What should I avoid in Key West?

The single biggest first-timer mistake is renting a car. Old Town is about 1 mile across, a 20-minute walk from one side to the other, and the one-way grid will loop you past the same conch fritter stand three times before you find a spot. Private lots near Mallory Square charge $30-40 for a full day. A rented bicycle from one of the shops on Eaton Street gets you from Fort Zachary Taylor at the southwest corner to Higgs Beach on the south shore in about 8 minutes. The city bus covers the full island loop for $2 a ride.

Duval Street between Front and Southard is where first-timers lose the most money. Any spot with a photo menu and someone working the sidewalk charges $22-28 for fish tacos that cost about $14 at Garbo's Grill, a food truck on Greene Street near the corner of Thomas. The conch fritters at those tourist-facing spots taste like deep-fried breading with a faint rumor of shellfish. Walk two blocks off Duval to El Siboney on Catherine Street for a Cuban roast pork plate at $16. The dining room fills with garlic and slow-cooked oregano, and the portions could feed two. Cruise ship days make the congestion worse. When 3 or 4 vessels dock at the Navy Mole, 8,000-plus passengers flood Old Town by 9am. The line at the Southernmost Point buoy, the concrete marker on Whitehead Street installed in 1983, can stretch past 45 minutes in full sun. That said, port schedules post nightly, and a ship-free morning cuts that wait to under 5 minutes.

Key West sits at latitude 24°N. The UV index hits 11-12 on a clear summer afternoon, and the sea breeze tricks you into thinking the heat is mild until you're lobster-red at dinner. Reef-safe sunscreen is the only type the dive shops along N. Roosevelt Boulevard stock. If you're visiting between August and October, watch the National Hurricane Center forecasts. The only road out is U.S. Route 1, and an evacuation to Florida City takes 4 or more hours in bumper-to-bumper traffic. At dusk on still evenings, no-see-ums, tiny biting midges, swarm along the shoreline near Smathers Beach and White Street Pier. A steady wind keeps them away. A calm night without DEET means itchy welts by morning. The air right now is 27.6°C at 80% humidity, and it feels like 32°C the moment you step off a porch.

The sunset crowd at Mallory Square draws hundreds every evening, and a few of the street performers are worth stopping for. But the $8 frozen drinks from the waterfront carts taste like sugar water with a splash of rum, and the 'free' rum-tasting rooms on Front Street are sales funnels for $45 bottles of flavored spirit you'll find at any grocery for $20. For the water, skip the $85 jet ski tours that run the same 2-mile loop around Fleming Key. A kayak rental from Lazy Dog on Stock Island costs about $45 and puts you into the mangrove channels, where the water turns clear green and a nurse shark might drift through 3 feet below you. The Conch Tour Train runs $39 per adult for a circuit a 40-minute walk covers better. Worth noting, Key West scores 7.2 out of 10 for solo-traveler safety (see the TTDI Solo-Safety Index), so walking Old Town after dark is low-risk, and you hear the roosters and the live sets from bars like The Green Parrot on Whitehead.