What's happening in Key West this week?

Old Town sees two kinds of crowd. On ship days, one to three cruise ships tie up at Mallory Square, Pier B and the Outer Mole, and their passengers fill Duval Street and Front Street from about 10am until the ships usually sail around 4pm. Check the Port of Key West schedule the night before and plan around it. On a ship day, be at the Ernest Hemingway House on Whitehead Street when the gate opens at 9am: the six-toed cats are still asleep on the porch chairs then, and the rooms smell of old pine and floor wax. At midday, go west to Fort Zachary Taylor Historic State Park. Its beach is coarse, broken coral, not soft sand, so water shoes are worth the $15, and the water off the fort's rock jetties is the clearest snorkeling you can reach on foot from Old Town. Head back to Duval after the ships leave.

Sunset Celebration at Mallory Square runs every night and starts about two hours before sundown, with tightrope walkers, steel drums, fire jugglers, and conch fritter stands frying through it all. Go once. It is packed and loud, and the good railing spots are gone by 6pm, so on your other nights, watch from the Sunset Pier behind Ocean Key Resort with a drink in hand, a 3-minute walk away. After dark, skip the cover-band bars on lower Duval and go to the Green Parrot Bar at Whitehead and Southard, a sticky-floored corner room that has long run free early-evening sets on Fridays and Saturdays and stays open into the small hours. Capt. Tony's Saloon on Greene Street is worth one beer, since it sits on the original Sloppy Joe's site. The 700 and 800 blocks of upper Duval are the LGBTQ+ strip, where Bourbon St. Pub and 801 Bourbon Bar have drag shows most nights.

Shoulder season in Key West comes with a catch: Fantasy Fest, the island's adults-only costume festival, takes over Old Town for about ten days each autumn, and Old Town hotel rates can roughly double during that stretch. Expect body paint, street parties, and noise past 2am. Key West scores 6.2/10 for family friendliness (see the TTDI Family-Friendliness Index), and Fantasy Fest week drags that number down, so families with kids should pick another week. The live events list on this page has the confirmed dates. During hurricane season, a tropical storm watch is still possible, so book refundable and check the National Hurricane Center each morning. The latest evening reading was clear at 27.7°C with 70% humidity, which feels like a warm, damp towel by 1pm. Showers tend to roll in mid-afternoon and clear within 20 minutes.

Most Key West sights open seven days a week, so you don't need to plan around a closed Monday. Plan around the heat. From 1pm to 4pm, the Harry S. Truman Little White House is your best choice: it runs guided tours only, the rooms are cold, and the guides tell the poker-table stories well. The Mel Fisher Maritime Heritage Museum on Greene Street is cool inside too, and it holds Spanish galleon silver from the 1622 Atocha wreck. Skip the midday line at the Southernmost Point buoy at Whitehead and South Streets, which can run 30 to 45 minutes, and go at 7:30am instead. A few menu notes for a first visit: conch fritters are chewy, mild sea-snail dumplings, and real key lime pie is pale yellow, never green. Kermit's on Elizabeth Street sells the tart, graham-crust version. On Sunday, Blue Heaven in Bahama Village has brunch queues by 9am, with roosters pecking around the gravel courtyard. Old Town is about 2 miles across, so rent a bike and leave the car.