San Gimignano in November

April through June and September through October offer the best weather without summer crowds. May is particularly lovely — wildflowers bloom in the countryside and temperatures hover around 70°F. Summer brings tour buses and heat that can make walking the cobblestones miserable. July and August see temperatures over 85°F with no shade in the main squares. But if you come in summer, visit early morning or late afternoon when the light is golden and the crowds thin out. Winter has its charm — fewer tourists and cozy restaurants with fireplaces — but many businesses close from November through March. The towers look dramatic against gray winter skies, and you might have Piazza della Cisterna to yourself. Just bundle up, as medieval stone buildings don't retain heat well.