5 Must-Do Things in Key West

I’ve mentioned it before on the blog that my hubby is a coastal engineer and he travels to the Florida Keys on a regular basis for his job. In case you didn’t know, the Keys are a string of islands at the very southern tip of Florida that are connected by bridges and causeways.

I try to tag along with hubby when I can. Over the years we’ve discovered a few things we like to do when we are there. I’ve shared my 5 Must-Do Things in Key Largo, the northernmost Key. Today I will share what my must-dos are for Key West, the southernmost Key.

5 Must-Do Things in Key West5 Must-Do Things in Key West

1. Explore the Streets

One of my favorite ways to visit a town is to go for a run through it. You get an up-close-and-personal perspective of the place when you travel by foot. However, not everyone likes to do that. Luckily there are a number of ways to explore the island, from bike and moped rentals to the Conch Train tour. Below are my favorite streets and a few things you can find on each:

  • Duval Street –
    This is a Walgreens!
    This building technically belongs to Cuba!
    A church feels a little out of place on this street…

    Duval Street is the Bourbon Street of Key West. Lots of bars, shops, boutiques and stores are located on this very walkable street.

  • South Street

    South Street is where you’ll find “the southernmost” everything.  It’s the southernmost point in the United States. Don’t you love superlatives? I do 🙂

  • Whitehead Street

    On the corner of Whitehead Street and Truman Ave you’ll find the Key West Lighthouse. I love to visit lighthouses. This one is the first on our Lighthouse Trail!There’s a bit of a climb to reach the top. Either 88 steps or 98 depending on the source you read. I didn’t count them this time.( I usually do.)When you reach the top you are rewarded with beautiful views of the island and the ocean.A little further on you’ll find the Ernest Hemingway Home and Museum. The Green Parrot Bar is also located on this street.

2. Bars

Key West is famous for being a party town. Even if you are a teetotaler, you can still walk in and visit some of these historical places. Some of my favorites:

3. Places of Historical Interest

There are quite a few places you could visit if you are a history buff. Some of my favorites include:

  • Hemmingway House –

    Hemmingway used to live here, in this house. The six-toed cats that also live here are descended from his originals.

  • Mel Fisher’s Museum

    When the kids were little we loved visiting this museum. Mel Fisher was a treasure hunter who spent 16 years searching for the wreak of a Spanish ship called the Atocha. It houses the treasure found on that ship.

  • Custom House

    I haven’t been inside the recently restored custom house but it houses a museum with exhibits. Next time…


  • Key West Lighthouse
  • Harry Truman’s Little White House

    I have not been here before either but have passed by it many times. More to see next time we come!

There are also two forts on the island that I’ve never toured: Fort East Martello and Fort Zachary Taylor State Park (we have been swimming here before, just not on this last trip.)

4. Food

This is one of the reasons I like to travel: to experience the local cuisine. Clearly, the Keys are known for their seafood. They are also known for Cuban food since there are a lot of Cubans living in south Florida. And of course Key Lime everything. Below are some new favorite places!

  • Hogfish Bar and Grill

    Have you ever had hogfish? I am NOT a big seafood eater but this is my new favorite kind of fish. Unfortunately it’s local and not easy to find in other places. If you ever see it on the menu, try it! It’s not fishy at all!

  • El Sibonay

    This is my favorite Cuban restaurant in the Keys. We go just about every time we make it to Key West. It’s a little tricky to find since it’s in a neighborhood. Try the Palomilla steak and fried plantains!

  • Pirate seafood
    They can’t have permanent tables so they use ironing boards! How clever!
    I have no idea what that sauce was but it was delicious!

    This is a new find and I am so glad we found it! It’s actually a food truck in the Chevron gas station parking lot. I had the special of the day: triple tail tacos. Another fish I’d never had before but boy was it good! I had mine without the tortilla. I didn’t realize they would come with fries but they were pretty tasty! The avocado/tomato pico de gallo on top was fantastic as was the lemon mayo dip. My mouth is watering just thinking about it!

  • Bodega Santiago

We found this place on Yelp and were blown away by how good the food was! It’s a tapas place so we split the spring salad with duck confit, pinchos modunos (I have GOT to try these at home!) and the chicken skewers. We drank VOS sparkling water which is my new favorite brand of sparkling water!

We dug right into the pork and chicken that I forgot to take a picture. Oops! You can trust me: they were amazing!

  • Anna’s Cuban Cafe

    For the best Cuban coffee in town, head to this little place near the Southernmost Point. You walk up and order at the window then sit outside and sweat enjoy the breeze. We usually get café con leche but decided to try the colada this time. So good! It’s basically an espresso. The fresh fruit salad comes with mango, banana, papaya, and watermelon.

 5. Sunset (and crazies) on Mallory Square

At the end of Duval Street you’ll find Sunset Pier which leads out to Mallory Square where everyone congregates to watch the sunset. It’s also where the cruise ships dock. 

That’s the crazy cat-guy from our hotel balcony. His cats do all sorts of tricks. The guy himself is a bit of a character.
It’s crazy to see this huge ship pull right up to the dock!

Pretty tame early in the morning. There are roosters everywhere. But at night it’s a pretty busy place with vendors of all sorts. If you ever visit, you have to catch the crazy, cat-guy’s show. He has quite an act. The weather wasn’t good on this trip but here’s a sunset from a previous trip. 

Honorable Mentions

The vegetation is gorgeous down here! I love the little gardens you can spy as you explore around. Check out the size of this banyan tree located on Whitehead Street! 

And this cool Kapok tree a little further down by the post office.

My favorite place to stay is the Casa Marina Hotel. We’ve been coming here for years (with work! It’s a big splurge otherwise!) It has been remodeled since the last time I was here but they maintained the original feel of the place.

The lobby is very elegant.
We requested a room in the “old” section. There’s a new section too where they added on additional room.

I would be doing you a disservice if I didn’t mention key lime pie. I make it at home all the time but my favorite version to get down here is the frozen key lime pie on a stick (it’s dipped in dark chocolate!) Look for these signs:

There you have it! Have you been to Key West before? What would you add to my list? What favorite did I leave off? If you’ve never been to the Keys I would encourage you to go! It’s the Caribbean that you can DRIVE to!!

About Sheila @ Making the Most of Every Day

I'm a wife, mom, and a homeschool teacher. I'm always behind on housework and paper pile sorting. I'm fond of this crazy life but not of melted cheese. I want to follow hard after God, making each day really count. I like to run, read, cook (and eat!). Thanks for joining along on my journey!

4 thoughts on “5 Must-Do Things in Key West

  1. Sheila – I am smiling reading your blog! My husband and I just got back from Key West 2 weeks ago and we saw alot that you mentioned! I highly recommend anyone planning a vacation there! We enjoyed our weeks stay there. So much to do and alot of fun! Thank you for sharing!

  2. Very good post. What time of year do you recommend visiting the keys. Are there times when it’s less crowded? Thanks again.

    1. Winter is the high season because all the northerners want to escape the cold! I like the spring because it’s less crowded and the heat of summer hasn’t hit. We went on June and although it’s pretty warm it was the least crowded I’ve seen it! Stay tuned for another Keys post coming soon!

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