Drive the single road from Miami, about 160 miles, and it ends at Key West. It is the southernmost city in the continental US, a small island at the end of the Florida Keys with about 25,000 residents and a famously loose, independent streak, and it calls itself the Conch Republic. Most people come for Duval Street, the sunset celebration at Mallory Square, the Hemingway Home, the Southernmost Point buoy, and the reef for snorkeling and diving. A ferry or seaplane runs to Dry Tortugas National Park. Fantasy Fest in October is the wildest week of the year.
Living here is very expensive, with high rents, high home prices and insurance costs, though the market has cooled a little. Duval Street is rowdy late at night, with drunk driving and scooter accidents a real problem. Hurricane season brings evacuation risk with only one road out, and the sun and heat are intense.
Cities with a similar character, anywhere on the site.
Out of 10. Open any score to see how it’s worked out. “Data-based” scores come from published figures; “Hey! En Route estimate” scores are worked out from what we know about the city; “Hey! En Route rating” scores were set by our editors.
- Known as
- Southernmost City in the Continental US; Conch Republic; Cayo Hueso; Island City
- Founded
- Island claimed 1822 (settled by Americans, US flag planted March 1822); incorporated as a city 1828
- Languages
- English; Spanish widely spoken (about 22% Hispanic/Latino residents)
- Airports
- Key West International (EYW) about 3 miles east of Old Town, served by American, Delta, United and others; Marathon (MTH) about 50 miles northeast, general aviation; Miami Intl (MIA) about 160 miles (3.5 hour drive); Fort Lauderdale (FLL) about 190 miles
- Tipping
- Restaurants 18-20%; bars $1-2 per drink or 15-20%; charter boat crew 15-20%; taxis and rideshare 15-20%; hotel housekeeping $3-5 per night; bellhops $2-3 per bag; tour guides 15-20%
