlife above in the air and below the sea that surrounds the islands. This makes it a lovely place to indulge in some bird-watching, snorkeling, or swimming! Book a tour here via a catamaran
25. Check Out Other Museums & Attractions
There are a lots of other fun museums and attractions around the Key West, especially if you’re coming with kids. The Key West Shipwreck Treasure Museum is exactly what it sounds like.
The Mel Fisher Maritime Museum features artifacts from the 1622 recovered treasure fleet and goes into Key West’s role in less savory topics like the transatlantic slave trade and piracy.
Key West Aquarium has been round since 1935. And of course, there’s the beautiful Key West Butterfly & Nature Observatory.
How to Get to Key West
Technically, there is a Key West International Airport (EWY), but it’s a lot more expensive than just flying into Miami and renting a car. Plus, with a car you’ll see the other main stops o the Florida Keys.
While I think your best bet is to drive down yourself, it is possible to book a shuttle from Miami. This shuttle is for day trips, but try emailing and see if can just stay behind if you want to be in Key West longer.
Rent an RV
Key West is about 3 hours from Miami and 2 hours from Key Largo. It’s pretty expensive all around, so if you want to cut down on accommodation costs, try renting an RV for your trip and finding campgrounds! Then use the taxis or Lyft to get into town.
I have a guide on where to stay in the Florida Keys that highlights campgrounds as well as hotels!
What would add to this list of fun things to do in Key West? Let me know!
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Disclosure: I worked with Florida Keys & Key West, so many of my meals and activities were covered. However, all opinions are my own.