A reprieve from South Florida’s scorching summer sounds nice, right?
Every Florida local has a favorite Florida getaway. Some head north to float through natural springs, while others covet the roller coasters of Orlando. As for me? My favorite escape is Key West. With miles of ocean views, top-tier snorkeling and loads of historic charm, it’s not surprising this quirky little island paradise is more popular than ever. It’s idyllic, yes. But let’s be real: People come here to party, and the locals are no exception.
Key West’s bar scene is divey, the music is rowdy and restaurants are hit or miss. I know this from experience, having visited the Conch Republic over 10 times for spontaneous vacations, bachelorette parties, birthdays and, most recently, my honeymoon. In truth, I’d like to live here one day. Until then, I’ve lovingly assembled this comprehensive guide: an aspiring local’s handbook to Key West.
When to go
Key West sizzles in the summertime. Though it’s surrounded by water, there are times when you might wonder if this tiny town is landlocked—that’s how stifling the heat and humidity can be. But if you’re trying to experience the area like a local, we recommend planning a trip in the summer. Since it’s off-peak season, crowds are thinner, traffic isn’t as bad and the vibes (and prices) are way more chill.
Getting around
Biking is my favorite way to get around Key West, especially Old Town. You’ll cover way more ground than walking, thus increasing your chances of cool discoveries. Finding parking with cars and scooters is no fun (sometimes impossible). Plus it’s a gorgeous ride! I like renting from We Cycle. They’re reasonably priced with a friendly staff, and they offer complimentary bike pick-up and drop-off service.
Ocean adventures
Key West has so many water activities, it’s almost overwhelming. Deep sea fishing, scuba diving, snorkeling, kayak tours, sunset cruises, jet skis, parasailing, paddleboarding. You name it, Key West has it. Banana boats? Check. A giant inflatable water park that slides into the ocean? Yep, got that too.
Group charters are easy to find in Key West, though often overcrowded and somewhat less glamorous than what you might imagine. If you’re ballin’ on a budget, try haggling prices at the kiosks near Schooner Wharf. Sometimes you’ll score a deal and get on a pontoon that same day—and if you don’t, Schooner’s live music will keep you entertained.
For a more personalized experience on a private boat, consider charters that leave from nearby keys like Stock Island. (Pro tip: Stop for lunch at Hogfish Bar & Grill or Hurricane Hole Marina. Both are bomb, and they’ll cook your catch minutes after you’ve docked. It doesn’t get more local than that!)
Culture stops
Key West is only 4.2 square miles, but what it lacks in size it makes up for in character (and characters: Jimmy Buffet, Harry Truman and Judy Blume, to name a few). Random? Yes. Fascinating? Also yes!
Literary buffs may fancy a visit to The Hemingway Home, a residence-turned-museum filled with historic artifacts and the late author’s six-toed cats. The Key West Butterfly Conservatory is a lovely indoor garden that’s great for kids, and when you need a break from the sun. The Audubon House has winged creatures too, albeit drawn on paper by the famous Birds of America artist, John James Audobon.
For a bit of history with a side of day drinking, check out The Southernmost House, a Prohibition-era speakeasy that later hosted U.S. presidents like John F. Kennedy and Jimmy Carter. These days, it’s a boutique hotel with a chill waterfront cafe. Soak in the views with a bucket of beer and a slice of lobster pizza. (Pro tip: You’ll often find a frozen daiquiri shop set up down the block, and you’re nearby Louie’s Backyard, another oceanfront gem.)
There are plenty of other historic sites and niche museums worthy of your time. Many attractions offer ticket combos and group savings on their websites. Old-school coupon booklets are alive and well in Key West hotels, too. Find out what your hotel offers, and book directly through the business. You’ll get the best deal, and support local! Win-win.
Island dining
The best spots to eat in Key West are laid-back, sandal-friendly and very seafood-focused. That’s not to say you can’t find a decadent dinner in Key West, just don’t get your hopes up for caviar service or vinyl-spinning DJs. (We have enough of those in Miami, anyway.)
A majority of Key West’s best restaurants are in Old Town. Atlas Izakaya is an excellent date night spot for Japanese cuisine. The four-course tasting menu at Little Pearl is delightful, as is Azur, a Mediterranean restaurant and Andrew Zimmerman favorite. I love The Flaming Buoy, partially for its funky decor but mostly for the delicious food and super-friendly service. Hot Tin Roof, Santiago’s Bodega, Nine One Five and Blackfin Bistro are more great restaurants to have on your dinner radar.
On the hunt for a fat lobster roll? (And really, when are you not?) Check out DJ’s Clam Shack or the aptly-named (but unrelated) Lobster Shack, which serves not one, not two, but five different lobster rolls. Brunch and key lime pie at Blue Heaven are always a good idea, just like brunch dates at Moondog Cafe or The Breakfast Club, Too.
As for late-night eats, Mr. Z’s Philly cheesesteak comes highly recommended. Angelina’s Pizzeria will remind you of your college years. And in times of need, remember there’s always the hotdog stand outside of Rick’s.
I almost don’t want to tell you about Smoked, arguably the best barbeque in all of the Florida Keys and, according to their motto, “Home of the tender butts.” But, in the name of journalism! Tell them I sent you, bring me 48 bottles of their blackberry jalapeño sauce, and we’ll call it even.
Drink all day...
If day drinking were a sport, Key West would be an Olympian. Its reigning champ? Duval Street, of course. This 1.25-mile block has bar after bar, daiquiri shop after daiquiri shop. It’s like the Bourbon Street of Florida, right down to the Mardi Gras beads and barenaked body paint (look up “Fantasy Fest” and you’ll see what I mean).
Before you tackle the “Duval Crawl,” you must day party at Dante’s. Come on a Friday or Saturday to see the place in full swing. Partying with a big group? Get there early and hold down a table near the pool. Small groups, check out the Smallest Bar. When the mood strikes for cocktails and Jimmy Buffet covers, venture to Willie T’s or Hog’s Breath Saloon. And when it’s too hot for anything but ice, Flying Monkeys has the best frozen drinks to cool you down.
...Play all night
Have you ever walked into a bar and thought, “Woah, that musician needs to be famous”? Expect this reaction from just about every live act in Key West. From country singers to punk rock bands, Key West’s live music scene easily rivals Nashville’s. Yeah, I said it!! Sloppy Joe’s and Durty Harry’s are two of my go-to’s for aforementioned punk rock bands. Irish Kevin’s and Hank’s Hair of the Dog are also a blast. Sing along with locals at the Green Parrot, a Key West staple since 1890, or rock out to some face-melting guitar solos at General Horseplay.
Not to be outshined, Key West’s famous LGBTQ+ community puts on a show further down Duval. Party with drag queens at the 801, get into cheeky antics at Bourbon St. Pub, catch a live cabaret show at the Aquaplex, or head to 22&Co for a glitter-fueled bingo game.
Mix all of the above and you’ve got Rick’s, a multi-floor mecca of late-night debauchery. On floor one, live bands and pizza. Floor two is a dancehall with live DJs. And behind door number three? You’ll have to see for yourself. When all else fails and the bartender yells last call, just remember: there’s always the hotdog stand outside.
