Can I leave the airport on a layover in Key West?

The four-hour floor works out like this. Allow 20 minutes from gate to curb, because EYW has one small concourse and a checked-through bag never slows you down. The cab rank outside arrivals charges roughly $20 to $25 to Duval Street, while Uber and Lyft pick up from the marked curb and get you into Old Town in 10 to 15 minutes along South Roosevelt Boulevard, with the salt flats and the smell of low tide on your left. The return is the part that catches people out. EYW runs a single TSA checkpoint, and on a busy Saturday between January and April the line can pass 30 minutes, so we plan to be back inside 75 minutes before departure. On anything under four hours, stay in the terminal. The food there is thin, but the trade-winds on the curbside benches outside arrivals are a better use of 90 spare minutes than half-seeing Whitehead Street at a jog.

Our two-hour loop starts at the striped concrete buoy at Whitehead and South streets. At midday the photo queue there runs 20 to 40 minutes, so take your shot from the sidewalk beside it and move on. Five blocks north, Hemingway House at 907 Whitehead Street is the stop we would protect if you can keep only one, with guided tours running often, tile floors that stay cool underfoot, and the six-toed cats dozing in the shade wherever they please. The Truman Little White House, a 10-minute walk further up near Truman Annex, admits visitors by guided tour only, so check the next start time before you commit. Fort Zachary Taylor is the better swim, but its beach is coarse coral rubble, and the walk in from the gate takes longer than it looks. We would leave the fort for layovers of six hours or more.

Solo diners get a break here: most Key West kitchens seat walk-ins at the bar, so you never run into a booking system built for two. Pepe's Cafe on Caroline Street has served breakfast since 1909, and its counter fills with locals by 8 a.m. Blue Heaven on Thomas Street in Bahama Village serves its key lime pie under a meringue piled 3 inches high, with roosters scratching under the outdoor tables, and the open-air bar seats there feel the most sociable to us. Key West scores 7.2/10 for solo-traveler safety (see the TTDI Solo-Safety Index). In our experience the main danger is traffic, not crime: rented scooters and bikes weave through Duval Street with little warning, and after 10 p.m. the 100 to 300 blocks of lower Duval fill with loud, drunk bar crowds. Bahama Village is fine by day and goes dark and quiet after nightfall, so after sunset keep to the lit stretches of Duval and Whitehead and order your ride from a busy corner.

Pack for the heat first. At 7 p.m. on 19 October it was still 27.7°C with 70% humidity under a clear sky, and the pavement on Whitehead Street holds that warmth well after dark, so carry a litre of water and a hat. Hurricane season runs to 30 November, and storms can cancel the small regional jets that serve EYW at short notice, which makes a travel policy with trip-delay cover, such as World Nomads, matter more here than at a big hub. We could not find a staffed left-luggage desk at EYW, so leave the airport with a daypack and nothing you would mind carrying in the heat. With seven hours or more, Mallory Square's free sunset gathering on the waterfront is worth staying for: the fire-eaters and the smell of fried conch fritters make it easy to fall into conversation with strangers, and Old Town is still a short ride from your gate when it ends.