Tuscany witnesses nearly 50 million visitors annually and Fall is one of the most popular times to visit, especially for wine lovers.

September and October marks “vendemmia” meaning the wine grape harvest period. The region’s Queen grape is Sangiovese, defined by rustic notes of cherry, violet aromas and quaffable body. Expressions of Sangiovese vary based on the region it’s being crushed and bottled in. I.e. the verdant valleys of Montepulciano vs the rolling hills of Chianti Classico.

While reasonable to assume these months as the perfect time for wine cellar tours, it’s also one of the busiest as winemakers are under the wire to harvest and press, making it hard to welcome guests at their estates. 

Instead of wine cellar touring around Tuscany’s various villages, keep “feste di vino”, (i.e. wine festivals) held in the piazze (town squares) on your radar to soak up the region’s wine culture, traditional arts, and seasonal gastronomic specialties such as meaty bowls of pici pasta or slabs of wine grape flatbread schiacciata con l’uva (wine grape pie) to munch on. 

These cultural wine events with its many wine stands and pop-up enoteca cellars are also an optimal way to get to know a plethora of winemakers in one afternoon or evening. 

Here is a curated list of 5 festivals dedicated to wine around Tuscany, hand-selected by a sommelier living in Florence.

Festa dell’Uva Impruneta 

Less than a 30 minute drive or bus from Florence’s main center is the town of terracotta, Impruneta translated as “The land of pines.” Impruneta has hosted this wine fest since 1932 where 4 of the town’s key neighborhood Rione compete in rallies (gare). The fair was originally conceived to promote the consumption of grapes/wine in trying economic times. Costumed processions, ceramic handicraft stands, local Chianti wine and competing Rione banquets dominate the wine-filled weekend.  

Festa dell’Uva Chiusi

South of Montepulciano bordering Umbria at the edge of the Valdichiana Valley lies Chiusi. This is one of Tuscany’s ancient historic gems heralded for its impressive Etruscan ruins. Their annual wine festival involves tastings from around the whole of Italy with an emphasis on Umbria and Tuscany, fresh pici pasta and local nonne rolling out these thick strands in the square, street theater performances, DJ sets, folklore and local bands. 

In between wine tasting and noodle twirling, hit up some of the fascinating cultural attractions from catacombs, archaeological museum, Roman-era Labirinto di Porsenna labyrinth tower giving major Labyrinth movie nostalgia and underground ruins. 

Festa dell’Uva Maremma 

This under-the-radar gem of Southern Tuscany blooms into its most anticipated annual wine events boasting the area’s inky red Morellino di Scansano. Another underappreciated Tuscan hit, this wine is easy drinking elegance with notes of amarena cherries comprised primarily (85%) of a local clone of Sangiovese. It was put on the map by wine-maker Elisabetta Geppetti “la signora del Morellino” and this festa is a great way to meet more small producers proudly pressing it, along with live music, hand-cut prosciutto panini, sommelier-led tastings and more. 

Festa del Vino Montecarlo 

This small DOC wine region is located in convenient proximity to Lucca, which is good news for Tuscan vacationers who are taking a detour from hotspots like Florence and Siena. The wine here are based on the usual native suspects like Sangiovese, Ciliegiolo, Canaiolo and Trebbiano but with some international stars mixed in like Cabernet Sauvignon, Merlot and Syrah making these kitchen sink blends full of character. What better way to get to know this lesser-known DOC than with its annual week-long wine festival held in September including  traditional folk music, dance, street food stands in tandem with unique pop-ups like wine tasting under the stars. 

Chianti Wine Festival in Greve

Love the rustic, cherry punctuated red wines from Chianti Classico? This is the weekend-long wine event held every year in September since 1972 bringing nearly all of the consortium’s producers together in Greve’s main square to speed taste (or slowly explore your favorites). Very wine heavy with a few gastronomic stands for snacking, and some open art exhibits along with local band sets. Ideal for both aficionados and wine professionals. 

Bonus Wine Event tip for Chianti Classico lovers:

Vino al Vino in Panzano 

Held every third weekend in September, over 20 wine producers of the Panzano sub-region of Chianti Classico gather to show off their juice in the scenic hamlet’s main square Piazza Bucciarelli. You pay a day fee (starting from 30eu) for a glass to taste and sample around the stands. 90% of wine produced in Panzano is organic and defined by mostly small family-owned wineries. Win-win, or wine-win.