Things to Do in Siena in September
September weather, activities, events & insider tips
September Weather in Siena
Is September Right for You?
Advantages
- Post-Palio calm means dramatically fewer crowds at major sites - you'll actually get quality time in the Duomo and Piazza del Campo without being swept along by tour groups. The difference from July and August is remarkable.
- Harvest season brings vendemmia (grape harvest) throughout Chianti - wineries open their doors for harvest tours, and restaurants feature seasonal menus with fresh porcini mushrooms, chestnuts, and new wine. This is when Tuscan cuisine is at its absolute peak.
- Weather sits in that perfect sweet spot - warm enough for outdoor dining and walking tours during the day (typically 20-25°C / 68-77°F), cool enough in evenings that you'll want a light sweater for those long dinners on terraces. No oppressive August heat.
- Accommodation prices drop by 30-40% compared to peak summer while the city retains its full energy - restaurants, shops, and attractions all operate normal hours, unlike the shoulder months when some places close for owner vacations.
Considerations
- September weather is genuinely unpredictable - you might get a full week of sunshine or three days of steady rain. Those 10 rainy days aren't evenly distributed, and when it rains in Siena's medieval streets, those steep stone staircases get slippery and drainage can be slow.
- Early September (first 10 days) still sees lingering summer crowds and higher prices from August overflow, particularly if Italian school holidays extend. You're better off targeting mid-to-late September for the full benefit.
- Mornings can be surprisingly cool at 14°C (57°F), especially in Siena's hilltop location at 322 m (1,056 ft) elevation - that temperature swing from afternoon to evening catches first-time visitors off guard if they've only packed for warm weather.
Best Activities in September
Chianti Wine Region Harvest Tours
September is vendemmia season - the grape harvest that defines the entire Tuscan calendar. Small wineries between Siena and Florence open for hands-on harvest experiences where you'll actually pick grapes, watch pressing, and taste must (pre-fermented juice). The countryside is active with workers, the light is golden, and temperatures in the 20-23°C (68-73°F) range make vineyard walking ideal. This isn't available any other time of year. Tours typically run 4-6 hours including lunch.
Siena Cathedral Complex Extended Tours
With reduced crowds in September, you can actually book the combined Opa Si Pass and spend 3-4 hours exploring the cathedral, Piccolomini Library, crypt, and baptistery without feeling rushed. The September light through the stained glass windows is spectacular in late afternoon (4-5pm). The Porta del Cielo (Gate of Heaven) rooftop tour is worth the climb - 77 m (253 ft) up - and in September's clear post-rain air, you'll see across the entire Val d'Orcia.
Val d'Orcia Countryside Cycling
September temperatures make this UNESCO landscape actually rideable - unlike July-August when the exposed hills hit 35°C (95°F). The famous cypress-lined roads between Pienza, Montalcino, and San Quirico are at their photogenic peak with golden wheat stubble and green vineyards. Routes typically cover 25-40 km (15-25 miles) with moderate hills. Morning rides (8am start) avoid afternoon heat and potential rain.
Siena Contrada Walking Tours
September is when locals reclaim their neighborhoods after summer tourism chaos. The 17 contrade (medieval districts) hold post-Palio social events, and you'll see residents gathering in their contrada museums and fountains. Guided walks through 4-5 contrade take 2-3 hours and explain the identity system that still defines Sienese life. You'll visit contrada museums (usually closed to casual tourists) and see the neighborhood dynamics that make Siena unique among Italian cities.
San Gimignano and Volterra Day Trips
These hill towns are 30-45 km (19-28 miles) from Siena and mobbed in summer, but September brings manageable crowds and that perfect warm-but-not-hot weather for climbing San Gimignano's medieval towers (54 m / 177 ft up narrow stairs). Volterra's Etruscan sites and alabaster workshops are best appreciated without tour bus hordes. The drive through Tuscan countryside in September light is worth the trip alone.
Porcini Mushroom Foraging and Cooking Classes
September rains trigger porcini season in Tuscan forests - those meaty mushrooms that dominate fall menus. Foraging experiences combine 2-3 hours of guided forest walking (locals know the spots) with cooking classes using your harvest. You'll learn to identify porcini, prepare traditional Tuscan mushroom dishes, and understand why this ingredient is so prized. This is deeply seasonal - only viable September through early November.
September Events & Festivals
Settembre Gastronomico
Throughout September, restaurants across Siena and surrounding towns host special tasting menus featuring seasonal ingredients - porcini mushrooms, chestnuts, new wine, wild boar. This isn't a single organized festival but rather a city-wide celebration of harvest season. Look for 'menu degustazione settembre' signs in restaurant windows. Multi-course meals typically run 35-50 euros.
Grape Harvest Festivals in Chianti Villages
Small villages throughout Chianti (Gaiole, Radda, Castellina) hold weekend sagre (food festivals) celebrating vendemmia. These are genuine local events with wine tastings, traditional music, and food stalls serving pici pasta, porchetta, and castagnaccio (chestnut cake). Dates vary by village and harvest timing, but most happen mid-to-late September. Entry is typically free, food and wine sold by ticket.