How to Spend the Perfect Weekend in Key West

There’s something magical waiting at the very end of the Overseas Highway. Four hours south of Miami, where the warm water turns impossibly turquoise blue and time seems to loosen its grip, you’ll find Key West, a funky, free-spirited island town that has a way of welcoming you exactly as you are. After more than a decade and over two dozen trips there, I still feel it every time I arrive: a sense of calm, curiosity, and joy that’s impossible to rush and even harder to leave.

Part of what makes Key West so special is its people. From the moment you check in, you’re met with the warmest, most down-to-earth hospitality in South Florida. Hotel and resort staff don’t just work here, they care here, greeting you with genuine smiles and an ease that instantly puts you at peace. This is a place where you can truly relax. Put away your makeup, slip on your trusty pair of flip-flops, and head to dinner exactly as you are. No one is judging. No one is rushing. You’re officially on island time. (There’s a reason why Jimmy Buffett loved it so much; it’s always five o’clock somewhere here.)

Your days can be as leisurely or adventurous as you want them to be. Sleep in and enjoy a slow morning coffee, all while watching a local rooster ruffle up his feathers before his morning performance, or hop on a bike and wander the island around the Truman Annex without a plan, because here, no one notices and no one minds. Locals and visitors alike move with a shared sense of friendliness and openness, whether they’re gathered around live music at Sloppy Joe’s (check out the 11 Best Bars in Key West), chatting around the bar at Hog’s Breath Saloon, walking around Duval Street with a piña colada from Sunset Pier, or simply passing each other on the street. It’s that rare kind of place where everyone feels welcome and effortlessly at home.

And then there are the hotels, each one its own slice of paradise. From the waterfront charm of Ocean Key Resort and the historic elegance of La Concha to the laid-back escape of Parrot Key and the quaint beauty of Marquesa Hotel, staying in Key West is a treat in itself. Add in seafood that’s impossibly fresh, like the wonderful Florida lobster and shrimp Benedicts at Blue Heaven or Banana Cafe, sunsets that stop you in your tracks near Mallory Square, and a hospitality scene fueled by genuine kindness, and you’ll understand why this island keeps calling me back. After years of sun-soaked visits and more key lime pie than I can count (make sure to snag a chocolate-dipped key lime pie on a stick from Kermitt’s!), here’s how to spend the perfect weekend in Key West: where to stay, what to eat, where to drink, and how to savor every magical moment in the Southernmost City.

How to Plan Your Perfect Friday-Sunday Itinerary

Whether you land at Key West International Airport on Friday morning or drive down from South Florida by noon, make sure to have the perfect two-to three-day itinerary mapped out beforehand. This way, you can truly move as you please throughout the island. However, you truly can’t go wrong in the Conch Republic (you can’t have a bad meal or drink here, even if you just walk in and eat at the bar).

Despite this, some fine-dining spots require reservations up to a week in advance, so make sure to book ahead. On the flip side, make sure you don’t get too exhausted after a day of sipping delicious cocktails along Duval… you may miss your 6:30 p.m. dinner reservation and wake up to a nice charge on your account the next day (been there, done that). Once you have a reservation secured for Friday and Saturday night, the rest of your itinerary can be moved around and followed—or not! Key West is all about going where the warm ocean breeze takes you. Enjoy every moment and don’t wear any uncomfortable shoes… you’ll be walking around all weekend! A comfy pair of sneakers, sandals, or flip-flops is ideal. Also, bring a hat and sunscreen. Even in the cooler months, that Conch Republic sun will get you, and you’ll want to drink and dine outside at most restaurants. I’m so jealous you’re going!

Where to Have Lunch

B.O.’s Fish Wagon: B.O.’s Fish Wagon is delightfully wonky and no-frills in the best way possible, serving some of the best grouper and cracked conch I’ve ever had in an old-school, counter-order spot that proves incredible Key West seafood doesn’t need fancy prices or fuss. 801 Caroline St., Key West; 305-294-9272; bosfishwagon.com.

Conch Republic Seafood Company: Yes, it’s a bit touristy, but for good reason — this lively waterfront seaport spot is one of my favorites for food and drinks, thanks to incredibly fresh seafood straight from the boats, standout dishes like conch ceviche and grilled Key West pink shrimp, spectacular views, and a fun, friendly staff that keeps the vibe relaxed and welcoming. 631 Greene St., Key West; 305-294-4403; conchrepublicseafood.com.

DJ’s Clam Shack: Beloved by locals, myself, and even Food Network’s Guy Fieri, DJ’s Clam Shack is a can’t-miss Key West stop for insanely good coconut shrimp and one of the best Maine lobster rolls in town, all served in a totally outdoor, beachy, slightly grungy shack that feels perfectly Conch Republic. 629 Duval St., Key West; 305-294-0102; djsclamshack.com.

Eaton Street Seafood Market: Founded in 2007, Eaton Street Seafood Market is a beloved Key West staple for its deep commitment to local fishermen and ultra-fresh catch, serving everything from pink shrimp and yellowtail snapper to grouper and stone crab, and it’s truly one of those places you can’t leave the island without visiting. 801 Eaton St., Key West; 305-295-3474; kwseafood.com.

Half Shell Raw Bar: This is a legendary, old-school Key West seafood spot where harborfront views, pelicans overhead, and award-winning classics like conch ceviche and broiled garlic oysters come together for a laid-back meal that feels like pure island paradise. 231 Margaret St., Key West; 305-294-7496; halfshellrawbar.com.

The Key West Lobster Shack: This has been my go-to spot for delicious Key West lobster rolls piled high with fresh and buttery Key West lobster and a queeze of Key West Key lime…to die for. 507 South St., Key West; 305-741-7149; lobstershackkw.com.

Where to Get a Drink and Bar Hop

General Horseplay: For a break from Duval Street’s chaos, General Horseplay is one of the island’s only true craft cocktail bars, offering a moody speakeasy vibe, some of the best espresso martinis in Key West, inventive drinks made with local ingredients, quirky Robin Williams–lined walls, live music out back, and a dangerously fun “2 Cents” dice-roll happy hour that makes it easy to lose track of time. 423 Caroline St., Key West; 305-741-7599; generalhorseplay.com.

Hog’s Breath Saloon: Hog’s Breath Saloon is a true Key West rite of passage, delivering nonstop live music, cold drinks, great seafood, and pure island energy on Duval Street, all wrapped up in its legendary motto, “Hog’s breath is better than no breath at all.” 400 Front St., Key West; 305-296-4222; hogsbreath.com/keywest.

Irish Kevin’s: Irish Kevin’s is one of Key West’s most unforgettable Duval Street bars, serving nonstop live music, sing-along chaos, cold drinks, and pure island fun from morning to late night, with legendary shots like the Cinnamon Toast Crunch Shot making it a must-stop for anyone ready to fully embrace the party. 211 Duval St., Key West; 305-292-1262; irishkevins.com.

Mary Ellen’s: Owned by the team behind General Horseplay, Mary Ellen’s Bar & Restaurant is a beloved Key West indoor dive just off Duval Street where cold beer, loud music, comfort food classics, unpredictable fun, and even dog-friendly bar nights come together (and yes, you should order the Frozen Irish Cream with Oreos). 420 Appelrouth Ln., Key West; 305-294-7750; maryellensbar.com.

Sloppy Joe’s: This legendary bar is the beating heart of Key West, a nearly century-old Duval Street legend beloved for its Hemingway lore, nonstop live music, strong drinks, and timeless island magic that keeps crowds coming back generation after generation. 201 Duval St., Key West; 305-294-5717; sloppyjoes.com.

Willie T’s: Willie T’s is one of Key West’s most electric bars, known for its block-away-audible live music, walls plastered with signed dollar bills, nonstop energy, and legendary margaritas that are literally bigger than your head. 525 Duval St., Key West; 305-294-7674; williets.com.