October-April: What Key West lacks in weather during its peak season, it more than makes up for with its nightlife scene. Even the otherwise empty seats will be the butt of all attention during the months from October-April. Pack accordingly and if you don’t want to end up with the worst seats and rooms everywhere you go, book well in advance- even if it’s months. If you’re visiting Key West towards the end of the year, pack warm clothes! As the year begins, so does clear skies and sunny days, so plan your visit wisely.
May-August: The onset of May brings with it a transition of weather of off-season rates and fewer crowds. Although a few places might still be crowded and you might think twice before going there but it’s not nearly as bad as the peak season. A lot of events like the 4th of July celebration and the Cuban American Heritage Festival are just some of the things to look forward to.