6 Things to Do in Key West

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Key West: where the weird are always welcome. This off-the-wall, eclectic & open-minded community is bustling with personality.  And whether you’re visiting for a long weekend or the whole week, there’s a handful of things you just have to experience. Without further ado..here are the 6 things to do in Key West!

Things to do in Key West, let’s get started!

1. Take a Tour of Ernest Hemingway’s House

There’s no friend as loyal as a book, Ernest Hemingway once said. The famed author spent many years in Key West, overcoming writer’s block & drinking his worries away with friends. Hemingway is famous for books like For Whom the Bell Tolls, A Farewell to Arms and The Old Man and the Sea, and during his ten-year tenure in Key West, he lived at 907 Whitehead Street. Walking into The Hemingway House is like stepping back in time. Original furniture and decor still fills the home. Descendants of Hemingway’s six-toed cats roam the property. The original 1930’s in-ground swimming pool (a major feat at the time) still remains glistening in the summer sun. The museum is open every day from 9 to 5 and tickets ($18) can only be purchased with cash upon arrival. It’s one of my favorite places to visit! Looking for things to do in Key West? This is a great place to start.

Ernest Hemingway’s House

2. Eat to Your Heart’s Content

Blue Heaven

To find Caribbean cuisine, look no further than Blue Heaven. Their menu is ever changing, but you can find a few staples like Jamaican jerk chicken and fresh yellowtail snapper on their dinner menu. The restaurant is tucked under vibrant trees and hidden from the hustle & bustle of Duval Street.

La Creperie French Cafe

Right across the street from Blue Heaven is La Creperie French Cafe. I highly recommend stopping here for breakfast because it is to die for!! You won’t find crepes like this anywhere else on the island. The crepes are filled with fresh & organic ingredients, drinks are served in up-cycled mason jars, and straws & to-go materials are completely biodegradable. This makes La Creperie one of the first eco-friendly restaurants in the Florida Keys.


For a more formal option (you know, where shoes & shirts are necessary) try Latitudes, on Sunset Key. A short ferry ride will take you to the oceanfront restaurant. Here, of course, you’ll find the freshest fish and seafood. The lobster bisque is my personal favorite. Pro tip: make sure to book your reservation for dinner time, because there’s nothing more beautiful than a sunset in Key West.

Moondog Cafe and Bakery

Located away from the crowds of Duval is Moondog Cafe and Bakery. It’s a lesser visited restaurant but one that warrants a visit. Eggs Benedict’s, omelets and blueberry lemon quinoa pancakes are a few of the mouth watering options on the breakfast menu (though the modest restaurant offers lunch and dinner too!) 

The Breakfast Club, Too

Breakfast places are kind of my thing on vacation so keeping on brand, The Breakfast Club, Too is a must stop. I was sold while perusing the menu when I found the silver dollar charcuterie board!! This quaint spot is over near the wharf on the north side of the island and is newer to town (though very much loved!) Be sure to get there early as they don’t take reservations and waits can be long. 

3. Experience Iconic Key West Nightlife

Duval Street

Duval Street is the Key West equivalent to New Orleans’ Bourbon Street or Nashville’s Broadway – but better! This is where the greats came to drown their sorrows & celebrate their accomplishments. Ernest Hemingway, Truman Capote and Jimmy Buffett were a few to seek refuge in the local bars. Today, many people take on their own “duval crawl” and bar hop till the sun comes up. Key West has open container laws so you can take your beer to go! Everything is very walkable, there’s never a need to drive anyways.

Might I suggest the following:

  1. A self-proclaimed “sunny place for shady people,” The Green Parrot is one of the oldest bars on U.S. Route 1. What started out as a grocery store in 1890 morphed into one of the rowdiest and well known bars in Florida. If you want to drink like a local, head to the Green Parrot.
  2. Hog’s Breath is a popular hangout in town. This watering hole has been a staple in the community for almost 25 years. Great food, great drinks & fantastic live music. Kenny Chensey has been known to give free concerts here. And as they say, hog’s breath is better than no breath at all!
  3. My personal favorite is a place where Hemingway frequented, Captain Tony’s Saloon (though it was named Sloppy Joe’s at the time – but keep reading, I’ll get there). The bar was bought by local boat captain Tony Tarracino in 1958, and affectionately named Captain Tony’s saloon. You could find Tony at the bar every week, even after he sold it and up until he passed away in 2008. Inside expect to see dollar bills, business cards, license plates & bras stapled to the walls and ceilings, along with some pretty strong drinks. Captain Tony’s was also where Jimmy Buffett got his start. Before he made it big, he sang here & was paid in tequila.

4. In order to truly understand the essence of Sloppy Joe’s in Key West, you have to go back to December 5, 1933 – the day prohibition was repealed. It’s also the day Sloppy Joe’s served its first beer. Originally located on Greene Street, the bar quite literally up & moved in 1937 when the landlord raised the rent. The owner, local patrons & employees picked up their drinks – and all the furniture – and moved to a vacant building on duval street, where it proudly stands today. Because Hemingway was basically a permanent fixture there, they hold a “papa look-alike” contest every year where Hemingway’s relatives crown the best impersonator.

5. Irish bars don’t really need an introduction and Irish Kevin’s is no different. I mean, their motto is “I came, I drank, I don’t remember.” Loud and hilariously funny, this joint plays great live music. The performers tend to heckle the crowd which makes for the best experience. The crown jewel here is the chandelier composed of Jameson bottles. 

6. The World’s Smallest Bar – and it’s small, only 72 square feet – lives on Duval and has the biggest energy in town. Stop by and grab a drink (it’s about all you can do!) But be warned – the Key Lime Pie shots are tasty but dangerous if you have one too many!

4. Snap a Photo at the Southernmost Point

Did you know that in Key West, you’re closer to Cuba than you are to Miami? There’s a vividly painted buoy to designate the southernmost point of the continental United States. this screams TOURIST but it’s the perfect photo-op! stop by the Southernmost House Hotel for a drink before you wait in line for a photo. The old Victorian home is a bed & breakfast with killer drinks & amazing oceanfront views.

5. Enjoy Breathtaking Sunsets at Mallory Square

Mallory Square is one of Key West premier attractions with street performers, local artists and artisans and incredible views of the setting sun. Huge crowds gather every night just to enjoy the sunset. Mallory Square is also home to the Key West Aquarium and the Key West Shipwreck Treasures Museum.

6. Sit in the Sun — Duh!

If you’re in Key West, chances are you’re there to soak up the sun. Smathers Beach is the largest public beach — and most popular — on the island. Chair and umbrella rentals are available but can get pricey if you’re staying a whole week (I would suggest bringing your own or buying some at a convenient store). The half-mile of shoreline provides stunning views of the Atlantic.  

Looking for things to do in Key West on your next trip or on Spring Break? Hope these recommendations can kick-off your trip! Let us know where you end up going in the comments below!