Key West is 90 miles from Miami and feels like a different country. Three days is the right amount of time — long enough to find the places the tourists miss, short enough that you leave wanting more.
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Key West sits at the end of a 113-mile chain of islands connected by bridges and causeways, and it feels like it. The geography creates a certain psychology — you're at the end of the road, surrounded by water, and the pace of life reflects that. People slow down here in a way that doesn't happen in Miami.
We've been to Key West twice. The first time we did it wrong — too much time on Duval Street, too many overpriced drinks at tourist bars, not enough time in the neighborhoods that actually make the island interesting. The second time we did it right. This guide is based on what we learned.
Day 1: Arrive, Get Your Bearings, and Eat Something Real
The drive down the Overseas Highway is part of the experience. The Seven Mile Bridge is the highlight — you're driving over open ocean, water on both sides, and on a clear day you can see the curve of the earth. Pull off at Bahia Honda State Park on the way down if you have time. The beach there is one of the best in Florida.
When you arrive, resist the urge to go straight to Duval Street. Drop your bags, walk the Old Town grid, and get oriented. Key West's historic district is small enough to walk in an afternoon — the streets are lined with Victorian-era conch houses painted in pastels, with bougainvillea climbing the porches and chickens wandering the sidewalks. The chickens are not a gimmick. They're everywhere, they're protected by local ordinance, and they will absolutely walk into your restaurant if given the chance.
For your first meal, go to Blue Heaven in Bahama Village. It's the most famous restaurant in Key West for good reason — an open-air garden setting with roosters wandering between the tables, live music, and food that's genuinely good. The Caribbean BBQ shrimp is the move. The Sunday brunch draws lines down the block, but weekday lunch is manageable. If you're traveling with a dog, this is one of the most dog-friendly restaurants in the country — Split would be very comfortable here.
In the evening, walk to Mallory Square for the Sunset Celebration. This is a nightly street festival that starts about an hour before sunset and runs until dark — acrobats, musicians, artists, and food vendors, all gathered at the western tip of the island to watch the sun drop into the Gulf. It's touristy, yes, but it's also genuinely fun and the sunsets are extraordinary. Get there early for a good spot on the seawall.
Day 2: The Hemingway House, Fort Zachary Taylor, and the Best Key Lime Pie
Start the morning at the Ernest Hemingway Home and Museum on Whitehead Street. Hemingway lived here from 1931 to 1939 and wrote some of his most important work in the studio above the pool house. The house is preserved exactly as it was — his writing desk, his books, his hunting trophies. The 50-plus polydactyl cats that roam the property are descendants of his original cat, Snow White. The tour is worth the $16 admission.
After the Hemingway House, walk to the Southernmost Point buoy — the large red, black, and yellow marker at the corner of South and Whitehead Streets that marks the southernmost point in the continental United States (technically — there's a Navy base that's actually further south, but the buoy is the one people photograph). The line for photos can be long. Go early or late.
For lunch, find Kermit's Key West Key Lime Shoppe on Elizabeth Street. Key lime pie is Key West's signature dessert — a tart, dense custard made with local key limes in a graham cracker crust. Kermit's version is excellent and they do a frozen key lime pie on a stick that's perfect for walking around in the heat. The pie is made with real key limes, which are smaller and more aromatic than the Persian limes you find in grocery stores. It should be yellow, not green. If it's green, it's food coloring.
In the afternoon, go to Fort Zachary Taylor State Park on the southwest tip of the island. The fort itself is a Civil War-era fortification with an interesting history, but the real reason to go is the beach — the best beach in Key West, with clear water and a rocky bottom that makes for good snorkeling. Leashed dogs are allowed on the beach, which makes it one of the few beaches in the Keys where you can bring your dog. The entry fee is $6 per vehicle.
For dinner, walk away from the waterfront restaurants. The best food in Key West is not on the water — it's in the side streets of Old Town and Bahama Village. Harpoon Harry's near Duval Street does excellent seafood in a casual, no-fuss setting. The fish dip is a local staple — smoked fish, cream cheese, and crackers — and it's the right way to start a meal in the Keys.
Day 3: The Backcountry, Duval Street Done Right, and the Last Sunset
If you have any interest in fishing or kayaking, the third day is the time. The Key West backcountry — the shallow flats behind the island — is one of the best fishing destinations in the world. Tarpon, bonefish, and permit are the target species for fly fishing. Half-day kayak tours go into the mangrove channels and are accessible to beginners. The water is clear enough that you can see the bottom in eight feet of water.
If fishing isn't your thing, rent a bicycle. Key West is flat and compact — the whole island is about 4 miles by 2 miles — and a bike is the best way to see it. Ride out to the Key West Lighthouse on Whitehead Street (you can climb it for the view), through the quiet streets of the Casa Marina neighborhood, and out to the White Street Pier on the Atlantic side.
Duval Street is worth doing once, but do it on your own terms. The street runs the full width of the island from the Gulf to the Atlantic — locals call it the "world's longest bar" because of the density of bars along it. Sloppy Joe's is the famous one (Hemingway drank there, though the current location isn't the original), and it's worth a drink for the history. The live music starts early and goes late.
For the last evening, find a spot at Sunset Pier or back at Mallory Square and watch the sun go down one more time. Key West sunsets are genuinely different from anywhere else — the combination of the Gulf water, the humidity in the air, and the low horizon creates colors that last longer than they should. We've watched a lot of sunsets. Key West ones are in the top five.
What to Eat (The Short List)
Key lime pie is mandatory — Kermit's or the Blond Giraffe, both on Elizabeth Street. Conch fritters are the other Key West staple — crispy, golden, and best eaten at a waterfront shack rather than a sit-down restaurant. The stone crab claws (in season October through May) are worth the price if you're there at the right time. For breakfast, the Cuban coffee influence from Miami extends down the Keys — find a ventanita and order a café con leche.
Practical Notes
Key West is small enough that you don't need a car once you're there. Park your car at your accommodation and walk or rent a bike. Parking in Old Town is expensive and the streets are narrow.
The heat is real from May through October. The humidity is intense. Plan outdoor activities for the morning and evening, and find air conditioning in the middle of the day.
Accommodations range from budget guesthouses to high-end resorts. The best value is in the guesthouses and B&Bs in Old Town — they're often in historic buildings with character that the chain hotels don't have. Book well in advance for winter (November–April), which is peak season.
The drive back up the Overseas Highway is worth doing in the morning when the light is good. Stop at one of the roadside seafood shacks on Islamorada for lunch on the way back — the lobster rolls and fish sandwiches are excellent and much cheaper than anything you'll find in Key West itself.
We left Key West both times with the same feeling: we should have stayed longer. That's the best thing you can say about a place.
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Chris & Lori are the husband-and-wife team behind Bites & Borders — a travel and food blog built from real trips, real meals, and real opinions. Based in Virginia, they've explored the Mediterranean, the Caribbean, Hawaii, and beyond.
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