Fall in Tuscany: Olive Oil, Truffles, and Hill Towns Without the Crowds
Tuscany is one of those places that feels different in fall. The light gets softer, the crowds clear out, and the entire region starts to revolve around food, wine, and seasonal traditions. From olive oil pressing in Chianti to truffle hunting in San Miniato, this is the time of year when Tuscany shows off its roots.
Chianti: Fresh Pressed and Full Flavor
Fall is olive oil season in Chianti. The new harvest is bold, green, and nothing like what you get at the supermarket. Whether you’re touring a large estate or visiting a small farm, tastings are everywhere this time of year. You’ll dip fresh bread in oil that was pressed that week and leave with a new understanding of why Italians take their olive oil so seriously. Not to mention the wine!!
Chianti is also an easy day trip from Florence, with roads that wind through vineyards, medieval towns, and forested hills just starting to turn gold.
Montalcino: Vines, Hills, and Brunello
Montalcino in fall is about more than wine, but the wine is a great place to start. This is home to Brunello di Montalcino, one of Italy’s top reds, and fall is harvest time. Visit a winery, walk through the vineyards, or drive the hills while the leaves are changing. You’ll find local festivals around the grape harvest, and plenty of quiet trails with sweeping views along the way.
San Miniato: Truffles Everywhere
San Miniato is small but serious about truffles. Every November, the town becomes a hub for white truffle season, with markets, food stalls, and restaurants offering truffle menus for every budget. You’ll smell them before you see them. If you want to go deeper, you can book a truffle hunting tour with a local and their dog, then eat what you find.
Lucca: Chestnuts and Music
Fall in Lucca means roasted chestnuts, cakes, and even chestnut beer during the annual Festa della Castagna. The walled city transforms with food stalls and live music, and it’s one of the best places for a calm, scenic day outdoors. Walk the city walls, grab a bag of warm chestnuts, and stick around for the street performances that pop up during the festival weekends.
Pienza: Pecorino and Peaceful Views
If you’re after quiet towns with big views, head to Pienza. This little hill town is known for its pecorino cheese, which you’ll find infused with everything from truffle to herbs. The town itself is slow-paced, with cobbled lanes and sweeping fall views over the Val d’Orcia. Grab a bench, a wedge of cheese, and soak it all in.
Why Fall Is the Best Time to Visit Tuscany
Fall in Tuscany is about timing. The temperatures are cooler but still comfortable, the tourists are mostly gone, and the seasonal food is at its peak. You can spend the morning at a vineyard, the afternoon at a festival, and the evening in a quiet town eating something rich and local. Every town has its own way of doing fall, but everywhere you go, the rhythm of the season takes over.
If you want to understand why people fall in love with Tuscany, come in October. Skip the packed summer crowds, bring a jacket, and give yourself time to wander. You’ll see more and eat better—and you won’t forget it.
Know Before You Go
When to visit: Late September through mid-November, with peak foliage and festivals in October
How to get there: Florence is the main hub, but regional trains connect easily to Chianti, Lucca, and Siena
Where to stay: Agriturismos in the countryside, or base in Florence for day trips
What to pack: Layers, walking shoes, and something warm for chilly evenings
Planning More Fall Travel In Europe?
If you’re looking for other fall destinations, check out:
Fall in Champagne – Wine tastings, harvest season and quiet countryside towns
Fall in Zermatt – Cooler air, empty trails and Matterhorn views
Fall in Ljubljana – Cobblestone walks, riverside cafes and castle views
Fall in Budapest – Thermal baths, riverside walks and ruin pub nights
Fall in Copenhagen – Cozy weather, cinnamon buns and rollercoasters
Fall in Bavaria – Castles, forests and great beer
Fall in Amsterdam – Canals, stroopwafel and fall bike rides