August 2026 in Tuscany & Umbria brings the year’s most concentrated stretch of tradition – the Palio dell’Assunta in Siena, a joust in Sarteano dedicated to San Francesco, barrel racing in Montepulciano, medieval weeks in Volterra and Città della Pieve, and an unbroken calendar of local sagre from valley to hilltop. Ferragosto falls on a Saturday this year, which means the festivities run long into the weekend.

Region-wide Highlights – August 2026 in Tuscany & Umbria

Cortona on the Move – All August

Now in its fourteenth edition, Cortona On The Move runs from July 16 through November 1, 2026, transforming Cortona’s palazzi, cloisters, and streets into open-air galleries. The 2026 artistic direction is entrusted to Renata Ferri, former chief photo editor of iO Donna, who brings a distinctly editorial sensibility to the selection. Exhibitions span documentary work, portraiture, and experimental visual storytelling. Free to walk; some venues by ticket.

Feast of San Lorenzo in Valiano – August 7 to 10

The hamlet of Valiano, a Montepulciano outlier perched above the Chiana plain, dedicates four days to its patron saint with a tractor rally and blessing, wine tastings, live music, and children’s shows. The highlight for those willing to stay late is the night of San Lorenzo itself — August 10 — when shooting stars are visible from the Rocca di Valiano with almost no light pollution. Bring a blanket and a good Nobile.

Volterra AD 1398 – August 9 and 16

On the second and third Sunday of August, Volterra becomes the year 1398. Volterra AD 1398 is one of the most immersive medieval re-enactments in Italy: knights, merchants, craftsmen, monks, flag-bearers, and jesters move through the Etruscan city from sunrise to sunset, recreating daily life in what was then a free commune. Markets, workshops, archery contests, and the minting of the grosso volterrano coin all take place in real historic spaces. This year’s editions fall on August 9 and 16 — the second date coinciding with Ferragosto week, so expect larger crowds on the 16th.

Palio dei Terzieri – Città della Pieve, August 10 to 23

For two weeks every August, Città della Pieve reverts to the era of its most famous son, Pietro Vannucci — il Perugino. The city’s three districts (Castello, Borgo Dentro, and Casalino) compete in archery, flag-throwing, and medieval games while their taverns serve centuries-old recipes. The final act on August 23 is the Caccia del Toro, a solemn archery competition preceded by a historical procession of over 800 participants in full Renaissance dress. One of the most authentically local events in Umbria — still largely undiscovered by mass tourism.

Sagra della Bistecca – Cortona, August 11 to 15

The 65th edition of Cortona’s Sagra della Bistecca takes over the Parterre gardens — a panoramic terrace above the Valdichiana — for five evenings running right through Ferragosto. The centrepiece is the world’s largest functioning grill, 14 metres in circumference and a Guinness Record holder, where Chianina T-bones weighing between 700 grams and 1.2 kilograms are cooked over wood. The menu is deliberately simple: steak, white beans or tomatoes, cantucci, Chianti. Come hungry, come early, and don’t expect a quiet table — this is a communal event in the best possible sense.

Sagra degli Strozzapreti – Paciano, August 10 to 17

Paciano — the walled Umbrian village that still feels genuinely unhurried — holds its summer sagra dedicated to the hand-rolled pasta strozzapreti for a full week. On August 9, the annual parade brings local children dressed in historic costume through the medieval streets; little Stella and her friends will be among them again this year. The sagra itself runs August 10 to 17 with outdoor dining, live music, and the kind of crowd that is almost entirely local. Details at the Pro Loco Paciano page.

Giostra del Saracino – Sarteano, August 14 and 15

The Giostra del Saracino di Sarteano is one of the oldest jousting traditions in Tuscany, and the 2026 edition carries extra weight: the palio banner is dedicated to San Francesco d’Assisi. Four contrade — San Lorenzo, San Martino, San Bartolomeo, and Santa Croce — compete for the painted banner in Piazza Bargagli, the village’s stone amphitheatre of a square.

The schedule for the August round runs as follows:

• Friday, July 31 to Sunday, August 2 — Contrada di San Lorenzo patron saint festival
• Tuesday, August 11 — Tratta dei Bossoli (draw of lots), Piazza Bargagli, 9:00 PM
• Friday, August 14 — Provaccia (practice joust), 4:00 PM
• Saturday, August 15 — Historical procession, 2:30 PM; Giostra del Saracino, 5:30 PM, Piazza Bargagli

Ferragosto evening in Sarteano, with a live joust in a medieval square and the smell of wood smoke in the air, is hard to beat.

Ferragosto – August 15

Italy’s most total holiday. The Assumption of Mary on August 15 means fireworks, long family lunches, shuttered shops, and nearly empty roads — until traffic returns with a vengeance on the 16th. This year Ferragosto falls on a Saturday, so the holiday atmosphere extends through the weekend. Plan your driving accordingly, book restaurants well in advance, and lean into it: the half-deserted hilltowns in the midday heat of August 15 have a stillness unlike any other day of the year.

Palio di Siena – August 16

The second Palio of the year — the Palio dell’Assunta — runs on Sunday, August 16, 2026. Ten of Siena’s seventeen contrade compete in the barebacks horse race around Piazza del Campo, which lasts roughly 90 seconds and is preceded by hours of ceremony, pageantry, and centuries of rivalry. The historical procession enters the Campo in the late afternoon; the race runs at around 7:00 PM. Standing room in the Campo is free; bleacher and window seats require advance booking well in advance — often months. Official information at ilpalio.org.

Calici di Stelle – August 10, Celle sul Rigo

On the night of San Lorenzo, the village of Celle sul Rigo opens its underground cellars for wine tasting under the stars — one of the more quietly beautiful traditions of the Val d’Orcia. Calici di Stelle takes place across dozens of Tuscan and Umbrian wine towns on the same evening, but the Celle sul Rigo edition, held in the village’s ancient cellars, has a particular intimacy to it.

Celle a Cena – Celle sul Rigo, August 9

The evening before Calici di Stelle, Celle sul Rigo hosts its community dinner centred on hand-made pici pasta — the thick, irregular spaghetti of the Val d’Orcia. Tables are set in the cellars and lanes of the village; the wine flows from the same producers who will be pouring the following night. A small, genuine event worth seeking out. Details via the Pro Loco Celle sul Rigo.

Sagra del Raviolo – Contignano, Val d’Orcia, August 13 to 16

The hamlet of Contignano near Radicofani dedicates Ferragosto weekend to hand-made ravioli — the egg-pasta parcels stuffed with ricotta and spinach or meat that every family in this corner of the Val d’Orcia makes from memory. The sagra is small, outdoor, and entirely unpretentious. Details at prolococontignano.it.

Fish Festival – Porto, Castiglione del Lago, August 10 to 15

On the shores of Lake Trasimeno, the lakeside hamlet of Porto hosts its annual sagra del pesce — fried and grilled freshwater fish, lake crayfish, bruschette, and cold local wine in plastic cups by the water. Informal, good-humoured, and genuinely local. Details at the Porto Sagra del Pesce Facebook page.

Sagra della Nana – Montallese

One of the genuinely odd delights of the Tuscan summer calendar: a tiny village near Montepulciano dedicates an evening to la nana — roast duck — with live music, local wine, and the most unexpected competition of the summer: guinea pig races for whole prosciutti. It is exactly what it sounds like, and it is entirely worth going. Only in Montallese, only in Tuscany.

Festa Contadina – Fabro, August 18 to 24

Fabro’s Sagra Contadina is one of the great farmer festivals of southern Umbria — a full week of grilled meats, field vegetables, handmade pasta, and folk music in a village that still operates on agricultural rhythms. Go early in the evening for a table; the queues form quickly and the portions are generous.

Festa della Cinta Senese – San Casciano dei Bagni, August 22 to 24

A three-day celebration of the Cinta Senese — Tuscany’s indigenous black-banded pig, once nearly extinct and now one of the region’s most prized Slow Food presidia. Lunch and dinner service each day, with a full menu of roast pork, finocchiona, lardo, ribollita, and pecorino. This is one of the best occasions of the year to taste products that rarely leave the area. Follow @sancascianoliving for updates.

Bravìo delle Botti – Montepulciano, August 22 to 30

The 52nd edition of Montepulciano’s Bravìo delle Botti culminates on Sunday, August 30 — as tradition demands, on the last Sunday of the month. Two competitors from each of the city’s eight contrade push an 80-kilogram wine barrel uphill along the Corso to Piazza Grande, racing for the painted bravio banner. The race itself lasts minutes; the preceding week of contrada dinners, rehearsals, and rivalry is the real substance of the event. The banner presentation takes place on August 23; the full programme at braviodellebotti.com.

Cortonantiquaria – August 28 to September 7

Now in its 63rd edition, Italy’s oldest antiques fair returns to the Sant’Agostino convention centre in Cortona’s historic core. Cortonantiquaria draws dealers, collectors, and exhibitions from across the country — furniture, paintings, silver, and objects spanning the 15th to early 20th century. Worth an afternoon even for non-collectors: the rooms are beautiful and the browsing unhurried.

Todi Festival – August 29 to September 7

Todi’s performing arts festival runs across the last days of August and into September, with theatre, classical music, dance, and outdoor cinema in the piazze and courtyards of one of Umbria’s most intact medieval cities. Programme and tickets at todifestival.it.

Weekly and Recurring Events

PICNICCO at Madrevite – Every Weekend

Most Saturday and Sunday afternoons throughout August, Madrevite — a Slow Food-selected winery near Panicale — hosts PICNICCO: wine tastings at sunset, local street food, and live music in the vineyard. It is the kind of event that requires no particular occasion to justify attending. Book in advance: +39 346.7953903 or +39 075.9527220.

Montalcino Weekly Market – Every Friday

Every Friday from 8:30 to 13:00, Via della Libertà in Montalcino fills with producers selling fresh vegetables, aged pecorino, breads, honeys, and the occasional bottle of young Rosso. A good reason to plan a Friday morning in town before the afternoon heat sets in.

Tips for August 2026 in Tuscany & Umbria

• Book ahead. Ferragosto weekend — especially August 15 and 16 — is the most congested stretch of the Italian summer. Restaurants, agriturismi, and event seats fill early.
• Go in the evening. Most sagre and festivals open at 7:00 PM or later. In August heat, this is not just a social convention — it is the only bearable time to eat outdoors.
• Avoid driving on August 15. Italian roads on Ferragosto are heavy with holiday traffic heading to the coast and back. Plan for a slow day, or stay put and enjoy the quiet of a nearly empty hilltown.
• Carry cash. Most local sagre and market stalls do not accept cards. An ATM visit before the evening saves frustration.
• Blend experiences. The region rewards the unhurried. An antiques fair in the morning, a swim at Lake Trasimeno at noon, and a contrada dinner in the evening — that is a good August day.

Need help planning a stay in Tuscany or Umbria in August? Country Slow Living offers holiday homes in the area — or write to Alina directly at countryslowliving@gmail.com or WhatsApp +39 338 740884.