A Weekend in Key West

key west

A visit to South Florida is not truly complete without a stop in Key West. The southernmost key is a mix of relaxing island paradise and party destination.

Though the drive from Miami is 3.5 hours long, sometimes longer during popular weekends, it’s totally worth it. If you’re driving, there are plenty of great places to stop along the way for a bite. If you want to get your seafood on, you can stop literally anywhere for crab cakes or fish.

But my personal favorite is M.E.A.T. Eatery and Taproom, which is in Islamorada. Their burgers are nationally known (because they were on the Food Network), and they have a great selection of beers. The beer cheese soup is also out of this world.

Friday Night

The good thing about eating on the way to Key West instead of when you get there, is that by the time you finish the drive and check in to your accommodations, you’ll be ready to drink. If your main goal for the weekend is to go out, then you’ll want to stay as close to Duval Street as possible. Though you can always take a cab or an Uber, it’s a small island, and traffic can get bad around the popular areas, so you don’t want to get stuck waiting for a ride.

If you’ve never been to Key West, this is a good night to walk up and down Duval Street and take it all in. It’s the closest thing Florida has to Bourbon Street, except with a more island feel. There are plenty of bars with outdoor patios so you can enjoy the sea breeze while you get your drink on. Sloppy Joe’s is a particularly popular one with live music all day long. This may be a good place to end your night after you’ve made your rounds through Hog’s Breath Saloon and Irish Kevin’s.

key west duval street
This is Duval Street during Fantasy Fest, but you get the idea…

Saturday

The second best place to have breakfast in Key West is Sarabeth’s (the first, you have to save for Sunday). This is a great place to enjoy lemon ricotta pancakes or a bacon and shrimp omelette with your morning mimosas. It’s less than 10 minutes walking to your next stop of the day: The Hemingway House.

The Hemingway Home and Museum is one of the Keys’ most popular attractions. The house still contains some of the original furniture used by Hemingway when he lived there for almost a decade in the 1930s. His cats’ descendants (and there are a lot of them) still wander the grounds and gardens. Because of his affinity for cats with extra toes, many of them are six-toed cats. (Writers are ridiculous people.) Admission to the Hemingway House is $14 and includes a guided tour.

Another 10 minutes on foot and you’ll be at the Southernmost Point of Florida and the United States. It’s just a quick stop, but it’s a geographical highlight and shouldn’t be missed. It’s just 90 miles from Cuba.

key west

Saturday Afternoon

When you’re ready for lunch, head over to Bien (known to almost everyone by its former name, Paseo). This is a hole in the wall with only counter service, but trust me you want to eat there. At Bien, you can get sandwiches or full plates of meat and rice. Order anything that has the Paseo marinade (not sure if the name of that changed too) and do not forget to get fire roasted corn. Whatever you do, get that corn.

After lunch, you can fill your afternoon with beach adventures. From the end of Duval Street, you can book jet skis, glass-bottom boat tours, snorkeling, and even boats. If something like this is a must-do, you should plan ahead to make sure you get to squeeze it in. Even afternoon snorkeling to the reefs begins fairly early around 12:30 pm.

Fort Zachary beach

You can also head to the other side of the island to the beach at Fort Zachary Taylor. There’s a fee to get into the park which varies depending on whether you walk or drive. Once inside, you can rent beach chairs, umbrellas, and snorkels. The beaches in the Keys are beautiful, but very rocky, which is why so many people opt for more active beach activities.

Saturday Night

You’ll want to get a good view of the sunset on Mallory Square which faces the Gulf. This might be a good time to stop for dinner if you can find a restaurant with an open table. The Schooner Wharf Bar is one of the popular restaurants that overlooks the water so you can get yourself some food and a Margarita and enjoy the sunset like you’re in a Jimmy Buffet song.

After dinner, kick off your night out at Better Than Sex. This decadent cocktail and dessert bar is one of the main reasons to go to Key West. It’s sexy. It’s sweet. It’s not to be missed.

key west better than sex

Another night in the Keys means another trip down Duval. There is no shortage of places to go, so you don’t have to feel like you’re repeating anything. To add a little color to your evening, I recommend the Bourbon Street Pub, which is one of the most popular gay nightlife spots in Key West. This place can be a bit much, at least it was during pride. I will always fondly remember my horrified friend realizing that a man next to her was rubbing one out while watching the male go-go dancers. But those are the stories that interesting lives are made of, so come, enjoy, and tell your friends!

If you want a more low-key evening, there are plenty of relaxed dive bars, like the nearby Green Parrot, which is just a few blocks away and often has live music.

Sunday

key west blue heaven

Your last day in Key West is all about food. Before leaving the island, you’ll need to have the best brunch in town at Blue Heaven. Though they serve breakfast every day, I recommend Blue Heaven on Sunday so you can get more varied brunch options. You can get a traditional breakfast or something more involved like the Blue Heaven Benedicts which can be made with beef tenderloin or lobster. I know, I’m dying just thinking about it. The outdoor oasis is full of chickens, which adds to the charm of it all.

After brunch and before embarking on the drive back, pass by Kermit’s Key West Key Lime Shoppe. Here you can get all sorts of goodies to take home including key lime cookies, whole pies, fudge, taffy, and other gifts. For yourself… obviously these delicious gifts are for yourself.


Get the GPS-guided version of this article on GPSmyCity here.

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