Old Havana in May

November through April gives you the best weather — dry days around 75°F and cool evenings perfect for walking cobblestone streets. December and January get busy with European tourists escaping winter, but the energy is infectious. March hits the sweet spot. Fewer crowds than peak season but still dry weather. Plus you'll catch the Festival Internacional del Nuevo Cine Latinoamericano if you're into film. Avoid May through October unless you love humidity and afternoon thunderstorms. Hurricane season runs June through November, though direct hits on Havana are rare. Here's what nobody tells you: winter evenings can get surprisingly cool. Bring a light jacket for those late-night walks along the Malecón. And regardless of season, pack comfortable walking shoes. Those colonial cobblestones look romantic but murder your feet after eight hours of exploration. One insider tip: visit during Semana Santa (Holy Week) for incredible processions through the streets, but book accommodation months ahead. The entire city transforms into an outdoor cathedral.