Why autumn is the best time for food and wine lovers to visit Chianti
Updated: 5 days ago
Discover the olive harvest, truffles, seasonal festivals and authentic flavours of Chianti from your base at Casalone.
There’s a saying in Italy that every season has its own flavour. Autumn is when many of the ingredients that make Tuscan cooking so comforting come together: new olive oil, porcini mushrooms, chestnuts, truffles, seasonal vegetables, hearty soups and stews. Depending on the restaurant and the timing of your visit, you may also find wild boar and other game on the menu.
Autumn in Chianti at a glance
Best time for: Food and wine holidays | |
Seasonal highlights: Wine harvest, olive harvest, truffles and chestnuts | |
Typical weather: Warm days, cool evenings | |
Don't miss: Fresh olive oil, porcini mushrooms and local food festivals |
Experience Tuscany's harvest season
The countryside around Casalone isn't simply beautiful – it's productive. October is when you'll see the Chianti landscape doing what it has done for centuries: producing exceptional food and wine. The days can still be warm, but without the crowds it feels less like a tourist destination and more like somewhere people are simply getting on with everyday life.
The vendemmia (grape harvest) usually runs through September into early October, with wineries processing the year's crop and preparing the next vintage. It's a fascinating time to visit family-run estates, although it's worth booking tastings in advance as producers are at their busiest.
With the grape harvest is drawing to a close, olive picking begins, woodland mushrooms appear on restaurant menus, and the first truffles of the season are celebrated in villages throughout the region.
The olive harvest and Casalone's own olive oil
From October onwards, olive groves across Chianti begin to fill with activity. Nets are spread beneath the trees, families gather to pick the fruit by hand and the olives are taken to the local mill within hours to preserve their freshness. Some olive farms offer opportunities to see the harvesting and pressing process.
Once the olives have been pressed, the freshly made oil has a wonderfully fresh, peppery character. If you see a local producer offering a tasting of the new oil, take the opportunity. Try it simply with good Tuscan bread and you will understand why olive oil is treated as an ingredient in its own right here.
At Casalone, we're fortunate to have our own olive groves. Every autumn our olives are harvested and pressed into extra virgin olive oil, and every guest receives a complimentary bottle to enjoy during their stay. It's one of the simple pleasures of being here. Don’t save it for a special occasion. Enjoy it throughout your stay as the Tuscans do – drizzled over tomatoes, grilled vegetables, soup or warm bread.
If you buy olive oil during your stay, look for oil from the current harvest, check the date of production, and choose either Tuscan Extra Virgin Olive Oil or EVO from Tuscany. It’s a very different experience from taking home a generic bottle labelled simply "Tuscan olive oil".
Truffles, porcini and the flavours of October
If summer belongs to tomatoes and basil, autumn in Chianti belongs to richer, earthier flavours.
Restaurants throughout the region begin serving seasonal dishes featuring:
Fresh porcini mushrooms
White and black truffles
Roasted chestnuts
Wild boar (cinghiale)
Pumpkin, beans and hearty Tuscan soups
The beauty of eating seasonally in Tuscany is that menus naturally change with the landscape. Rather than searching for tourist restaurants, look for smaller village trattorias where the daily specials reflect what's been harvested that week.
A foodie day trip: San Miniato
For serious food lovers, the medieval town of San Miniato is well worth visiting. Famous for its prized white truffles, it hosts one of Tuscany's best-known truffle celebrations (usually in November), alongside excellent delicatessens and artisan food shops.
Autumn food and wine festivals worth visiting
One of the pleasures of being in Tuscany in autumn is that food festivals tend to be local affairs – often centred around a village or small town rather than a large commercial event.
Here are a few to look out for:
Dit'unto – Villa a Sesta
This is one I would particularly recommend if you enjoy food and want something that feels genuinely local. Dit'unto is a festival dedicated, quite literally, to eating with your hands. It celebrates simple, wholesome country food and takes place in the small village of Villa a Sesta, near Castelnuovo Berardenga.
In 2026 it is scheduled for 11 October, from 11am to 8pm. The event brings together dozens of food producers and cooks, with food, wine, music and street entertainment.
It’s the sort of event that makes an autumn stay memorable: informal, sociable and centred around food.
L'Eroica, Gaiole in Chianti – food and village atmosphere
Even if you're not interested in cycling, the famous L'Eroica weekend brings wonderful food stalls, local wine and a lively atmosphere to Gaiole in Chianti in early October.
Boccaccesca, Certaldo
The much-loved festival of Boccaccesca celebrates Tuscan food, wine and regional producers in the beautiful hill town of Certaldo. Expect tastings, cooking demonstrations and plenty of opportunities to discover local specialities. The 2026 event is scheduled for 8–11 October.
Certaldo itself is worth visiting even without the festival, particularly the atmospheric upper town reached by funicular.
Village chestnut and mushroom festivals
Throughout October, dozens of smaller villages host sagre – traditional food festivals dedicated to chestnuts, mushrooms, truffles or olive oil. They're often inexpensive, wonderfully authentic and one of the best ways to experience local Tuscan life. The official Tuscany tourism calendar lists these events, where you can taste produce you might never encounter on a standard restaurant menu.
Why October is the perfect season for long lunches
By October, the intense summer heat has faded. Days are usually mild enough for outdoor lunches and countryside walks, while evenings are cool enough to justify a bottle of Chianti beside the fire.
Popular towns like Siena and Greve are still lively, but they're noticeably less crowded than in peak summer. That means easier restaurant reservations, quieter village streets and a much more relaxed experience exploring the region.
A few things that are different in October
There are a few practical things worth knowing before you arrive.
Some seasonal businesses will have changed their opening hours. Restaurants, wineries and attractions that operate mainly for the summer market may reduce their hours or close for part of the week.
Book restaurants you particularly want to visit. You don't need to plan every meal, but some smaller restaurants have limited opening days outside the high season.
Check winery availability. The harvest is a busy time for wine producers, so some wineries have limited availability for tours and tastings.
Don't assume every day will be warm. The weather can be glorious, but bring something warmer for evenings.
Use the quieter days to explore. Save the most popular destinations for weekdays where possible and use weekends for smaller villages, countryside walks and local events.
Stay at Casalone and taste the season
Autumn isn't about ticking off famous landmarks. It's about slowing down and enjoying Tuscany through its food.
Wake up at Casalone and see the changing season in the countryside around you. Head out for the day and you might come across an olive harvest taking place in a nearby grove. You may find a village celebrating chestnuts or local food. You could discover a tiny restaurant serving a mushroom dish that wasn't on the menu when you visited in summer.
And if the weather turns cooler? That's when Tuscany's autumn food starts to make perfect sense.
This time of year doesn't offer the certainty of a hot summer holiday. What it offers instead is something I think is much more interesting: seasonal produce and the chance to see Chianti as the locals experience it.
If you've visited Tuscany in summer, come back in the autumn. I think you'll discover a very different place – and quite possibly fall in love with it all over again.
Gallery - dawn mist at Casalone, early October
Dawn view from Casalone Casalone terrace at dawn Views from Casalone at dawn Early morning at Casalone
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