The Top Places You Need to Visit in the Florida Keys (Especially If You Have 48 Hours or Less)

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Best Places to Visit in the Florida Keys

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Despite being born and raised in Florida, I’d never been to the Keys—not until the summer of 2016. And within minutes of being there, I wondered how it took me so long to finally experience the laid-back vibe, plethora of (walkable!) beaches and restaurants and water so unbelievably crystal blue it seemed like someone had filtered the heck out of it.

For a few years, it was my annual getaway—just for 48 hours, sandwiched on a trip when I’d already be in Florida visiting family. Every time, it’s reinvigorating; the kind of place I dream of moving to while also realizing part of its magic is being a getaway from everything. (That and the fact that it’s pretty pricey to live there these days.)

The Best Places to Visit in the Florida Keys: Islamorada
Photos: Candace Braun Davison

Honestly, the Keys have everything you’d want from a tropical vacation, without having to fly halfway around the world. If you get the chance to go, GO. Don’t waste a second debating it. Don’t begrudge the long drive from Miami International Airport, or even the road trip from wherever you happen to live, if hopping on a plane isn’t your thing. Just go. You won’t be disappointed. (Key West’s airport is small but sufficient, though I’ve had more issues with flight cancellations there than anywhere else.)

So, just in case you’re considering a trip, here are my top places to visit, based on LBW’s Food, Fun & Fulfillment pillars.

mile 0 florida keys

My Ultimate 48-Hour Key West Itinerary

  • Day One:
    • Start the day with strong coffee and a breakfast Cubano at Cuban Coffee Queen. Their cold brew is fantastic and will wake you RIGHT UP, no matter how jet-lagged you are. Say hello to a wandering chicken or two.
    • Take a kayak tour or go paddle boarding. It’s worth having a tour guide and getting a lay of the island. I’ve really enjoyed trips with Lazy Dog Adventures; their tour guides have been friendly and knowledgable, and the routes aren’t too rigoroous, even if you’re new to kayaking. (Or you can rent a paddleboard, if that’s more your style.)
    • Savor Caribbean food alfresco at Kaya Island Eats for lunch. I really like the Cuban-Style Roast Pork and the Rasta Pasta.
    • Check out the Hemingway House for a dose of history, then try Hemingway’s daiquiri at Sloppy Joe’s or the Hemingway Distillery, if it’s still open by the time you leave. (It closes at 5, but plenty of places offer the drink, since it’s so renowned. Just be forewarned that it calls for twice the rum and no added sugar, and it includes grapefruit juice, making it a more citrusy, drier cocktail.)
    • Catch the sunset at Mallory Square (it’s one huge party, featuring live music and arts vendors and all kinds of fun), then wander downtown and see where the night takes you
  • Day Two:
    • There are plenty of great sit-down spots for breakfast, but if you have just two days, head to Koffie House for the vibes (and cold brew). Or go all out with a latte flight and a fat stack of pancakes. I’m an avocado toast person myself. If you’re feeling more indulgent, scroll down this list to find Glazed, home of the area’s best donuts.
    • The Key West Butterfly and Nature Conservatory is charming and delightful, so you could hit that up first thing or head straight to your car, because whatever you do, I highly recommend visiting Bahia Honda State Park. It feels like nature reclaimed the park and makes for an unforgettable beach day. (More details on that below, though note that it’ll take you about 45 minutes to an hour to get there, so you may want to pack lunch.)
    • If you stay in Key West, head to Garbo’s Grill for a casual lunch in their outdoor area. It’s renowned for being on Diners, Drive-Ins and Dives, and its creative riffs on tacos exceed the hype.
    • Grab a cocktail at General Horseplay, a quirky, lively and very fun bar in Key West. There are several Easter eggs that pay homage to Bill Murray—who inspired the name of the bar, when he said he cited “general horseplay” as the reason he’d sprained his wrist years ago. Some say he’s part owner, but I haven’t gotten official confirmation of that. Others say he pops up there randomly and whisper into guests’ ears, “no one will ever believe that you saw me here.” Folklore or real deal? Maybe you’ll need to visit and find out.
    • Dress up and enjoy a fancy dinner. Nine One Five has a fun fusion menu (the pappardelle with Wagyu bolognese is awesome, though I can make a meal out of the apps, like General Tso’s cauliflower and bacon-wrapped dates with bleu cheese dip). If you want something a little more laid-back, head to Blue Heaven for live music outdoors in a more enclosed, garden-like setting, with a mile-high Key Lime Pie that’s one of the best I’ve ever had.
    • If you skip dessert at the restaurant, go for a stroll until you find Mattheessen’s, where you can grab homemade ice cream, chocolate-dipped Key lime pie on a stick, fudge or a massive, half-pound cookie. You’re on vacation, after all.

Where to Find the Best Key Lime Pie in the Keys

I’ve tried several slices over the years, and I have to give it to the two mainstays: Kermit’s for a classic (or chocolate-dipped) slice; Blue Heaven if you want something topped with a fluffy, light meringue to balance out the tart lime flavor.

key west mural
Fact: I have never passed a mural I didn’t want to take a picture of, especially when it looks like an old postcard. It is what it is.

Other Great Things to Do While You’re in the Keys (Especially If You Have More than 2 Days)

FUN:

Bahia Honda State Park

Bahia Honda State Park
This park/beach will set you back about $8 per car, but it’s so worth it. The beaches are pristine, and the land seems almost untouched by time. The abandoned bridge to nowhere gives the whole area a Jurassic Park vibe. It’s picture-perfect — and worth an afternoon.

The Southernmost Point in the U.S.

The Southernmost Point in the U.S.
C’mon, you’ve got to do some cheesy, touristy stuff to mark the occasion, like posing at Mile Marker 0. Head there early in the morning to avoid long lines, or just take a pic next to the statue of the man blowing a conch shell like a horn, with the beacon in the background. It’s just as cool.

Key West Candle & Bath Co.

My crafters and candle makers will appreciate this charming shop. Visiting their Whitehead Street store is on my bucket list for my next trip after finding their candles at a store downtown. I love how the brand embodies the spirit of Key West.

FOOD:

The Ultimate Places to Visit in the Keys - Glazed Doughnuts in Key West

El Meson de Pepe
Cuban food so good you’ll eat yourself into a food coma. Order the Ropa Vieja (shredded beef simmered in a red wine sauce with peppers and onions), and plantains. So. Good.

Glazed Donuts
Gourmet doughnuts and cold brew better than any you’ll find from a chain or diner. There are plenty of island-inspired flavors, like Key Lime Pie, Pineapple Upside-Down Cake, and Peach Blessed Doussant (doughnut-croissant).

Kermit’s Key Lime Pie

Everybody will tell you that Kermit’s has the best Key Lime Pie, and if you’re looking for a custardy, tart classic, you’re right. It’s absolutely worth visiting, even if it’s so well-known that some roll their eyes at it. (Personally, I prefer to order a slice dipped in dark chocolate to offset the tangy flavor, but that’s just me.)

FULFILLMENT:

Hemingway House - what to see while you're in Key West
Photo: Candace Braun Davison

The Hemingway House
Tour the writer’s Key West home, pet his six-toed cats, dream of writing the next great American novel in a loft overlooking a pool.

What You Must See in Islamorada
Photo: Candace Braun Davison

Paddleboard Yoga
Even if you’re completely un-athletic (ahem, me), you can rock stand-up paddling. It just takes a little balance. NBD. Once you feel confident paddling around, take things to the next level with a local yoga class atop a board. (Lazy Dog also offers classes for this, though I haven’t taken theirs. A friend hosted a session over boards we rented, and it was enough to make me wish I could do it every week.)

Best Places to Check Out in the Florida Keys
Photo: Candace Braun Davison

Take a picture with Betsey the Lobster, a 30-foot-tall statue outside of Rain Barrel Village in Islamorada, on your way out of the Keys. And do some local shopping at the village, while you’re at it. It’s a quick detour, and a fun one.


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Editor’s Note: This article was originally published on September 2016. It has since been updated and expanded, based on several trips since then.

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