On Friday night Arezzo dances to the nineties, on Saturday Cortona closes its jazz festival and Sansepolcro brings Italy’s great wineries to town for B.E.V.I., and on Sunday the city runs the Maratonina. Out in the villages there are the last chestnuts of Caprese Michelangelo, the Pumpkin Festival in Foiano and the flea market in Castiglion Fiorentino. Here are the nine events we picked, with times and addresses kept up to date.
1 Joya: Wannabe 90's vol. 1
Friday 23 October, at 21:30 · Il Principe, Arezzo
A whole night of nineties hits, from the Spice Girls and the Backstreet Boys to the Italian dance of Gigi D’Agostino and Eiffel 65. Dinner show from 21:30, then dancing from midnight with DJs Riccardo Ricci and Paolo Fei. Tables can be booked on 347 668 6969.
2 Cortona Jazz: Synthesis Collective con Fay Victor e Abraham Burton Quartet
Saturday 24 October, at 21:00 · Chiesa di San Domenico, Cortona
The festival’s closing night. At 21:00 the Synthesis Collective with singer Fay Victor plays in the Church of San Domenico, followed at 22:00 by the Abraham Burton Quartet: one ticket covers both concerts. Night owls can stay on for the jam session in Sala Pavolini from 23:30.
3 B.E.V.I. 2026: Borgo Eccellenze Vinicole Italiane
24–25 October · Centro storico di Sansepolcro (sabato) e Borgo Palace Hotel (domenica)
Two days devoted to Italy’s great wineries. On Saturday the programme in the old town is open to everyone, with tastings of local wines, live painting, jazz and an after party in the town hall cloister; on Sunday the producers pour their wines at the tasting tables of the Borgo Palace Hotel. Tickets are on TicketOne.
4 Visita guidata gratuita alla Casa Museo Ivan Bruschi
Saturday 24 October, at 11:00 · Casa Museo Ivan Bruschi, Arezzo
On Saturday the house museum of the antiques dealer Ivan Bruschi is free all day. At 11:00 there is also a free guided tour of the exhibition “Figure del ’900”, with works by Balla, Severini, de Chirico and Oppi.
5 Piper Opening: Dinner Show e Vanity Club Room 90/2000
Saturday 24 October, at 20:30 · River Piper, Castel San Niccolò
The Piper reopens with the first of its five nights of the season. Dinner show from 20:30, then from 23:00 two rooms: the nineties in the Piper Room and the 2000s in the Vanity Room. After dinner, entry is 15 euros with a drink included.
6 Festa della Zucca: Sapori d'Autunno
Saturday 24 October, at 16:00 · Centro storico di Foiano della Chiana
The old town of Foiano della Chiana fills up with pumpkins: street food, a farmers’ market, workshops for children, roaming music and shows. Saturday from 16:00, Sunday from 9:00. Entry is free and it is great for the whole family.
7 Festa della Castagna e del Marrone DOP
17–25 October · Caprese Michelangelo (centro)
Last weekend for the autumn festival in Michelangelo’s birthplace: PDO chestnuts and seasonal Tuscan cooking in the village centre until Sunday evening. A good excuse for a day out in the Valtiberina.
8 Maratonina Città di Arezzo, 27ª edizione
Sunday 25 October, at 09:00 · Piazza Guido Monaco, Arezzo
On Sunday morning Arezzo runs the 27th Maratonina: at 9:00 the half marathon and the 10.6 km race start from Piazza Guido Monaco, at 9:05 the 3.5 km fun run, open to everyone. Online entries for the competitive races closed on 22 October; everyone else can cheer along the course.
9 Amarcord, mostra scambio di cose vecchie e usate
Sunday 25 October, at 09:00 · Giardini Pubblici di Castiglion Fiorentino
On the fourth Sunday of every month the public gardens of Castiglion Fiorentino host this swap meet of old and second-hand things: antiques, vintage and collectables, from 9:00 to 19:00. Entry is free.