Key West

Key West is a small coral island city — roughly 4 miles long and 2 miles wide — sitting at the very tip of the Florida Keys, 90 miles (145 km) north of Cuba and connected to the US mainland by the legendary Overseas Highway (US 1). It carries the twin distinctions of being the southernmost city in the contiguous United States and one of the country's most idiosyncratic places: a former sponging and cigar-manufacturing town turned literary haunt (Ernest Hemingway lived here for a decade; Tennessee Williams was a regular) turned raucously popular sun-and-rum tourism destination. The city retains genuine character beneath the cruise-ship crowds — Victorian Conch-style wooden houses painted in candy colours, a serious fishing culture, an LGBTQ+ heritage going back decades, and a laid-back ethos locals call the "Key West way." The Conch Republic spirit — born in 1982 when Key West briefly declared symbolic independence from the United States to protest a Border Patrol roadblock — is celebrated with genuine pride every April.

The island divides roughly into Old Town (the historic western end, where most attractions, restaurants, and guesthouses cluster around Duval Street and Whitehead Street), Midtown, and New Town (the commercial eastern end near the airport and US 1). Mallory Square, at the northwestern tip, is the cultural heart of sunsets; the Bight marina area is the working waterfront. The pace is intentionally unhurried. Most visitors walk or cycle — the island is compact enough that a bicycle covers everything.

Key West has a true tropical monsoon climate, which makes it the mildest and technically the driest city in Florida despite a pronounced wet season. November through April is the dry season: plenty of sunshine, temperatures ranging from the mid-60s°F (around 19°C) at night to the upper 70s°F (around 26°C) by day, and very little rain. This is peak season and prices spike accordingly. May through October is the wet season, with daily showers (typically in the early morning, unlike mainland Florida), high humidity, and summer highs in the 90s°F (32–33°C) with a heat index frequently reaching 100°F (38°C) or above. Hurricane season runs June through November; the most active months are August and September. Key West is the only city in the lower 48 states to have never recorded a frost or snowfall, kept mild year-round by the nearby Gulf Stream. For value and manageable weather, late April–May and October–early November are the sweet spots.

By Plane

Key West International Airport (EYW) is at 3491 S Roosevelt Blvd (FL-A1A), about 3.9 miles (6.3 km) southeast of Old Town. Airlines serving Key West directly include American Airlines and American Eagle (connections from Charlotte, Chicago-O'Hare, Miami, New York LaGuardia, Washington Reagan), Delta Connection (Atlanta, New York LaGuardia), United and United Express (Chicago-O'Hare, Houston Intercontinental, Newark, Washington Dulles), and Allegiant (Asheville, Cincinnati, Indianapolis, Orlando-Sanford, Pittsburgh, St Petersburg FL). Fares into EYW tend to run higher than into larger Florida airports. A popular alternative is to fly into Miami International Airport (MIA) or Fort Lauderdale-Hollywood International Airport (FLL) — both roughly 160 miles (257 km) northeast — rent a car, and drive the Overseas Highway in 3–3.5 hours. Keys Shuttle (+1-888-765-9997) offers shared door-to-door van service from both Miami-area airports to Key West hotels; advance booking is required. Car rental at EYW is available from Avis, Budget, Dollar, Hertz, and Thrifty on-site, and from Alamo, Enterprise, and National via free airport shuttle; a car is unnecessary once in Key West but useful for getting there.

By Car / Road

The Overseas Highway (US 1) is the only road connection from the Florida mainland to Key West — a stunning, slightly absurd drive across 42 bridges spanning the open ocean. From Miami International Airport: take LeJeune Road south to I-836 west, then follow the Florida Turnpike south to its terminus at US 1 in Florida City, then follow US 1 southwest all the way to the end — approximately 160 miles (257 km), 3 to 3.5 hours without stops. From Fort Lauderdale: similar time via I-95 south to the Turnpike. Traffic on the two-lane Overseas Highway can be slow in peak season; the drive is scenic but there is no alternative route. Parking in Key West is expensive and spaces are tight — a car is largely unnecessary once you arrive. Paid public parking lots are available near the historic district; Old Town guesthouses often lack parking. Greyhound (3439 S Roosevelt Blvd, in front of the airport; +1-305-296-9072) runs two daily departures from Miami, stopping at Key Largo, Islamorada, Marathon, and Big Pine Key; journey time is approximately 4.5 hours and one-way fares start from around $30. Miami Info Tours (+1-305-894-6409) and Miami to Key West Bus (908 Caroline St; +1-305-423-9045) offer coach services from Miami Beach and Downtown Miami. The Lower Keys Shuttle, operated by Key West Transit, provides nine daily trips between Key West (MM 0) and Marathon (MM 53.5) for $4 each way, connecting at Marathon to Miami-Dade bus route 301 (the Dade/Monroe Express, $2.65 each way) for onward service to Florida City and eventually the Miami Metrorail.

By sea, Key West Express (100 Grinnell St; +1-239-463-5733) runs daily high-speed passenger ferries from Fort Myers Beach and Marco Island (approximately 3.5 hours each way), docking at the Key West Bight Ferry Terminal. Cruise ships dock at Mallory Square Dock, Pier B (Westin), or the Navy Mole; over half a million passengers arrive by cruise each year.

Key West's Old Town is extremely walkable — most sights, restaurants, and bars are within a 15-minute walk of each other. Cycling is the preferred local transport: rental shops are everywhere in Old Town, with rates around $15–25 per day for a single-speed beach cruiser. The flat terrain makes it easy. The Conch Train (yellow-and-green diesel tractor pulling open-air cars) and the Old Town Trolley offer narrated 90-minute loop tours of the island's sights — useful for orientation on arrival, with the trolley offering hop-on/hop-off privileges at about a dozen stops. Fares for both run around $35–40 for adults. Key West Transit operates local bus routes across the island. Taxis and rideshares (Uber and Lyft both operate here) fill gaps; fares within the island are modest. Rental scooters and electric bicycles are also widely available. Driving your own car around Old Town is inadvisable — streets are narrow, one-way, and parking is scarce and costly. The island is small enough that even New Town is only 10–15 minutes from Old Town by bicycle.

Mallory Square — Every evening the open-air waterfront plaza hosts the Sunset Celebration, a free street performance festival that draws jugglers, tightrope walkers, psychics, and musicians. Vendors sell food, drinks, and crafts. Arrive 30–45 minutes before sunset to get a good spot; the crowd disperses once the sun goes down.

Ernest Hemingway Home and Museum — 907 Whitehead St. The Spanish Colonial-style house where Hemingway lived from 1931 to 1940 and wrote A Farewell to Arms, To Have and Have Not, and For Whom the Bell Tolls. Now home to approximately 60 polydactyl (six-toed) cats, descendants of Hemingway's own. Open daily 9AM–5PM; admission around $18 for adults.

Harry S. Truman Little White House — 111 Front St. The modest Key West naval station building that served as Truman's winter White House for 175 working days across 11 visits. Guided tours run throughout the day; admission around $22 for adults.

Fort Zachary Taylor Historic State Park — End of Southard St. A Civil War-era brick fortification now encircled by the best beach in Key West — a small but genuinely swimmable stretch of clear water with minimal seaweed, a concession stand, and good snorkeling off the rocks. Admission is a few dollars per person for the beach; fort tours are included.

Key West Lighthouse and Keeper's Quarters Museum — 938 Whitehead St, directly across from the Hemingway House. Climb the 88 iron steps for a panoramic view of the island. Open daily; admission around $15.

The Key West Butterfly and Nature Conservatory — 1316 Duval St. A glass-enclosed habitat with 50-plus butterfly species, tropical birds, and flowering plants — a surprisingly peaceful escape from Duval Street. Open daily; admission around $15.

Duval Street — The main commercial artery running from the Gulf to the Atlantic (locals call walking its full length a "Duval Crawl"). The street is a mix of T-shirt shops, bars, restaurants, and live music venues. Worth strolling, at least once.

Key West Cemetery — Margaret St and Angela St. A compact but fascinating 19th-century cemetery with above-ground vaults (the water table is too high to bury below ground), famously irreverent epitaphs, and the graves of sailors, wreckers, and Cuban cigar workers.

Dry Tortugas National Park — 70 miles (113 km) west of Key West, accessible only by boat or seaplane. The centerpiece is the massive, unfinished Civil War fort of Fort Jefferson on Garden Key — one of the most dramatic and least-visited national monuments in the country, surrounded by pristine coral reefs and nesting seabirds. Day trips via the Yankee Freedom ferry (approximately $200 per adult round-trip, including park fee) leave from the Key West ferry terminal and take about 2.5 hours each way. The seaplane option (Key West Seaplane Adventures) is faster and more expensive.

Snorkeling and diving — Key West sits atop the Florida Reef, the only living coral barrier reef in the continental United States and the third-largest in the world. Dozens of dive operators offer half-day reef trips from the Bight marina; expect to pay $45–70 for a snorkel trip, $90–150 for a two-tank dive. Wreck diving on the 524-foot USNS Vandenberg (intentionally sunk in 2009 as an artificial reef, one of the world's largest diveable wrecks) is a standout.

Deep-sea and backcountry fishing — Key West has a large commercial and sport-fishing fleet. Charter boats for offshore fishing (mahi-mahi, tuna, sailfish) and backcountry/flats fishing (tarpon, permit, bonefish — world-class fly-fishing territory) leave from the Bight marina and A&B Marina. Half-day shared charters start around $75–100 per person; private charters run $400–900 per half day depending on boat and target species. Tarpon fishing in the spring migration is legendary.

Kayaking and paddleboarding — The shallow backcountry on the Gulf side is ideal for guided kayak tours through mangrove tunnels and tidal channels; tours run 2–3 hours and cost around $50–70 per person. Stand-up paddleboard rentals are widely available.

The Conch Republic Independence Celebration — Held annually in late April, this week-long festival commemorates the 1982 symbolic secession with parades, a mock naval battle in the harbor, costume contests, and general Key West absurdity. The largest event of its kind on the island.

Duval Crawl — Key West has one of the highest concentrations of bars per capita in the United States. The classic activity is an unhurried evening crawl from one end of Duval Street to the other, stopping at Captain Tony's Saloon (the original Sloppy Joe's that Hemingway actually drank at), Sloppy Joe's Bar (the current famous one), and the garden-style Green Parrot Bar (at the Whitehead end, beloved by locals).

Dolphin-watching and sunset sailing — Numerous sailboats and catamarans operate sunset cruises from the Bight marina and City Marina, with prices from around $50–80 per person including drinks. Dolphin-watching and glass-bottom boat tours are also popular.

Fantasy Fest — The city's largest annual event, held in late October. A 10-day festival culminating in a large adults-oriented costume parade on Duval Street. Book accommodation well in advance and expect significantly elevated prices.

Southernmost Point Buoy — The large red, yellow, and black concrete buoy at the foot of Whitehead St marks the southernmost point in the continental US (90 miles from Cuba, per the marker). It's a popular photo stop with a usually long queue.

Key West's food scene punches above the island's size, driven by exceptionally fresh seafood and strong Cuban and Caribbean influences from its geographic and historical position. The signature dishes are stone crab claws (in season October 15–May 15), conch fritters and conch chowder (a thin, tomato-based Florida-style chowder, different from New England's cream version), Florida spiny lobster (in season August through March), yellowtail snapper, and the genuine Key West pink shrimp, smaller and sweeter than Gulf varieties.

Budget

• B.O.'s Fish Wagon — 801 Caroline St. An outdoor fish shack that is exactly what it looks like — mismatched chairs, license plates nailed to wooden walls, and excellent fried fish sandwiches and conch fritters at very fair prices. A Key West original. Cash only.
• El Siboney — 900 Catherine St. A Cuban neighborhood restaurant far enough from Duval to avoid the tourist tax. Ropa vieja, black beans and rice, Cuban sandwiches pressed to order, and cafecito served in tiny cups. Modest prices; long a local staple.

Mid-range

• Garbo's Grill — William St at Greene St (food truck). A permanently parked food truck turned local institution, serving Korean BBQ tacos, fish tacos with mango slaw, and a short menu executed with precision. Lines form quickly around lunch and early evening.
• Alonzo's Oyster Bar — 700 Front St, at the A&B Marina. A casual waterfront seafood restaurant with fresh oysters, stone crab (in season), and daily fish specials. Good for a relaxed lunch or early dinner with harbor views.

Upscale

• Louie's Backyard — 700 Waddell Ave. The benchmark upscale restaurant in Key West, housed in a Victorian waterfront property with a multi-level deck over the Atlantic. The menu is ambitious New American with strong seafood; the AfterDeck bar below is one of the best sunset cocktail spots on the island. Mains typically $35–55.
• Michaels Restaurant — 532 Margaret St. A white-tablecloth steakhouse with an extensive wine list — an anomaly in Key West and a popular choice for a formal dinner. Known for prime beef and live piano.

Vegetarian options exist at most mid-range and upscale restaurants but are limited at seafood-focused spots; Cuban restaurants typically have vegetable side dishes but are not vegetarian-focused.

Key West is unambiguously a drinking town. The local specialty is the Key West Sunset Ale (from the Islamorada Beer Company, widely available) and a range of craft beers brewed on or near the island. The signature cocktail is the frozen daiquiri, dispensed in slushie machines from windows on Duval Street (legal to drink while walking). Rum drinks of all stripes dominate bar menus, influenced by the city's proximity to the Caribbean; the Rum Runner (a sweet, fruity rum cocktail invented at the Holiday Isle Resort in Islamorada) is ubiquitous.

Captain Tony's Saloon — 428 Greene St. The original location of Sloppy Joe's bar where Hemingway drank; now run independently, with genuine history and a relatively local crowd. A skull-and-bones flag, a hanging tree through the roof, and a wall papered in business cards.

Sloppy Joe's Bar — 201 Duval St. Loud, touristy, and unavoidable. The famous bar name was moved to this Duval Street location in 1937; Hemingway initially refused to follow. Live music seven days a week.

Green Parrot Bar — 601 Whitehead St. Key West's oldest bar (open since 1890), a beloved dive beloved by locals and travelers who've found their way off Duval. Pool tables, pinball machines, live music most nights, and an outdoor deck. A genuinely great bar.

The Rum Bar at The Speakeasy Inn — 1117 Duval St. Quieter and more civilized than most of the Duval strip, with an excellent rum selection and a shaded porch.

Tap water in Key West is safe to drink and comes desalinated from the mainland via pipeline.

Key West accommodations range from historic guesthouses in Victorian Conch-style houses to full-service hotels. Old Town is the preferred base. Prices are consistently among the highest in Florida; book well in advance for peak season (December–April) and festival periods (Fantasy Fest, Hemingway Days, Conch Republic celebrations).

Budget

• Hostelling International Key West — 718 South St. The only true hostel in Key West, a short walk from the Southernmost Point and Fort Zachary Taylor. Dormitory bunks and private rooms; a shaded garden and communal kitchen. Rates from approximately $40–60 per dorm bunk in shoulder season, higher in peak.
• Key West Youth Hostel & Seashell Motel — 718 South St (same property as HI Key West). Basic motel-style rooms attached to the hostel. Simple but clean; an honest budget option in an expensive city.

Mid-range

• The Southernmost House Hotel — 1400 Duval St. A Victorian mansion at the Atlantic end of Duval with a pool, small private beach access, and rooms that range from compact to spacious. Rates typically $200–350 per night in season.
• The Curry Mansion Inn — 511 Caroline St. A lovingly preserved 1899 Victorian mansion with 28 rooms, a pool, and a complementary breakfast. Central location; genuinely historic atmosphere. Rates from around $175–280.

Upscale / Heritage

• The Marker Waterfront Resort — 200 William St. A newer resort-style property on the harbor with a large pool, waterfront restaurant, and well-appointed rooms. Rates from $350–600+ in peak season.
• Parrot Key Hotel and Villas — 2801 N Roosevelt Blvd. A secluded waterfront property on the Gulf side with four pools, boat docking, and spacious villa-style rooms. Away from the Old Town crowds. Rates from $350–700 in peak season.
• Sunset Key Cottages (accessible by private launch from the Westin) — a private island 500 yards offshore with cottage-style lodging, no cars, and three restaurants. One of the most distinctive accommodation experiences in the Florida Keys. Rates from $700–1,500+ per night.

Key West's shopping is concentrated on Duval Street and the surrounding blocks of Old Town, though much of it leans toward T-shirts, shell-art, and tourist trinkets. More interesting options include:

Kino Sandals — 107 Fitzpatrick St. A Key West institution since 1966, handcrafting leather sandals on-site. Prices are reasonable and the sandals are genuinely made here — a far better souvenir than a snow globe. Open weekdays.

Key West Hand Print Fabrics and Fashions — 201 Simonton St. Locally designed and printed tropical fabrics, sarongs, and clothing; the print designs are distinctive and made on the premises.

The Key West Farmers Market (Clinton Square, near Mallory Square) runs on some weekend mornings with local honey, hot sauces, tropical fruit preserves, and produce. Local hot sauces and preserves (tamarind, guava) make excellent compact souvenirs.

Antiquing is a small but worthwhile pursuit; several antique shops operate on White Street and Truman Avenue. There is no meaningful bargaining culture in Key West — prices are fixed in almost all retail contexts.

Dry Tortugas National Park — 70 miles (113 km) west by boat or seaplane. The remotest unit of the National Park system in the lower 48 states: Fort Jefferson, pristine reefs, nesting sea turtles, and almost no crowds. A non-negotiable day trip if conditions allow.

Big Pine Key and the Lower Keys — 30 miles (48 km) northeast on US 1. The No Name Key bridge area is the best place to see the endangered Key deer — a miniature subspecies of white-tailed deer, barely knee-height. Blue Hole (a former quarry) on Big Pine attracts alligators and turtles. The Lower Keys backcountry fishing is exceptional.

Marathon — 50 miles (80 km) northeast on US 1. The mid-point of the Keys chain, with its own airport, the Turtle Hospital (a working sea turtle rehabilitation center open for tours), and the Museum of Natural History of the Florida Keys. The Seven Mile Bridge, just west of Marathon, is one of the most photographed stretches of road in the United States.

Islamorada — 85 miles (137 km) northeast. A Village of Islands renowned for offshore sport-fishing, excellent restaurants (including Morada Bay and Marker 88), and the Indian Key Historic State Park (accessible only by kayak or boat).

Miami — 160 miles (257 km) north on US 1. The natural gateway city for Key West arrivals, offering everything the Keys do not: world-class art museums, a vibrant international food scene, South Beach, nightlife, and direct international flight connections. Allow 3–3.5 hours driving time.

Cuba (Havana) — 90 miles (145 km) south. US regulations on travel to Cuba change periodically; at time of writing, direct commercial flights operate from Miami and Tampa, but no regular ferry or ferry service runs between Key West and Havana despite the minimal distance. Check current OFAC regulations before planning.