48 Hours in Key West

There is nothing like a weekend getaway down to the Florida Keys, and this time we are heading down for a “Southernmost” adventure in Key West!

Famous for warm weather, tiki bars, live music, more tiki bars, and great food, Key West is a Florida vacationer’s paradise with a nearly endless number of options for places to stay, things to do, and excellent restaurants.

Assuming that you’ve never been down to The Conch Republic before, here is how we suggest spending your 48-hour weekend in Key West. 

Where to Stay?

If you are looking for the ultimate Key West hotel experience, it’s hard to beat the first-class service at Margaritaville Beach House Key West. Located right across the street from famous Smathers Beach, this island-style beach resort offers all of the amenities you need for a perfect weekend getaway. 

Another great place to say, especially for anyone looking to keep the Key West nightlife at arm’s length, is The Perry Hotel located just up U.S. 1 on Stock Island. This charming boutique hotel sits right on an active marina, and anyone looking to relax could enjoy an entire weekend without ever leaving this property. 

Of course, the heart of Key West is always going to be on Duval Street, which is surrounded by a fantastic selection of rental units. Whether you prefer one of the big online rental sites or one of the local guys like Vacation Homes of Key West, you really can’t go wrong with any rental in Key West. 

Day One: Oysters, Trolley Tours, Filets, Sunsets

One of the best things about Key West is that the tourist destinations and local hangouts all kind of blend together, so for our first stop on the island, we are heading to Pepe’s, which is a great spot to kick back and enjoy a couple of beers with a plate of oysters. 

Once you are adequately fed and relaxed, it’s time to get to know the island aboard the Old Town Trolley. This tour features 13 stops that make up some of the best attractions Key West has to offer, and you’ll have the option to hop on or off the trolley at any of them. (Make sure that you hop off for the must-have Key West photo at the Southernmost Point!)

When making dinner reservations for your first night in Key West, the first option on your list should be The Flaming Buoy Filet Co. This fantastic little restaurant towards the northern end of Duval Street offers the perfect combination of casual Key West atmosphere with delicious upscale cuisine. 

Depending on when your dinner reservations fall, you will also want to make sure you get up to Mallory Square to watch an iconic Key West sunset. 

It isn’t really a first night in Key West without a trip to Sloppy Joe’s, so if you are looking for a few more cocktails following dinner, just make the quick stroll down Duval to this iconic bar that is ALWAYS open late. 

Day Two: Beach, Fried Chicken, Hemingway, Tapas, Drag Shows

Heading to the beach is the best way to kick off any day in Key West, so that is what we’re doing on our first full day in town. If you are staying at Margaritaville, your best bet will be to stay right at Smathers Beach, and if you are staying closer to Duval, you might want to check out Higgs Beach instead since it’s a bit closer. 

After enjoying the morning sun, it’s time to take a quick stroll to the closest Dion’s Quik Chik for some of the most mind-blowing fried chicken you’ve ever had. Don’t let the gas station atmosphere fool you. This is world-class chicken!

Going back to the beach for the afternoon is certainly an option, but if you want to fit as much as possible into this weekend adventure, another choice would be to head over to the Hemingway House. Daily tours here run almost nonstop. Make sure to give yourself enough time to appreciate both the history and the cats!

For dinner on our second night in Key West, we’re making reservations for a fabulous tapas meal at Santiago’s Bodega. Small plates are the name of the game here, so come hungry and plan on ordering a wide variety of dishes to share!

If you’re feeling extra adventurous after dinner, you might want to check out one of the drag shows along Duval Street. If that’s a little risqué for your taste, another option is to simply grab a couple of frozen drinks and stroll up to Mallory Square, where there is almost always something fun happening. 

Day Three: Shipwrecks, Crepes, Shopping on Duval

On the off-chance that it happens to rain on your last day in town, or at any other point during your stay, the Shipwreck Treasure museum up by Mallory Square is a great indoor experience that is perfect for a bit of morning fun. 

Another great way to spend your last morning in Key West is to enjoy a relaxing breakfast or brunch at La Creperie French Cafe, located just off Duval Street. This genuine French creperie is considered one of the very best restaurants in a town full of great restaurants, so don’t let your diet get in the way of a delicious crepe. 

Regardless of what you do or where you eat on your last morning in town, there is no doubt that you are going to want to take one last stroll down Duval Street before heading back to reality. That makes this the perfect time to explore the different boutique shops that line both sides of the street. 

Just like that, we’ve spent 48 hours in beautiful Key West, and to be honest, we’ve only just barely scratched the surface of everything there is to see and do here. But don’t worry, because you can start planning your next trip back to this Florida Keys paradise as soon as you like!