A region synonymous with world-class wine, Tuscany’s winegrowing tradition dates back to the ancient Etruscans more than 2,000 years ago. Throughout history, generations of winemakers have perfected their craft, producing world-famous wines such as Chianti Classico, Brunello di Montalcino and the modern Super Tuscans.
Tuscany is now home to a calendar of wine festivals throughout the year, organised all over the region to celebrate its rich wine heritage. From Chianti to Montalcino, countless local wineries – big and small – take part, welcoming visitors for tours and tastings. During the festivities, you’ll often get to meet the winemakers up close and learn about their techniques and traditions, which vary from vineyard to vineyard.
To elevate the experience, we have a selection of luxury villas in Tuscany set among vineyards and within easy reach of some of the region’s best-known wine towns. Allow our award-winning Concierge to create a personalised itinerary from the moment you arrive, including sommelier-led tastings from the comfort of your villa. Whether you’re heading to the hills of Chianti or Montalcino, these are the wine festivals in Tuscany to bookmark now.
Terre di Toscana, Lido di Camaiore
Tuscany’s unspoiled coastline is home to an underrated food and wine scene. Taking place in March, this superb wine tasting event brings producers from across Tuscany to Lido di Camaiore, a coastal town in Versilia. The two-day event showcases both new releases and established labels. Old vintages are also be available for tasting, a tradition that usually takes place on a Monday.
Make Villa Denise your base, a luxury villa within easy reach of Lido di Camaiore and the Versilia coast. Set along the coast, the estate produces its own organic red and white wines on site, with private in-villa wine tastings and dining included upon request.
Festa del Vino, Chianti
From late May into early June, the village of Montespertoli comes alive with Mostra del Chianti, a terrific local wine festival for diving into the region’s traditions, practices and rich viticulture. The village is best known for its producers of wine and olive oil, such as Castello Sonnino.
To make the most of the festival, secure your stay at Villa d’Elsa for its prime location on an 80-acre estate in the Chianti countryside. Days unfold with home-cooked Tuscan meals and trips to local wineries, who open their doors for immersive tastings and sommelier-led tours.
Jazz and Wine Festival, Montalcino
It’s not every day you get to sip Tuscan wine and enjoy live jazz amid one of Italy’s most esteemed wine towns. Montalcino’s week-long Jazz and Wine Festival brings Italian and international musicians to Castello Banfi and the Fortezza di Montalcino each summer, filling these historic settings with live jazz.
Looking for a base? Bel Sentiero makes a natural choice, set on the slopes of Monte Amiata with panoramic views across the Val d’Orcia. Montalcino is within easy reach, along with Pienza, San Quirico and other celebrated wine towns, making the villa an ideal base for exploring southern Tuscany between festival events.
Cantine Aperte, Various Locations
Scattered across Italy, Cantine Aperte (Open Cellars) is one of the country’s best-known celebrations of wine tourism. Over the last weekend in May, wineries in Tuscany open their doors for the occasion, welcoming locals and visitors to wander through the vineyards and sample delicious regional wines.
During Cantine Aperte in Vendemmia, which takes place in September and October, visitors can soak up the harvest season atmosphere with cellar openings and events celebrating the grape harvest.
In-villa wine tastings and tailored culinary experiences can be arranged at Il Cornello, a spectacular 17-person villa with easy access to southern Tuscany and the Val d’Orcia. In between winery visits, try truffle hunting in Monticchiello and sample seasonal Tuscan dinners prepared by local chef Bianca.
Expo Chianti Classico, Greve in Chianti
If you find yourself in Chianti in September, then you’re in for a treat. Greve’s annual Expo Chianti Classico sets the scene for a few days of wine-fuelled fun. Piazza Matteotti in Greve becomes a wine hub for tastings, bringing together producers from across the Chianti Classico denomination.
As the farmers prepare for the vendemmia (grape harvest), base yourself at Villa Alibizi for wood-fired pizza parties and wine experiences aplenty. The villa’s prime location in the Chianti countryside makes it an ideal base for making the most of the festival’s roster of cultural events, from guided tastings to cooking masterclasses.
Boccaccesca Festival, Certaldo
Those who appreciate wine, literature and Italian gastronomy should venture straight to the Boccaccesca Festival in Certaldo, a four-day festival traditionally held in October that pays homage to Giovanni Boccaccio.
The author of the Decameron was born in Certaldo, an ancient town in the heart of Val d'Elsa, which comes alive with local food, wine, cooking demonstrations and tastings throughout the festival. With a stay at La Piccinina or Disapero, discover Certaldo’s homegrown produce made by local artisans and sample regional wines in a convivial atmosphere.
Calici di Stelle, Montepulciano
Montepulciano is renowned for its Vino Nobile di Montepulciano and Rosso di Montepulciano, showcased every year at Calici di Stelle. Held every August, the festival features an immersive programme of events, from tastings at sunset, moon-lit walks through vineyards, rural picnics, live music and incredible stargazing opportunities.
Surrounded by vineyards, Dadianora is a 240-acre estate conveniently located for visiting Montepulciano’s excellent wineries. Enjoy Tuscan cuisine prepared by your private chef, pasta-making workshops, family-style pizza parties and bespoke wine tasting experiences from the comfort of your villa.
Bacco Artigiano, Rufina
At the end of September, Tuscany’s Rufina comes alive with Bacco Artigiano, a wine festival in the rolling hills northeast of Florence. The four-day celebration centres on wine and traditional produce from the Rufina area, with tastings, local food and a few Tuscan surprises along the way.
Just 7km from Rufina, The Estate of Petroio offers a world of its own, set on a 900-acre Chianti wine and olive-oil estate. Want for nothing at this fully staffed retreat, where you’ll be treated to sommelier-led in-villa wine tastings, truffle hunting in the Chianti hills and fun-filled alfresco barbecue evenings.
Contact our Villa Specialists
Whether you're a seasoned connoisseur or a curious beginner, our handpicked portfolio of food and wine villas offers an authentic way to experience Tuscany. Whether you’d like to arrange chef-prepared meals or private in-villa wine tastings, no request is too big or too small.
Our Private Cellar experience can also be arranged during your stay, with a dedicated sommelier selecting wines tailored to your tastes and the occasion. Connect with our Villa Specialists today for bespoke tips and tailored advice; they can match you with the perfect villa, arrange sommelier-led tastings and assist with any special requests.