For those who love to eat well, an off-season stay in a villa in Tuscany is an especially great idea during September as you can not only avail of the spoils of the harvest season, but you can also enjoy summer-like conditions and smaller tourist crowds – the best of both worlds! Not only will a trip at this time of the year mean that hearty autumn dishes will be served all over and all sorts of delicious things will be freshly harvested but it is also when many food festivals are held all across Italy and especially all across Tuscany. So, if you have found a villa with pool in Tuscany and you’re making the most of the almost-summer that is September, here are the food festivals that you should also check out!
The first Sunday of September
The ideal Renaissance town of Pienza is not only famous as an impossibly picturesque gem but it is also home to a local pecorino cheese known as cacio. On the first weekend of September each year, they celebrate this culinary heritage with a cheese festival. In addition to things to sample, shop, and savour during this celebration of their local cheese, there is also a special event that takes place in which playing with your food is very much encouraged. Called the Palio del Cacio Fuso, the aim of the game is to roll a wheel of cheese as close as possible to the designated target, the fuso, or wooden spindle, that is wedged between two bricks in the town’s main square.
Settembre DiVino, Pitigliano
The first weekend of September
This wine festival is named for a play on words and could be interpreted as either “divine September” or the “September of Wine.” No matter what way you read it, however, those who find a vacation rental in Grosseto should head to the town of Pitigliano during a September visit to the area if they love wine and the good life. Taking place over four days, it sees the local wine cellars carved out of stone in town open to visitors and all sorts of wine-related events take place. Ring in September with an excellent glass of local wine!
Chianti Wine Festival, Greve in Chianti
The second weekend of September
Of course, if you were going to book a holiday rental in Chianti for September, meanwhile, you would always expect your vacation to involve some incredible wine tastings but if you’re there over the second weekend of the month, you’ll really be able to do it right! As with Pitigliano’s event, this festival, based in Greve in Chianti, sees local wine cellars open to the public along with a packed itinerary of tastings, banquets, markets, talks, visits to wineries, and more. Tens of wineries from the surrounding area participate, allowing you to really dive into the famous wine of Chianti.
Fig Festival, Bacchereto
The first two weekends of September
Fig-lovers, meanwhile, should head to the small hamlet of Bacchereto in the municipality of Carmignano, located in the area around Prato, where there is an annual festival dedicated to the fruit. Held over the course of the first two weekends in September, it has a schedule of tastings and performances, various food and wine stands, and, of course, some incredible figs to indulge in!
Villaggio della Birra, Buonconvento
September 5th to September 7th 2025
Italy and Tuscany are better known for their wine but there are still some great opportunities for beer-lovers to indulge while on holiday in Tuscany, as well. From local craft brews to great beer bars, there are great ways to enjoy beer in Tuscany but, if you book a vacation rental in Siena over the course of the run of the Villaggio della Birra in Buonconvento then you’ll be able to find a gathering of both excellent local brews and international beers all in one spot! Started back in 2006 with just a few hundred people getting together to sample Belgian beers, now over 8,000 visitors come each year from all over Europe to sample the wares of micro-breweries in the area and an amazing curation of international brews.
There are many more food festivals to be discovered in little towns dotted all throughout Tuscany each September, this is merely an introduction to some of them. Plus, September is only the beginning of harvest season and autumnal foodie delights. Many more festivals take place in October and November. Lots of festivals that are not specifically dedicated to foods are also held throughout September in Tuscany but you’d best believe that food is still central to any of these events, no matter what! So, if you are considering a stay in one of our luxury villas in Tuscany in September and you want to dive into the local culinary scene, then you will find that you are in luck as there are all sorts of colourful, authentic, and exciting foodie experiences to be had!
