While summer is the most popular time to visit Italy, autumn is one of the best times to visit Tuscany and Umbria. The summer crowds have thinned out, the heat dials down and life slips into a gentle, alluring rhythm. And with harvest season in full swing, Italy’s delectable olive oils take centre stage as farms and groves come alive with activity.
Dubbed “the great healer” by Hippocrates and “liquid gold” by Homer, olive oil has a longstanding history across the country. Italy’s love affair with olive oil dates back to the Etruscans, since at least 800 BCE. By the time of the Roman Empire, olive oil production had evolved into a refined art and a cornerstone of daily life – in the kitchen and beyond. Today, that rich tradition lives on, where family-run groves still honour time-old traditions.
Both Tuscany and Umbria play host to a rich calendar of hyper-local harvest festivals and experiences. With our insider guide, you’ll be in on the best times and places to experience them. These celebratory events allow you to meet the producers, tour local mills and sample fresh olive oil straight from the press.
With over 35 years of expertise behind us, we work closely with villa owners to offer guests an immersive, insider experience. Some of our villas produce their own olive oil, with private tastings available from the comfort of your villa. Discover our collection of autumnal escapes.
Olive Oil Festivals in Tuscany
Festa dell’Olio – Sesto Fiorentino
Between September and November, olive oil mills across Tuscany hum with harvest. This warm and welcoming festival in Sesto Fiorentino is one of the most important olive oil festivals in Tuscany, held in a beautifully preserved medieval village. Travellers and locals come together to sip artisanal olive oil shoulder to shoulder over cheese boards and bruschetta. You’ll also get to learn all about the traditional methods of farming and oil production, which have been passed down through generations.
When: Early November
Where: Florence
Pro tip: Pick up fresh regional cheeses and local produce from the farmers’ market. Come evening, the piazza is filled with live music as locals join to dance the night away.
Festa dell’Olio – Valdambra
Located in the Valdambra valley, Bucine’s olive oil festival is in its fourth year of showcasing high-quality extra-virgin olive oil. The individual tastings showcase the best of the region, with the chance to meet with beaming local producers. It’s a day filled with delicious cuisine and olive oil tastings, with a trip to the Olivone olive mill included.
When: 1 December
Where: Bucine, Arezzo province
Pro tip: Wander around the lively village of Bucine and discover local community concerts and informative talks not to be missed.
Festa dell’Olio – San Quirico d’Orcia
San Quirico’s olive oil festival has been going since 1993, luring guests with its spectacularly scenic location. The olives have been grown in the area for centuries and will be on offer for travellers and locals to sample.
Highlights include intimate tasting sessions in Palazzo Chigi, a 17th-century palace steeped in grandeur and history. Stalls selling locally-crafted and artisan goods can be found outside Porta Nuova, and there’s also the chance to hop on an e-bike through the Val d’Orcia countryside followed by live music in town.
When: 5 – 8 December
Where: San Quirico d’Orcia
Pro Tip: Don’t miss the village nativity scene unveiled during the festival – it’s a superb local tradition that adds a festive touch to the celebrations.
Wine and Olive Oil Walk – Castagneto Carducci
For something a little different, why not embark on a laidback 10km walking tour through local olive farms and vineyards. Now in its third year, this annual event includes intimate olive oil tastings and mini-classes while en route, stopping at estates in Bolgheri and Catagneto Carducci along the way. You’ll get to meet small producers and learn all about their sustainable methods.
When: October
Where: Castagneto Carducci
Pro tip: Wear comfortable shoes and pace yourself – the walk winds through vineyards and olive groves, and the tastings are plentiful!
Sagra dell’Olivo – Canino
Sagra dell’Olivo festival in Canino is Italy’s oldest olive oil festival, dating as far back as 1939. Highlights include the chance to taste bruschetta served with freshly pressed olive oil in Canino’s main piazza.
Visitors are welcome to sample the renowned Canino DOP extra virgin olive oil, known for its emerald green hue with balsamic tones. Guided visits to atmospheric olive mills are also on the agenda this time of year.
When: Early December
Where: Historic centre of Canino in Lazio
Pro tip: Stay at the beautiful Elaios near Viterbo for its close proximity to the surrounding olive groves.
Olive Oil Festivals in Umbria
Frantoi Aperti – Umbria
Known as the “green heart of Italy,” Umbria’s landscape is dominated by olive groves. Every October and November, Frantoi Aperti festival lures thousands of olive oil enthusiasts to Umbria, offering a month-long roster of tastings and immersive experiences unique to the region.
Umbria is home to five distinct EVO zones, each with its own flavour and character. As one of Italy’s largest olive oil events, the festival is spread across the region’s stunning towns, including Montefalco, Orvieto, Trevi, Spello and Todi.
Not only is there plenty of delicious olive oil to taste, but also complimentary tours of mills and groves. The festival atmosphere is rounded out with informative exhibitions, live music and plenty of games and activities for children.
When: 18 October – 16 November
Where: Scattered all across Umbria’s hilltop towns – Orvieto, Trevi, Spello, Todi, Montefalco and Giano dell’Umbria.
Pro tip: Don’t try to do it all in one day – pick a couple of towns, take it slow and enjoy the tastings (and the views!) along the way.
La Mangiaunta – Giano dell’Umbria
Taking place in November, Giano dell’Umbria’s is a celebrated olive oil festival in the heart of Umbria. Along with immersive tastings and guided tours of the local mills, the festival is home to its own unique traditions. The Frasca Tour is a brilliant way to explore the olive groves on foot, stopping at various frasche – small, rustic eateries in remote locations – along the way.
When: 1 – 3 November
Where: Giano dell’Umbria
Pro tip: Arrive early to catch the olive oil pressing demonstrations at the local mills.
UNTO – Assisi
From 29 October to 27 November, Assisi in Umbria comes alive during the harvest with UNTO, a festival celebrating its prized extra virgin olive oils. Throughout the festival, visitors can delve into the region’s rich olive oil heritage and learn all about its distinct, regional characteristics. You’ll get to see firsthand the meticulous process of cold pressing, traditionally done by hand to preserve the oil’s purity.
When: 29 October – 27 November
Where: Assisi
Local Tip: Many producers offer mini-workshops, where you can learn to pair olive oil with Umbrian breads, cheeses and seasonal dishes.
Where to stay in Tuscany and Umbria
Make one of our handpicked villas your base for olive oil tasting in Italy. Each villa in our autumn portfolio is carefully selected for its character, comfort and proximity to the region’s best olive groves.
Enjoy the ease of our complimentary concierge, who can arrange bespoke experiences, including private olive oil tastings, a tour of the best olive oil mills across Tuscany and Umbria, as well as local intel on the festivals taking place.