Ahoy, Key West!
Key West will forever be one of my favorite places on earth. The island city is a strange-but-wonderful weirdo tangle of the hippy tropics and the old south. Beautiful victorian homes tucked between palm trees, shoeless locals, and booze-filled tourists unexpectedly find a way to flow together. Key West is far from tame, but the hospitality is warm and welcoming, albeit a little wild. Your survival kit should include a pack of thank you notes and a bottle of Pedialyte.
I’ve been lucky to spend a number of holidays in Key West—my favorite time of year to visit because the cruise ship crowds thin a bit and there’s something so silly about Santa in the South Florida heat. Most recently, I visited for Christmas week with my mom and best friend Alissa. On a mutual mission to let our normal holiday anxieties melt away, we played in the sun, laughed until we cried, and did our best to not crash our rented beach cruisers. Here are our favorite finds.
Eat.
I’m allergic to seafood (ugh), so my dining recommendations are a bit limited because Key West lives for the fresh catch. Sorry, charlies.
Flaming Bouy. There are a few things that confuse me about this restaurant—the Star Wars decor and the a-little-bit-random menu—but the food is delicious and the staff, who will be your best friends in no time, are the kindest humans. In a word, The Bouy is endearing. You can tell this little place is owned by Key West lifers who adore welcoming their guests into their sweet space. It’s definitely a favorite for island regulars, so make a reservation if dining on the weekend. Map, Website.
Little Pearl. In my opinion, Little Pearl might be the best restaurant on the island. We love it so much we chose to have our Christmas Eve dinner here. This teensy restaurant is famed for super fresh seafood, to which I’m sadly allergic, but their whole menu is regional and thoughtful. For our holiday dinner, they had run out of the non-seafood main for me, but the chef offered to pull together a duck dish just for me from the ingredients he was saving for a special family meal. It was truly delicious and I still cannot believe how kind it was to make sure my night was special. Oh boy I love this place. Reservations absolutely necessary every night. Map, Website
Moondog Cafe and Bakery. The front porch of this little cafe is the best place for a hangover recovery brunch. The food is fresh, the coffee is strong, and they have lots of vegan and gluten free options. Bonus, most of the porch seats are in the shade so you can take things slow and watch the cruise ship families snap iPad photos as they battle their way into the Hemingway House. Salads are great, pastries are even better, fresh squeezed juices will truly save your life. Map, Website.
Drink.
While a boozy stroll down Duval Street should definitely be on your Key West to-do list—at least one frozen bev out of glowing cup strongly suggested—our favorite bars are off the island’s main drag.
General Horseplay. A newishcomer to Key West, this little cocktail bar is already becoming an island favorite. It was opened by a couple of veteran Key West bartenders and it’s clear they had an awesome vision for a unique space. The interior bar is cozy, interesting, and a perfect place to make new friends. The outside bar, which feels like your cool friend’s backyard, has space for darts and live music. The cocktail menu is a lot to take in—we had some absolute winners and some that needed a bit more balancing—but it’s a real treat to get away from the vodka Red Bull specials on Duvall. Plus, the bartenders were an absolute delight. Moral of the story, we found ourselves here twice in our five day visit and I would go back in a heartbeat. Map, Website.
Green Parrot Bar. I love this bar so much I almost don’t have the words to describe it. Here’s what you need to know about this beautiful old mess of a bar. Lots of locals, cheap drinks, free popcorn, live music, drunk dancing parents, brusque bartenders, open windows, cigarettes. Just go. Go now. Go in the afternoon. Go at the end of the night. Lean into how weird and wild it is. It’s the parrot, baby. Map, Website.
VIV Wine Bistro Alissa, mom, and I happened upon this sweet little spot when we got caught in a quick afternoon downpour (which you should know is pretty regular in the Keys). Wine is about the last thing I expected to drink during our trip, but VIV changed my mind. The owner is kind and knowledgable and was excited to help us find a wine we’d like based on our preferences. I’d suggest stopping here in the afternoon when you need a little break from the busy streets. VIV is in the heart of the Bahama Village neighborhood, which has a super-special vibe that’s so different than the rest of Key West, so make time to take a little walk around the surrounding streets too. Map, Website.
Visit.
Duval Street. If you’ve heard wild reports from Key West, they’ve probably been from Duval, a major street that spans the island north to south. Duval is home to multi-level bars, strange street performers, tons of restaurants and souvenir shops, and perhaps the best people watching on earth. Drinking on the streets of Key West isn’t technically legal—I believe the law allows open container, but doesn’t allow you to drink from it—but it’s pretty rare that the police are bothered unless you’re acting like a complete idiot. You’ll likely find yourself on Duval a number of times during your stay and the options can be overwhelming. if you’re not sure where to go, ask your friendly bartender for tips. Map
Key West Cemetery. This beautiful, calm place is one of my favorite spots in Key West. It’s tucked in the middle of residential neighborhood and is wonderfully calm compared to the mania of Duval Street. The cemetery’s history is fascinating, read this Atlas Obscura piece before you visit. When there, keep an eye out for the slapstick headstone engravings, roaming chickens, and resident iguanas! When you’re done visiting, spend an hour or two biking around the surrounding neighborhoods. Some of Key West’s most beautiful bungalows, tropical gardens, and tchotchke-filled porches can be found down the small side streets. Map
Mallory Square at sunset. At the north end of Duval Street, Mallory Square is tourist central—mostly because all of the cruise ship and hotel shuttles stop here. In my opinion, there is almost no reason to visit this square during the day unless you want to buy some tacky crap. But, as much as it pains me to say it, the sunsets here are worth enduring the Made In China tie dye and white girls with vacation cornrows. Almost every night, the sky lights up red and orange, and there’s something kind of cheeky and fun about cheering when the sun finally falls below the horizon. When the applause ends, scoot right out of there and go find a grownup drink. Map
Take Note.
Check the calendar. Before you visit, do a little research to see if there are any big events happening in Key West. Because the weather is wonderful year-round, the city hosts many festivals, including the famed Fantasy Fest. The city gets insane when a big event is on, so check first to make sure you’re up for the party.
Fly or ferry. Getting to Key West without driving from Miami can be a bit tricky because the airport is teensy and flights can be expensive. When planning your visit, take a peek at flights to/from Fort Myers, Florida as well because they may be more affordable. From Fort Myers you can take a beautiful and not-too-expensive Key West Express Ferry to get to Key West.
Keep it casual. As a New Yorker, it’s not always easy for me to let go of my liquid eyeliner and all-black outfits, but in Key West it feels like second nature. Jean shorts, t-shirts, sandals, and beach hair are the island’s uniform. Take advantage of the vibe and relax. I’d maybe pack may one nicer outfit if you’re headed out to dinner, but keep it casual as you’re adventuring. You’ll be more comfortable and, in my personal experience, the locals will be more likely to befriend you. This might be the one place where it’s better under than overdressed.
Rent a bike. Driving around Key West is truly not worth is because the city is so small and parking is a nightmare. Instead, rent a beach cruiser bike for the duration of your stay. There are rental shops all over the place and many hotels and airbnbs provide bikes for you. Helmet wearing isn’t very common around the island, but if you’re a nervous biker (or just want to be extra safe!) the bike shop should have one for you. Be careful if you’ve been drinking, I have seen cops ticket drunk bikers. Instead, lock it up for the night and take a taxi or a stroll.
