UPDATED 

Key West, Florida evokes images of turquoise waters, palm trees swaying under sunny skies, snorkeling, fishing, in short, just about anything to do with water. But, what if you don’t swim, don’t have a boat, and want to enjoy the scenery and whatever else Key West has to offer? Is there anything to do that doesn’t include water? 

Absolutely!  

Where is Key West?

Key West is part of the Florida Keys, a string of islands surrounded by the Atlantic Ocean and the Gulf of Mexico. It’s the southernmost city in the continental U.S. 

The main industry is tourism, and the locals know how to make the most of what their slice of paradise has to offer. Key West is a friendly place with cultural diversity, historic sites, and natural beauty. 

Here are my top 10 suggestions for things to do, that aren’t on the water. All of them are family-friendly, and most of them are free, or at least very affordable.

1. Old Town Trolley Tour

Once you arrive in the island city of Key West,  I recommend taking a tour with the Old Town Trolley Tours.  It’s a great way to get oriented to the island and the trolleys are open air.  You can buy a day pass and hop off and on as often as you like.

We stayed for the duration of the tour which was only an hour and a half long. Our guide was a native Floridian who grew up in Key West. I learned a lot from him and he was hilarious and gave a very in-depth tour. A highlight of the tour was learning about Duval Street, Key West’s main drag. Though it’s only about a mile long a lot is happening there. 

Be aware that there are several different trolley tour vendors and some are a bit more expensive than others. When you buy your ticket(s) make sure to ask what time the last tour leaves. You can hop on and hop off at most stops, but if you take the last tour of the day, you will be limited as to which stops you can get back on.

2. Key West Shipwreck Museum

Much of the culture of Key West developed around salvaging wrecked ships. It was once the main industry of the island and made Key West the richest city in Florida. To learn more about the shipwrecking industry check out the Key West Shipwreck Treasure Museum.

3. Take a bicycle tour of Key West

If a trolley tour isn’t your thing, tour the island by bicycle. Key West is small and compact, so riding a bicycle makes sense, as parking a car is a bit of a hassle (and you don’t need it). You can take a self-guided tour, or go with a tour company like Key Lime Bike Tours. Most bed and breakfast properties offer bike rentals and a map.

I recommend taking a self-guided bicycle tour after you’ve taken the guided trolley tour. I’m not getting a commission from the trolley tour company. I just think it’s smart to learn about the place you are visiting and I like orientation tours. 

4. Hemingway Home Museum

If you’re the literary type don’t miss Hemingway Home and Museum. Ernest Hemingway lived in Key West for over ten years. He completed A Farewell To Arms within seven weeks of moving to Key West.  The history of Key West and Hemingway is forever intertwined… if you’re a Hemingway fan, I think it’s a must-see. Besides, where else can you see six-toed cats?

5. Key West Lighthouse and Museum

Also on Whitehead St. is the Key West Lighthouse, now a museum. Climb the eighty-eight steps to the top for a wonderful 360-degree view of the island. There’s also a small museum that runs a short film about the history of the island and some of the original lighthouse keepers.

6. Take a photo at the Southernmost Point

It’s kitschy, but as you can see, people line up to take their photo next to the buoy at the Southernmost Point in the continental United States and North America. There is a stop for the Old Town Trolley nearby and you can get off, take your photo, then catch the next trolley. 

7. Where To Eat In Key West

Food is always a big part of a memorable trip. Whether it’s something simple like a refreshing gelato on a summer day or a regional dish that you won’t find anywhere else, a good meal is often the most cherished vacation memory. Key West has a bit of every type of cuisine with a strong Caribbean influence and lots of seafood.

The weekend I was in Key West was Lobster Fest weekend. As you might imagine, lobster is cooked in every way imaginable.  I tried the honey tempura-battered, deep-fried lobster on a stick, and lobster mac and cheese. I’m a traditionalist and prefer my lobster steamed or grilled with butter, but the lobster mac and cheese was delicious. 

Duetto

For dessert, I couldn’t resist checking out Duetto, a real Italian gelato and coffee shop. The owner is originally from the Piemonte region of Italy. My travel companion, who just happens to be from Italy, had an espresso and pronounced it the real deal. I had a pistachio gelato – tasty – but I still think it tastes better in Italy.

Kermit’s Key Lime Pie

Right by the Marina is Kermit’s Key Lime Pie. Kermit sells just about anything key lime you can think of and you can sample all of it.  You can also buy a slice of key lime pie to go or eat it on their patio.

8. Walk around the marina

Just because you don’t have a boat doesn’t mean you can’t enjoy walking around the marina. There are shops and restaurants, and you never know you may see some famous people there.

I like to read the names of the boats and see what flags they are flying. It’s also fun to just observe people who live and work on boats – such a different lifestyle.

9.  Key West Sunset at Mallory Square

For the quintessential Key West experience, watch the sunset at Mallory Square. At about 6:00 pm the square fills with the sound of live music, street performers and entertainers of all varieties, but I was mesmerized by the sunset and watching the boats sail by.

10. Take an architecture walk

Key West architecture is characterized by bright pastel colors, wraparound porches, and ornate latticework.  Take a walk and discover the historic homes and the oldest house in Key West. The historic area is six-blocks and listed on the National Register of Historic Places.  Walking around Key West is one of the best things to do. A unique blend of history, surrounded by gorgeous scenery, the best way to enjoy Key West is as you like. 

I think that’s at least ten things you can do, and never put even your big toe into the water. The best time for a Key West vacation is any time really, but summer will be very hot and crowded. Consider visiting between fall and winter or winter and spring.