Key West in March

November through April is peak season for good reason. Temperatures hover in the 70s and 80s, humidity drops, and the trade winds keep things comfortable. But you'll pay peak prices — hotels double their rates and restaurants get crowded. December through March offers the best weather but brings the biggest crowds. Fantasy Fest in October turns the island into a week-long costume party, but it's not for families. The event draws 75,000 people to an island with 25,000 residents. May through October is hurricane season, which means cheaper hotels but also means rain, humidity, and the occasional evacuation order. June through August feels like living inside a sauna. But here's the upside — you'll have the beaches mostly to yourself, and locals are more relaxed when the tourist hordes thin out. Avoid Labor Day weekend and Spring Break unless you enjoy crowds and inflated prices.