A local guide to visiting Tuscany and Umbria in September 2026, including festivals, harvest season, food and wine experiences, villages and things to do.

For  travelers, September offers something particularly special: the opportunity to experience Tuscany and Umbria beyond Florence, Siena and Rome.

2026 planning note: Event schedules can change, particularly for small village festivals. Dates marked TBC have not yet been officially confirmed for 2026 and should not be treated as final.

September 2026 Events in Tuscany and Umbria.

• September  4–October 24: Pan Opera Festival — Panicale, Paciano & Città della Pieve.

  The Pan Opera Festival has become an important cultural event around Lake Trasimeno.
  In 2026, the festival runs from September 4 through October 24, with opera, concerts, sacred music and musical theater presented in historic churches, theaters and other venues in Panicale, Paciano and Città della Pieve. For  travelers who love classical music, this is an excellent reason to spend several nights around Lake Trasimeno rather than simply passing through.  2026 dates: September 4–October 24

Area: Panicale, Paciano and Città della Pieve

•  September 4–6: Villaggio della Birra — Rapolano Terme Wine may dominate Tuscany’s September calendar, but beer lovers have something to celebrate too.

  The Villaggio della Birra returns to Rapolano Terme from September 4–6, 2026.

The festival brings Italian and international craft breweries together with tastings, workshops, live music and food.It is a fun stop for travelers exploring the area between Siena, the Val di Chiana and the Crete Senesi.

2026 dates: September 4–6
Location: Rapolano Terme, Tuscany

• September 5–6:  Arezzo Antique Fair

  The historic Arezzo Antique Fair takes place on the first Sunday of every month and the preceding Saturday. Arezzo’s Piazza Grande fills with antiques, collectibles, vintage objects, furniture and curiosities, making it an excellent stop for travelers who want to bring home something more memorable than a souvenir T-shirt.

Fiera Antiquaria di Arezzo. 2026 dates: September 5–6 – Location: Piazza Grande, Arezzo

• September 6: Giostra del Saracino — Arezzo

  One of the biggest events of the September calendar is the Giostra del Saracino in Arezzo.
  The September 2026 edition is particularly special because it will be the 150th edition.

The joust takes place on Sunday, September 6, 2026, in Piazza Grande. The official program also includes the general rehearsal on September 4. Expect costumed processions, flag throwers, musicians, horses and the dramatic medieval-style competition between Arezzo’s historic quarters. For first-time visitors to Tuscany, this is one of the events we would put at the top of the list.

Main event: September 6, 2026
General rehearsal: September 4
Location: Piazza Grande, Arezzo

• August 31 to September 6: Festa del Cacio — Pienza

  If you love Italian food, don’t miss Pienza’s Festa del Cacio.

  The 64th edition takes place from August 31 through September 6, 2026, with the main cheese fair on September 5 and 6.

The festival celebrates Pecorino di Pienza, one of Tuscany’s most famous cheeses. There are tastings, local products, traditional games and the famous Gioco del Cacio al Fuso. For American food travelers, this is an easy event to combine with a day exploring the UNESCO-listed Val d’Orcia.

september in tuscany

2026 dates: August 31–September 6
Location: Pienza, Val d’Orcia

• September 7: Festa della Rificolona — Florence. If your September trip includes Florence, save September 7 for the traditional Festa della Rificolona, or Festival of the Lanterns.

  The celebration fills the city with colorful paper lanterns and is one of Florence’s beloved end-of-summer traditions.

Date: September 7, 2026
Location: Florence

• September 3–5 and 10–12: Live Rock Festival — Acquaviva di Montepulciano

  The Live Rock Festival returns to Acquaviva, near Montepulciano, over two September weekends.

The festival combines international music with cultural programming and takes place at the Giardini Ex Fierale in Acquaviva. This is particularly convenient for travelers staying in Montepulciano, Pienza, Chiusi or the Val d’Orcia.

2026 dates: September 3–5 and September 10–12
Location: Acquaviva di Montepulciano

• September 10–13: Expo Chianti Classico — Greve in Chianti
  For American travelers who love wine, this should be high on your September itinerary.
  The 54th Expo Chianti Classico takes place in Greve in Chianti from September 10–13, 2026.

Winemakers from across the Chianti Classico territory gather in Piazza Matteotti, giving visitors the opportunity to taste wines directly in the heart of the region where they are produced. The 2026 edition includes 64 wineries.

2026 dates: September 10–13
Location: Greve in Chianti

A tip for American wine travelers. This is a much more immersive experience than simply buying a bottle of Chianti at a restaurant in Florence. You can meet producers, taste different styles of Chianti Classico and learn about the territory directly from the people who make the wine.

• September 11–15: Festa dell’Uva — Panicale

  The grape harvest is one of the defining themes of September in Umbria.

  The Festa dell’Uva e dei Prodotti Tipici in Panicale takes place from September 11–15, 2026.

For travelers staying near Lake Trasimeno, Panicale is an especially attractive September destination because the festival can be combined with a visit to one of Umbria’s most beautiful hill towns.

2026 dates: September 11–15
Location: Panicale, Umbria

• September 13: Palio dei Ciuchi —vcvcf Asciano

  The Palio dei Ciuchi, or Donkey Palio, is held in Asciano on the second Sunday of September.
  In 2026, that falls on Sunday, September 13.

This colorful village tradition features historic costumes, flag throwers, local food and the unusual donkey race.For American visitors looking for an experience away from the major tourist centers, Asciano offers exactly that.

Date: September 13, 2026
Location: Asciano, Crete Senesi

• September 13: Giostra della Quintana — Foligno

  Umbria’s great historical event in September is the Giostra della Quintana in Foligno.
  The 2026 edition of La Rivincita culminates on Sunday, September 13 at Campo de li Giochi. The historic procession takes place on Saturday, September 12, followed by the joust on Sunday afternoon. Foligno’s historic center becomes a stage for Renaissance costumes, neighborhood rivalries and one of Umbria’s most spectacular equestrian traditions.

Procession: September 12, 2026
Joust: September 13, 2026
Location: Foligno, Umbria

• September 18–20: Enologica Montefalco — Umbria

  Wine lovers should continue south into Umbria for Enologica Montefalco – Abbinamenti.
  The 2026 event takes place from September 18–20.

The festival brings together Montefalco Sagrantino DOCG, Montefalco DOC and Spoleto DOC wines with Umbrian food, art, music, workshops and winery. For American visitors interested in Italian wine, Montefalco is one of Umbria’s most rewarding alternatives to the better-known wine destinations of Tuscany.

2026 dates: September 18–20
Location: Montefalco, Umbria

• September 18–20: Vino al Vino — Panzano in Chianti TBC

  Just after Expo Chianti Classico, wine lovers can continue to Panzano in Chianti for Vino al Vino.
  The event traditionally takes place during the third weekend of September, with the preceding Thursday and Friday.
  Expected 2026 dates: September 18–20

Location: Piazza Bucciarelli, Panzano in Chianti

• Corsa di Pio – Pienza | September 18–20, 2026

The Corsa di Pio is a historical reenactment held in Pienza, bringing the Renaissance atmosphere of the town back to life. From September 18 to 20, the streets fill with period costumes and celebrations recalling the foundation and history of this remarkable Tuscan town.

• September  20/21  25/26 and to  29 settembre 2026  Sagra dell’Ocio — Montepulciano Stazione. One of the more unusual food festivals on the original Tuscany Umbria Blog list returns in September. (Dinners opening at 7:30 pm).

2026 dates: September 20–29
Location: Montepulciano Stazione

• September 26–28: Festa dell’Uva e del Vino — Chiusi

  The Festa dell’Uva e del Vino in Chiusi is another September tradition that should be on the radar of wine-loving travelers.

The festival features local wines, traditional food, music and events throughout the historic town.

2026 main festival: September 26–28
Preview: September 20–25
Location: Chiusi, Tuscany

• September 24–27: I Primi d’Italia — Foligno

  The month ends with one of Umbria’s great celebrations of Italian food.

  I Primi d’Italia is dedicated to Italy’s primi piatti: pasta, rice, soups, gnocchi and other traditional first courses.

The festival traditionally takes place in late September in Foligno.

What About the Other Events From Our Original September Guide?
Some of the events listed in the original Tuscany Umbria Blog article are still important local traditions, but we do not recommend publishing an exact 2026 date until the organizers confirm it.
These include:

Moiano Local Pork Festival

The original article listed the local pork festival in Moiano for September 2. We have not found sufficiently reliable confirmation of a 2026 date, so this should remain TBC.

• Mille e Una Umbria — Paciano

The traditional Paciano food and culture event remains associated with the village, but a reliable 2026 date was not available in the sources checked.

• Montalcino Honey Week

Honey Week remains a traditional September event in Montalcino, but a definitive 2026 event date was not found in the official sources ch
Monte San Vito and Passignano Events

• The Best September Events for American Travelers
  If you only have time for a few events, these would be our top choices:
  🏇 For history: Giostra del Saracino
  Arezzo — September 6
  The 150th edition makes 2026 particularly special.
• 🧀 For food: Festa del Cacio. Pienza — September 5–6. A perfect combination of Pecorino, medieval streets and Val d’Orcia scenery. Pro Loco Pienza
• 🍷 For wine: Expo Chianti Classico
  Greve in Chianti — September 10–13. One of the best opportunities to taste Chianti Classico directly from producers. Expo Chianti Classico
• 🍇 For harvest traditions: Festa dell’Uva. Panicale — September 11–15. A beautiful introduction to Umbrian wine and rural traditions.
  🍷 For serious wine lovers: Enologica Montefalco. Montefalco — September 18–20
• 🏰 For medieval Italy: Giostra della Quintana. Foligno — September 12–13. One of Umbria’s most spectacular historical celebrations.

How to Plan a Tuscany and Umbria Trip From the USA
For American travelers, September is an excellent time for a 10–14 day Italy itinerary.
A practical route could look like:

Days 1–3: Florence
Explore Florence before heading into the countryside.

Days 4–6: Chianti & Siena
Attend Expo Chianti Classico and visit wineries.

Days 7–9: Val d’Orcia
Stay near Pienza or Montepulciano and experience the Festa del Cacio and local wine country.

Days 10–12: Lake Trasimeno & Umbria
Explore Panicale, Paciano and Montefalco.

Days 13–14: Foligno or Orvieto
Finish with Umbrian food, wine and historic towns before continuing to Rome.

And if you are staying at or near Il Fontanaro, many of these events are within easy reach for an half day trip.

For American travelers looking for an authentic Italian vacation. These events offer something that the major tourist attractions cannot: a chance to experience Tuscany and Umbria as the locals do.

Come for the Renaissance history. Stay for the wine. Eat the Pecorino. Walk the medieval streets. And, if you are lucky enough to visit during the vendemmia, raise a glass to September in Italy.

Benvenuti in Toscana e Umbria!

Date Event Location
Aug. 28–Sept. 6 Ruzzi della Conca Chiusi
Sept. 1–13 Palio della Balestra Sansepolcro
Sept. 3–5 & 10–12 Live Rock Festival Acquaviva
Sept. 4–Oct. 24 Pan Opera Festival Panicale / Paciano / Città della Pieve
Sept. 4–6 Villaggio della Birra Rapolano Terme
Sept. 5–6 Arezzo Antique Fair Arezzo
Sept. 5–6 Festa del Cacio Pienza
Sept. 6 Giostra del Saracino Arezzo
Sept. 7 Festa della Rificolona Florence
Sept. 10–13 Expo Chianti Classico Greve in Chianti
Sept. 11–15 Festa dell’Uva Panicale
Sept. 11–13 Pienza International Music Festival Pienza
Sept. 13 Palio dei Ciuchi Asciano
Sept. 12–13 Giostra della Quintana Foligno
Sept. 18–20 Enologica Montefalco Montefalco
Sept. 18–20* Vino al Vino Panzano in Chianti
Sept. 20–29 Sagra dell’Ocio Montepulciano Stazione
Sept. 24–27* I Primi d’Italia Foligno
Sept. 26–28 Festa dell’Uva e del Vino Chiusi