How do I get around Key West?

Key West measures about 4 miles east to west and 2 miles north to south. You can walk from the Southernmost Point buoy on Whitehead Street to Mallory Square in roughly 25 minutes, and that route passes most of what you came to see. The sidewalks along Duval Street get sticky with spilled daiquiris by mid-afternoon, and the humidity tends to hover around 80% year-round, so carry water even for a 10-minute errand. The Old Town grid is flat, the blocks are short, and street numbering runs consistently enough that you won't need GPS for most walks. After dark, the stretch between Truman Avenue and the waterfront stays well-lit and populated until about 1 a.m. North of Truman, the residential streets get quieter and dimmer, but you're never more than a 5-minute walk from a busy corridor.

A single-speed beach cruiser rents for $15-20 per day at shops along Simonton Street and near lower Duval. This might be the best $15 you'll spend in Key West. The island is dead flat, bike lanes run along most through-streets, and you can ride from the Ernest Hemingway House on Whitehead Street to Fort Zachary Taylor Historic State Park in about 8 minutes. Theft is the number-one property crime in Key West, and an unlocked cruiser on Duval Street will likely disappear in under an hour, so use the cable lock that comes with every rental even for a 5-minute stop. Electric scooter and moped rentals run $40-70 per day from outfits along North Roosevelt Boulevard. They're useful for reaching Smathers Beach or the neighborhoods east of White Street, but parking a moped on Duval during the evening is more trouble than the convenience.

The city runs a free bus called the Duval Loop, which circles between Mallory Square and the corner of South Street and Simonton roughly every 15 minutes from 6:30 a.m. to midnight. It's air-conditioned, which matters more than you think when the heat index hits 32°C in September. The Lower Keys Shuttle connects Key West to Marathon and Big Pine Key for $4 each way if you're staying up the chain. Uber and Lyft both operate on the island, but the driver pool is small. Wait times run 10-20 minutes during the day and longer after midnight. A ride from Key West International Airport to Duval Street runs about $12-15 on the app. Worth noting, taxis charge a flat $7 per person from the airport to Old Town, which might work out cheaper if you're solo. Pedicabs line up along Duval in the evening and charge $2-3 per block per person, negotiated before you climb in.

Do not rent a car unless you plan to drive up to Marathon or Key Largo for a day trip. Parking in Old Town costs $4 per hour at metered spots and $20-30 per day at the few garages. Street parking is restricted on most residential blocks, and the Key West police ticket on every expired meter. The one-way grid around Fleming and Southard Streets is narrow, the feral chickens cross without warning, and you will spend more time circling for a spot than you would walking. If you need wheels for a day trip up the Keys, rent from the airport location on South Roosevelt Boulevard and return it the same evening. That said, golf cart rentals run $150-200 per day and seem appealing but follow the same parking and traffic laws as cars. They're slow, exposed to afternoon rain, and cost 10 times a bicycle. A rented cruiser handles every destination on the island in under 30 minutes.