Havana in September

November through April gives you perfect weather – 75-80°F with low humidity and minimal rain. December and January are peak season, so expect higher casa particular rates and more crowds in Old Havana. February hits the sweet spot with great weather and fewer tourists. March brings spring break energy but manageable crowds. April starts getting warmer but still comfortable for walking around all day. May through October means hurricane season, oppressive humidity, and afternoon thunderstorms. But you'll pay 30% less for accommodation and have restaurants to yourself. Hurricane season peaks August through October – risky but potentially rewarding if storms stay away. The rainy season doesn't mean all-day downpours, just intense afternoon showers that cool things down.