What To Do In Key West

No true tour of Florida would be complete without a drive down into the Florida Keys. After leaving the mainland south of Miami, we drove 100 miles southwest-ish down beautiful Florida Highway A1A (overlapping with US-1 the whole way). There’s really no way to describe how amazing the drive is. It’s one that you just need to take for yourself at some point in life.

While we were only there for 3 days and are trying to figure out how we can go back and spend some more time in the Keys to really explore all of the parks and culture of the place, here are a few ideas we can give you of what to do in Key West.

Covering everything there is to do here would be futile, especially in 3 days. Three months would give you a much better chance to “see it all,” including snorkeling or diving the reefs, going sailing, doing some fishing, going to Bahia-Honda State Park, partying your brains out, and taking the cruise to Dry Tortugas National Park.

Duval Street

Duval Street is where the main action happens in Key West. It runs the full north-to-south width of the island, barely more than a mile long. And it’s loaded with fun…restaurants, bars, shops, art stores, tours, and stores serving up Key Lime Pie (“Prevent Scurvy – Eat Key Lime Pie!”). Whatever you’re looking for in Key West, start on Duval St.

Sunset Celebration At Mallory Square

Two hours before sunset, head to Mallory Square at the northern end of Duval St. There, you’ll find street performers, musicians, people selling art, and food carts. And you’ll get one of the best vantage points to see the incredible sunset in Key West.

Higgs Beach Dog Park

If you’re traveling with your four-legged fur ball like we are, dog parks are a great place to get them some socialization and exercise. Higgs Beach Dog Park was Knox’s 4th dog park visit of the trip. This time he got his picture taken with Santa though.

Key West Dog Beach

Naturally, there are beaches all over Key West. At the corner of Vernon St and Waddell Ave is a beach where dogs can run leash-free and play in the ocean. Of course, Knox isn’t such a fan of water, so this wasn’t much use for us.

Hemingway House

On Whitehead St, you’ll find the house that Ernest Hemingway lived in while he was in Key West. It’s $12.50 per person for a tour, which we didn’t do. Whether you take the tour or not, you can catch a glimpse of the six-toed cats.

Chicken Watching

This one surprised us more than a little. All through the Keys, but mainly on Key West, there are feral chickens. Sometimes it’s two or three, sometimes it’s a flock of 20. You’ll hear them crowing at all times of the day. They’re protected though, so don’t plan on taking one home for dinner. You can try to refrain from the “why did the chicken cross the road” jokes, but it’s futile.

Southernmost Point

Go to the corner of Whitehead St and South St to find the Southernmost Point in the Continental United States. It’s not actually the southernmost point in the US, though it’s fairly close. It is the southernmost publicly accessible point in the Continental US. All other points south are privately owned or US military property. All that aside, it’s a major tourist attraction and worth venturing there to get a picture.

Look At The Trees

Aside from the palm trees, there are two trees in particular that you should see, both on Whitehead St (runs parallel to Duval St). The first is the banyan tree. The second is the kapok tree located at “The End Of The Rainbow” sign right by the Post Office. This obviously won’t take much of your time, but seeing the crazy root systems of these trees is worth the walk off of Duval St.

Smallest Bar In Key West

Have you ever been in a bar with only two seats? There’s a bar on Duval St that’s about as wide as two adults standing side by side. All that’s inside is a small bar with reggae blasting and a bartender that’ll serve you a tropical drink or two that’ll kick your buzz up quickly…for only $10 a pop. I’ve heard that if you stay for two drinks, you get control of the radio, though we didn’t stick around to test that claim.

Watch The Sun Rise & Set

Does this really need an explanation? Being on an island puts you in the unique position to see the sun rise over the ocean and set over the ocean all on the same day. Both are absolutely beautiful. Be sure to see at least one of each.


Here are pictures of most of the things you should see in Key West.