What should I avoid in Key West?

The Southernmost Point buoy at Whitehead and South streets is the biggest time sink in Key West. By 11am the line tends to run 30 to 45 minutes with no shade, and the concrete throws heat back at your ankles. Go before 8am, when the corner is quiet enough to hear waves slap the seawall, or skip the photo. The true southern tip of the island sits on fenced Navy land to the west anyway. Duval Street is the other first-day mistake. It runs about 1.25 miles from the Gulf to the Atlantic, and the lower blocks around Sloppy Joe's at 201 Duval smell of spilled beer and fryer oil by noon. Bars there can pour until 4am, and the bass from the cover bands carries through hotel walls. We'd walk lower Duval once, around 9pm, then sleep closer to the Atlantic end, or in the Truman Annex streets near the Harry S. Truman Little White House.

Lower Duval's T-shirt shops have a long record of quoting one price for custom printing and ringing up another, often charged per letter, with no refunds, so buy nothing there that isn't tagged. The sidewalk booths marked as visitor information on Duval and Front Street tend to be timeshare desks, and the cheap sunset-cruise tickets cost you a 90-minute sales pitch. Food has its own traps. Real key lime pie is pale yellow and tart enough to make your jaw tighten, so a green slice anywhere in Key West is food coloring. Kermit's on Elizabeth Street and Blue Heaven on Thomas Street in Bahama Village both serve the yellow kind. Conch fritters are fried dough balls with minced sea snail, chewy and mild, and many Duval kitchens seem to serve them from the freezer. We'd order Key West pink shrimp or a hogfish sandwich at B.O.'s Fish Wagon on Caroline Street or Eaton Street Seafood Market at 801 Eaton instead.

Don't rent a car at Key West International Airport. Old Town is roughly 2 miles long by 1 mile wide, the taxi ride in takes about 10 minutes, and street meters run around $5 an hour when you can find one. The free Duval Loop bus and a rented bicycle cover every sight on the first-timer list. Scooters look fun on Whitehead Street, but first-time riders, wet pavement and loose chickens send visitors to Lower Keys Medical Center every week. We'd also skip the day trip from Miami: US 1 is 160 miles each way and usually 3.5 to 4 hours, with a 35 mph night limit through the Key deer zone on Big Pine Key. Beaches are the last letdown. Smathers Beach on South Roosevelt Boulevard is trucked-in sand, and summer sargassum there can smell like rotten eggs, but Fort Zachary Taylor Historic State Park at the end of Southard Street has the clearest water on the island. The bottom is sharp coral rock, so pack water shoes.

Avoid midday sightseeing for most of the year. At 7am on October 13, the reading was already 26.4°C with 85% humidity, which felt like 29°C before the sun cleared the rooftops on Whitehead Street. Book the Ernest Hemingway House for its 9am opening, when the rooms are still cool and the six-toed cats are awake. Atlantic hurricane season runs from June 1 to November 30, so buy refundable rates for any trip in that window. Fantasy Fest takes over Duval Street for about 10 days in late October with body paint, adult costumes and hotel prices that can double, so families should pick different dates; TTDI rates Key West 6.2/10 for family friendliness (see the TTDI Family-Friendliness Index). Cruise ship days crowd Mallory Square and Front Street from roughly 10am to 4pm. The Mallory Square sunset celebration is still worth it once the ships leave, and the jugglers start about an hour before sundown.