Things to Do in Siena in October
October weather, activities, events & insider tips
October Weather in Siena
Is October Right for You?
Advantages
- Harvest season transforms the Tuscan countryside - vineyards around Siena are actively harvesting Sangiovese grapes through early October, and you can actually watch the process rather than just touring empty cellars. Many wineries offer vendemmia experiences where you pick grapes alongside workers, then crush them the traditional way. The landscape shifts from summer's golden brown to autumn amber, making those postcard views of Val d'Orcia even more dramatic.
- Comfortable walking temperatures throughout the day - those 19°C (67°F) afternoons are genuinely ideal for climbing Torre del Mangia's 400 steps or exploring Siena's contrade neighborhoods without the summer crowds melting on the pavement. Mornings start cool enough at 11°C (51°F) that you'll want a light layer, but by 11am you're in perfect sightseeing weather that lasts until sunset around 6:30pm.
- Post-Palio calm means locals have time for you again - the August Palio madness is over, September's recovery period has passed, and Sienese shopkeepers and restaurant owners are genuinely relaxed and chatty before the brief fall tourist bump. You'll get better service, longer conversations, and locals actually eating at the restaurants you're considering, which is always a good sign.
- White truffle season begins in late October - while Alba gets all the press, the Crete Senesi hills south of Siena produce exceptional tartufo bianco. By the last week of October, you'll find fresh truffles shaved over pappardelle at trattorias for 18-25 euros instead of the 35-45 euro prices you'd pay in peak winter season. The San Miniato truffle festival is just 90 km (56 miles) north if you want to go deep on fungi.
Considerations
- Rain shows up without much warning - those 10 rainy days in October tend to be scattered afternoon thunderstorms rather than all-day drizzle, but they can dump 20-30 mm (0.8-1.2 inches) in an hour and turn Siena's steep marble streets into slippery bowling alleys. The medieval city wasn't built with drainage in mind, so low-lying areas near Fontebranda can get properly waterlogged. Pack shoes with actual tread.
- Shorter daylight means compressed sightseeing windows - sunset around 6:30pm means many attractions close by 5pm or 5:30pm, giving you maybe 6-7 hours of practical touring time after a civilized breakfast. Museums like Santa Maria della Scala close at 7pm, but outdoor sites like the Duomo complex wrap up earlier. If you're used to long summer evenings in Italy, October feels abbreviated.
- Shoulder season confusion with opening hours - some restaurants and shops shift to winter schedules in October, others wait until November, and nobody agrees on when exactly this happens. That enoteca you read about might be randomly closed on Tuesday and Wednesday, or taking a two-week break before winter season starts. Always call ahead or have backup plans, especially in smaller towns like Montalcino or Pienza.
Best Activities in October
Chianti and Brunello Wine Harvest Experiences
October is literally harvest month in Tuscany's wine country, and vineyards within 30 km (19 miles) of Siena are picking Sangiovese grapes through the first two weeks. Unlike summer wine tours where you're just tasting in empty cellars, October lets you see fermentation tanks actively bubbling and smell that distinct yeasty sweetness of fresh must. The weather is perfect for cycling between wineries - cool mornings, mild afternoons, and those dramatic autumn light conditions photographers obsess over. Vineyards in Montalcino and the Chianti Classico zone are most active early October, while smaller producers around San Gimignano continue into late month.
Via Francigena Hiking Routes
The medieval pilgrimage route from Canterbury to Rome passes directly through Siena, and October weather is ideal for tackling sections without summer's brutal heat. The 32 km (20 mile) stretch from San Gimignano to Monteriggioni is particularly stunning in autumn when vine leaves turn copper and morning mist sits in the valleys. Temperatures in the high teens Celsius mean you can hike 5-6 hours comfortably, and those occasional rain showers actually make the cypress-lined paths more atmospheric rather than miserable. The route is well-marked with brown Via Francigena signs, and small towns every 8-10 km (5-6 miles) offer places to refuel.
Cooking Classes Focused on Autumn Ingredients
October brings porcini mushrooms, fresh chestnuts, and late-season zucchini flowers to Siena's markets, and cooking classes shift menus to reflect what's actually available. You'll learn to make pappardelle ai funghi porcini using mushrooms foraged that morning, or ribollita using cavolo nero that's just come into season. Classes typically run 9am-2pm or 4pm-9pm, starting at local markets where you'll select ingredients alongside your instructor. The cooler weather makes standing over a hot stove more pleasant than summer sessions, and you'll actually want to eat the rich, hearty dishes you're preparing.
Thermal Spa Towns Circuit
The hot springs around Bagno Vignoni and Rapolano Terme are especially appealing in October when morning temperatures dip to 11°C (51°F) and you can soak in 37-40°C (99-104°F) thermal pools while watching mist rise off the water. These aren't crowded summer scenes - you'll share the waters with Italian families and older couples doing thermal therapy treatments. Bagno Vignoni's main piazza IS a thermal pool, which is wonderfully surreal, and the free hot springs at Fosso Bianco just below the town let you test the waters before committing to spa entry fees. The 45 km (28 mile) drive from Siena through Val d'Orcia is spectacular in autumn light.
Contrade Neighborhood Walking Exploration
October is when you can actually explore Siena's 17 contrade districts without summer's crowds blocking the narrow streets. Each neighborhood has its own museum, fountain, and distinct identity that goes back centuries, and locals are around and willing to chat about their contrada's history and rivalry with neighboring districts. The Oca, Drago, and Lupa contrade museums keep irregular hours but are often open Saturday and Sunday afternoons. Walking the boundary markers between territories gives you a completely different understanding of how Siena actually functions versus the tourist version you see in Piazza del Campo.
Crete Senesi Landscape Photography Routes
The clay hills southeast of Siena turn incredible shades of amber and grey in October, and the lower angle autumn sun creates dramatic shadows across the rolling landscape between 7am-9am and 4pm-6pm. The famous lone cypresses and winding white roads photograph better now than summer when everything is bleached and hazy. Morning mist in the valleys adds atmosphere, and you'll have locations largely to yourself on weekdays. The circuit from Asciano through Leonina to San Giovanni d'Asso covers about 50 km (31 miles) of the most photogenic terrain, with multiple places to pull over and shoot.
October Events & Festivals
Vendemmia Wine Harvest Activities
Not a single festival but rather a month-long working harvest across the region. Throughout October, wineries around Siena open their doors for grape picking experiences, barrel tastings of last year's vintage, and harvest dinners. The actual work is happening, so you're seeing real production rather than staged demonstrations. Many agriturismos host weekend harvest celebrations with traditional grape stomping, live music, and multi-course meals featuring seasonal ingredients. The atmosphere is festive but authentic, focused on locals celebrating the year's work rather than performing for tourists.
Sagra del Tordo in Montalcino
This medieval festival in the last weekend of October celebrates the thrush hunting season with archery competitions between Montalcino's four quarters, flag throwing, and outdoor feasting on local game and Brunello wine. The archery tournament uses traditional crossbows, and the competition gets genuinely intense with neighborhood pride on the line. Food stalls serve pappardelle with wild boar ragu, roasted thrush, and ribollita, with Brunello flowing freely. It's more authentic than Siena's tourist-focused Palio events, partly because fewer international visitors make it to Montalcino in late October.