Key West boasts beautiful weather and raucous good times year-round, and while it has the same seasonal ebbs and flows as the rest of the Florida Keys, its larger land mass and greater variety of things to do means that the differences between high and low aren’t quite as pronounced.
In general, the peak travel season stretches from October to April, around the end of spring break. These winter months have the most consistent weather, with temperatures hovering around 80 degrees—and also the biggest crowds, highest prices, and fewest last-minute options. The summer months from June to August also constitute a mini high season, especially among divers and watersports aficionados, for the calm seas and good water conditions.
The low season runs from August to October—also the hurricane season. Reduced crowds and lowered prices can be attributed to the steamy weather and windless doldrums (at least when tropical storms ain’t raging). The best times to find a combination of reduced crowds, lowered prices, and decent weather are the shoulder seasons from May to July and again from November to December.
Notable exceptions within the low and shoulder seasons include Key West’s numerous festivals, which predictably pack the island with revelers. Fantasy Fest, at the end of October, is an anything-goes Halloween party, and also one of the most packed weeks of the year, akin to Mardi Gras in New Orleans. Lobsterfest, in mid-August, marks the opening of lobster season—a time of year much anticipated among Conchs and mainland Floridians alike, and one that draws decent summer crowds to the end of U.S. 1.