Mile Marker 0 — the southernmost town in the continental US, end of the road.
Photo: Radomianin · CC BY-SA 4.0 · via Wikimedia Commons
Key West is the end of the line in the best way — the last island on the Overseas Highway, where US-1 runs out at Mile Marker 0 and the continental US simply stops. Drive the 113 miles down from the mainland, island-hopping a chain of bridges over impossibly blue water, and you arrive somewhere that feels more Caribbean than Florida: pastel conch houses, gumbo-limbo trees, roosters in the street, and a pace set by the heat and the tides.
The old town packs a lot into a few walkable blocks. Snap the obligatory photo at the Southernmost Point Buoy (just 90 miles to Cuba), tour Ernest Hemingway's 1851 home and its colony of six-toed cats, and wander Duval Street's lanes of galleries, cigar shops, and verandahed inns. Every evening the whole island drifts toward Mallory Square for the Sunset Celebration — buskers, jugglers, and a crowd applauding the sun into the Gulf.
The water is the real headline. Fort Zachary Taylor anchors the best beach and a Civil War-era fort, and the Historic Seaport launches the ferry 70 miles west to Fort Jefferson at Dry Tortugas National Park. Give it two or three days and let the island slow you down.
The candy-striped concrete buoy marking the southernmost point in the continental US — '90 Miles to Cuba' painted on the side. One of the most photographed spots in Florida, and a near-mandatory road-trip selfie at the end of US-1.
Insider tipLines for the photo can run long midday; come at sunrise for an empty marker and soft light.
Plan a trip to this spot →Key West's nightly ritual — an open-air arts festival that fills the harbor-front plaza every evening as the sun drops into the Gulf. Street performers, jugglers, food carts, and crafts, all building to a round of applause for the sunset itself.
Insider tipArrive 45 minutes before sundown to claim a railing spot. For a calmer view, walk over to the Fort Zachary Taylor beach or book a sunset sail out of the Historic Seaport instead of fighting the square's crowd.
Plan a trip to this spot →The 1851 Spanish-colonial home where Hemingway lived and wrote through the 1930s, producing some of his best-known work. The grounds hold the island's first in-ground pool and roughly 60 polydactyl (six-toed) cats descended from the author's own.
Insider tipThe included guided tour is genuinely good and runs every 20–30 minutes. Go early before the heat and the tour buses, and the cats are friendliest in the cooler morning hours.
Plan a trip to this spot →The mile-long main drag running gulf-to-Atlantic, lined with galleries, cigar rollers, ice-cream and key lime shops, and the verandahed inns and conch houses that define Key West architecture. The side streets off Duval are where the quiet, leafy charm lives.
Insider tipWalk it gulf to Atlantic in the cool of morning, then explore the gingerbread homes on the residential lanes a block or two off it. A bike or the hop-on Conch Tour Train covers the spread-out sights without the parking headache.
Plan a trip to this spot →A pre-Civil War brick fort and National Historic Landmark fronting the island's best swimming beach — calm, clear water, shaded picnic groves of Australian pines, and snorkeling right off the rocks. The quietest corner of a busy island.
Insider tipThere's a small per-vehicle state-park entrance fee, and the rocky bottom rewards water shoes. Rent a chair and umbrella on site, and it doubles as a low-key, crowd-free spot to watch the sunset.
Plan a trip to this spot →Island food here means fresh-off-the-boat seafood, the conch-and-key-lime classics, and the Cuban cooking that came north from Havana 90 miles away. Eat where the locals eat and skip the tourist-trap stretch of Duval.
Conch fritters are the local rite of passage — crisp, peppery, loaded with conch at spots like El Siboney and the casual seafood shacks around town. Pair them with fresh hogfish, grouper, or stone crab in season, and finish with a slice of tart, custardy key lime pie (a chocolate-dipped frozen slice on a stick is the walk-around version).
Local tipKey lime pie should be pale yellow, never green — green dye is the tell of a tourist version. Stone crab claws are at their best mid-October through spring.
Key West's Cuban roots run deep. El Siboney has served hearty, no-frills Cuban plates — ropa vieja, roast pork, pressed Cuban sandwiches — since 1984 at honest prices. Around town you'll find Caribbean-leaning kitchens leaning on mango, jerk spice, and the morning ritual of strong Cuban coffee at a sidewalk window.
Local tipGrab a café con leche and a guava pastry from a coffee window for breakfast — it's the most local way to start a Key West morning, and cheaper than any cafe.
For atmosphere, Blue Heaven serves famously good breakfasts and seafood in a ramshackle courtyard where roosters roam the sandy floor and live music plays. The Historic Seaport's dockside kitchens put fresh catch and conch baskets right on the water, watching the shrimp boats and ferries come and go.
Local tipBlue Heaven doesn't take reservations and the morning wait can run long — put your name in, then wander the gallery streets nearby until your table's ready.
Key West is hot, humid, and subtropical year-round, moderated by the surrounding water — winter highs in the mid-70s°F make December–April the dream season. Summer highs sit near 90°F with heavy humidity, and the rainiest, stormiest stretch is August through October, overlapping Atlantic hurricane season.
Where you sleep is mostly about whether you want walkable Old Town charm or a beach-resort base — and how you'll deal with the island's notoriously tight, expensive parking.
The classic Key West stay is a converted conch house or historic inn in Old Town — tin roofs, gingerbread trim, tropical courtyards with a pool, often within walking distance of Duval, Mallory Square, and the Seaport. Locally owned guesthouses and the small historic-inn collections are the signature option.
Booking tipStaying in Old Town lets you park the car and leave it — you can reach almost everything on foot, bike, or scooter, dodging the island's worst headache: finding a parking spot.
A handful of full-service resorts sit on the island's south Atlantic shore, including the few hotels with private beach access — think Casa Marina and The Reach near the Southernmost Point. You trade walk-everywhere convenience for a pool, sand, and resort amenities.
Booking tipThese are a 10–15 minute walk or quick bike ride from Duval — close enough to dip into the action, far enough to escape it. Watch for resort fees and paid parking on top of the room rate.
Key West rooms are pricey and book out well ahead in winter high season; rates ease in summer when the heat thins the crowds. Standard chain hotels cluster near the start of the island (around US-1's arrival) and on the busier highway end, away from the historic core.
Booking tipLock in winter and holiday dates months out, and read the parking fine print — many Old Town inns offer just a space or two, and a downtown room without parking can mean paying for a public lot all week.
Should I drive down or fly in?
The drive is the experience. The Overseas Highway runs about 113 miles from the mainland down the Keys, crossing 42 bridges (including the Seven Mile Bridge) over turquoise water — plan 3.5 to 4 hours from Miami without stops, and far longer if you stop to swim and eat along the way. If you're short on time, Key West International Airport (EYW) has direct flights from several US cities, and you genuinely don't need a car once you're on the island.
How do I get around once I'm there?
Old Town is small and flat, so most visitors ditch the car. Walking covers the core; bikes, scooters, and electric golf carts are the local way to range a little wider and are easy to rent by the day. The Conch Tour Train and the hop-on Old Town Trolley loop the main sights with narration. Parking is scarce and expensive, so if you drove down, tuck the car at your inn and leave it.
How do I visit Dry Tortugas National Park?
Dry Tortugas — a remote cluster of islands with the massive 19th-century Fort Jefferson, crystal water, and great snorkeling — sits 70 miles west of Key West and is reachable only by boat or seaplane. The Yankee Freedom ferry runs a daily day trip from the Historic Seaport: roughly 8 a.m. departure, 3 p.m. return, with breakfast, lunch, snorkel gear, and the fort tour included. It sells out weeks ahead in season, so book early.
How many days do I need?
Two to three days is the sweet spot. One full day covers Old Town — Hemingway's home, the Southernmost Point, Duval, Fort Zachary Taylor, and the Mallory Square sunset — and a second lets you slow down on the water with a snorkel trip, a sail, or the kayak-and-paddle mangroves. Add a third day if you want the all-day Dry Tortugas excursion, which eats a full day on its own.
When's the cheapest and quietest time to come?
Late summer and early fall (roughly August into October) bring the lowest rates and thinnest crowds — but that's also the hottest, most humid stretch and the heart of hurricane season, so weather is a gamble. The shoulder months of May and November are a good compromise: still warm and far cheaper than the December–April peak, with lower odds of a washout.
Is it kid- and family-friendly?
Yes, away from the late-night Duval scene. Fort Zachary Taylor's calm beach and historic fort, the butterfly conservatory, the Eco-Discovery Center, the shipwreck and aquarium attractions, and the Conch Train all play well with kids. Daytime Key West is relaxed and walkable; just plan family outings for daytime and morning hours, when the island is at its most easygoing.
Pick your vehicle, line up the stops on the way in and out, and carry the whole route in your pocket.
