Wine Festivals in Tuscany: Celebrate the Harvest, Wine & Culture
Updated: Oct 5
Celebrate the harvest, the wine, and the culture that defines Tuscany.
There is something special about visiting Tuscany at any time of year. But arrive when one of its wine festivals is taking place and the entire experience changes.
The quiet piazzas fill with tables and wine glasses. Winemakers leave their vineyards and cellars and come into town carrying bottles. Local restaurants move tables outside. Music echoes between medieval stone buildings. Children run through the streets while locals who seem to know everyone stop every few feet for another conversation.
And somewhere nearby, grapes are being harvested.
This is Tuscany when wine becomes more than something poured into your glass. It becomes part of the celebration happening around you.
Tuscany's wine festivals range from intimate gatherings where you may spend twenty minutes talking with the person who actually made the wine to enormous town celebrations with food, music, parades, medieval costumes and streets filled with people.
For travelers interested in Tuscany's wineries, we think these festivals add another dimension to a wine-country trip.
You can spend the morning visiting wineries and walking through vineyards, then spend the evening wandering through a medieval town with a tasting glass hanging around your neck.
That is a pretty good day in Tuscany.
“To experience Tuscany during harvest is to experience it at its most alive.”
Why Tuscany's Wine Festivals Are Worth Planning a Trip Around
Wine festivals give you something that even a great winery tour cannot completely reproduce.
They bring the entire wine community together.
Instead of driving from winery to winery, suddenly dozens of producers are standing within walking distance of one another.
You can taste a Chianti Classico from one hillside, walk twenty feet and taste another grown just a few kilometers away.
More importantly, you can talk to the people making them.
That is one of our favorite parts.
Tuscan wine becomes much more interesting once you begin connecting bottles with families, vineyards, villages and landscapes.
And the wine is only part of the experience.
Depending on the festival, expect some combination of:
Open-air wine tastings and conversations with winemakers
Traditional Tuscan food and street-food vendors
Live music, flag throwers and performances
Historic piazzas transformed into outdoor celebrations
Medieval costumes and neighborhood competitions
Special winery dinners and guided tastings
Local crafts and regional products
Vineyard and cellar events
Harvest celebrations
A surprising number of opportunities to eat something wonderful
Some festivals are really about serious wine tasting.
Others are about throwing the doors open and celebrating.
We recommend experiencing both.
The Best Wine Festivals in Tuscany
Radda nel Bicchiere — Radda in Chianti
When: Usually late May
Where: Radda in Chianti
Wine Region: Chianti Classico
If you want a festival where the wine itself remains the star, Radda nel Bicchiere is one of our favorites.
For one weekend, beautiful little Radda in Chianti essentially turns itself into an outdoor wine cellar.
The festival is organized by the local Pro Loco, and producers from around Radda set up throughout the village to pour their wines and talk directly with visitors.
The 2026 event took place May 23–24. More than 30 local producers participated, and the program included tastings, seminars, older vintages and the special Radda Vintage tasting.
What makes this festival particularly appealing is the setting.
Radda is already one of those places where you naturally slow down. Medieval stone buildings, narrow streets and sweeping Chianti countryside surround you.
Now imagine walking through it with a wine glass, moving from producer to producer.
That is Radda nel Bicchiere.
It is also an excellent opportunity to understand how much variation exists within Chianti Classico. Taste several Radda wines side by side and you begin noticing differences that are much harder to recognize when visiting wineries days apart.
Why we would go: Wine-focused, intimate and one of the easiest ways to meet numerous Radda producers in a single weekend.
Cantine Aperte — Open Cellars Throughout Tuscany
When: Usually the last weekend of May
Where: Participating wineries throughout Tuscany
This one is different.
Instead of bringing wineries into one town, Cantine Aperte brings travelers directly into the wineries.
Organized nationally by Movimento Turismo del Vino, Cantine Aperte—literally “Open Cellars”—encourages participating wineries to open their doors for special wine-tourism experiences.
In 2026, the main event took place May 30–31.
Depending on the winery, that can mean tastings, vineyard walks, food pairings, music, cellar tours or special events that aren't normally available.
For travelers using Tuscany as a road-trip destination, this is a particularly interesting weekend.
Instead of asking, Which winery should we visit?
The better question may be:
How many can we reasonably fit into one day?
Just remember that “reasonably” becomes a very flexible word in Tuscany.
Our advice: Pick a geographic area rather than trying to cross the region. Choose Chianti, San Gimignano, Montalcino or Montepulciano and build your day around participating wineries nearby.
And designate a driver.
Summer Wine Festivals in Tuscany
Calici di Stelle — Montepulciano
Around August 10
Calici di Stelle—“Glasses of Stars”—combines two things that are already pretty spectacular on their own: Vino Nobile and Montepulciano after dark.
During the celebration, wine producers pour their wines throughout Montepulciano's historic center as visitors wander its ancient streets carrying tasting glasses.
As the afternoon heat disappears, Piazza Grande and the surrounding streets fill with wine, food and music.
There are wine festivals, and then there is drinking Vino Nobile beneath the stars in a Renaissance hill town.
This is one we'd put on the calendar.
Bravìo delle Botti — Montepulciano
Late August
Imagine racing an enormous wine barrel uphill through the steep streets of Montepulciano.
That's the Bravìo delle Botti.
Montepulciano's eight historic contrade compete by pushing heavy wine barrels through town toward Piazza Grande.
If you've ever walked uphill through Montepulciano, you'll appreciate just how crazy that sounds.
The celebration extends far beyond the race, with historic processions, flag throwers, neighborhood dinners, costumes, wine and events throughout town.
This is less of a traditional wine tasting and more of an opportunity to experience the culture surrounding one of Tuscany's great wine towns.
September: Harvest Season in Tuscany
September is one of our favorite times to visit Tuscany.
This is vendemmia—the grape harvest.
Vineyards are filled with activity. Grapes arrive at wineries. Fermentation begins. Tractors appear on roads that seemed deserted only weeks earlier.
And almost every weekend seems to give another Tuscan town a reason to celebrate.
Expo Chianti Classico — Greve in Chianti
Usually the Second Week of September
Greve's famous Piazza Matteotti becomes an enormous outdoor tasting room during Expo Chianti Classico.
Producers from across the Chianti Classico territory gather to showcase their wines, making this one of the easiest places to explore the diversity of the region.
Taste a wine from Greve.
Then Radda.
Then Gaiole.
Then Castellina.
Suddenly you begin realizing that Chianti Classico isn't simply one wine.
The differences between villages, vineyards, elevations and winemaking styles become much easier to appreciate when you can taste them side by side.
Even better, you may discover a winery you love and decide to visit it the following day.
Vino al Vino — Panzano in Chianti
Usually the Third Weekend of September
Just down the road from Greve, Panzano offers a smaller and more intimate celebration.
During Vino al Vino, local winemakers gather in Piazza Bucciarelli to pour their Chianti Classico and Toscana wines.
What we particularly like about this festival is its focus.
You're not attempting to taste all of Tuscany.
You're tasting Panzano.
Take your time, talk with the winemakers and ask questions. The person pouring your glass may own the winery or have worked the surrounding vineyards for years.
Those conversations can become as memorable as the wines.
Festa dell'Uva — Impruneta
Last Sunday of September
Impruneta's Festa dell'Uva has been celebrating grapes and the harvest for a century.
The town's historic districts compete with elaborate floats, costumes, performances and displays that transform the center of town into an enormous celebration.
This isn't primarily about standing at a table analyzing wine.
It's about understanding what grapes, agriculture and the harvest mean to a Tuscan community.
For families especially, this can be one of the more entertaining harvest festivals because there's so much happening beyond wine tasting.
Festa dell'Uva e del Vino — Chiusi
Late September
The historic center of Chiusi fills with wine, local food, music, entertainment and neighborhood taverns during its annual grape and wine celebration.
This is the kind of Tuscan festival where our best advice is simply to wander.
Follow the music.
Try another cellar.
Sit down when something smells too good to pass.
Order whatever everyone else seems to be eating.
And don't worry too much about the schedule.
Sometimes realizing you've completely lost track of time is a pretty good indication that you're doing Tuscany correctly.
October in Tuscany
L'Eroica — Gaiole in Chianti
Usually the First Weekend of October
Technically, L'Eroica isn't a wine festival.
We think it belongs here anyway.
Created in Gaiole in Chianti, this famous vintage cycling event celebrates Tuscany's beautiful strade bianche, or white gravel roads.
Cyclists dressed in vintage-style clothing ride classic bicycles through vineyards, past castles and across the rolling hills of Chianti.
You don't need to ride to enjoy it.
Gaiole becomes a celebration filled with vintage bicycles, markets, food, music and, naturally, plenty of Chianti.
L'Eroica celebrates something essential about Tuscan wine that is easy to overlook:
The wine and the landscape are inseparable.
Cantine Aperte in Vendemmia — Harvest at the Wineries
September–October
Visiting a quiet Tuscan vineyard is wonderful.
Visiting during harvest is completely different.
During vendemmia, wineries suddenly come alive. Grapes arrive from the vineyards, equipment is running, workers move between the cellar and crush areas, and fermentation begins.
Participating wineries throughout Tuscany offer special harvest experiences during Cantine Aperte in Vendemmia.
If you're visiting during September or early October, look for wineries offering harvest activities.
You'll never look at that finished bottle quite the same way again.
November in Montalcino
Benvenuto Brunello — Montalcino
November
For serious wine lovers, Tuscany's festival season isn't over when the harvest ends.
Benvenuto Brunello brings wine professionals, producers and enthusiasts to Montalcino for the presentation of newly released Brunello vintages.
This isn't the parade-and-street-party atmosphere you'll find at some harvest festivals.
Here, Brunello is the attraction.
November also gives you a completely different Tuscany. The large summer crowds have disappeared, vineyards turn shades of gold and rust, fireplaces begin glowing inside restaurants, and Montalcino settles into a slower rhythm.
Add a glass of Brunello and we're perfectly happy.
What Is a Tuscany Wine Festival Really Like?
If you've never attended one, forget the image of a formal wine tasting.
Most Tuscan festivals are far more relaxed.
You will often purchase a festival wine glass—sometimes with a little pouch or strap that hangs around your neck—and then wander between tasting stations.
There is no need to be a wine expert.
Ask questions.
Tell the producer what you normally drink.
Ask what they recommend.
Ask where their vineyard is.
Ask whether you can visit their winery tomorrow.
Most importantly, don't feel like you have to rush from booth to booth trying everything.
You're in Tuscany.
Slow down.
The person pouring your wine may be the owner, winemaker or member of the family that has farmed the property for generations.
Give them time to tell you the story.
What to Eat at a Tuscany Wine Festival
Come hungry.
Depending on the festival and season, you might find:
pecorino cheese, prosciutto, salumi, crostini, porchetta, grilled meats, handmade pasta, ribollita, pappa al pomodoro, wild boar, truffle dishes and local desserts.
Autumn is especially good.
This is when Tuscany's wine festivals begin overlapping with the flavors of harvest season—mushrooms, chestnuts, truffles, olive oil and hearty Tuscan cooking.
One of our favorite approaches is simple:
Taste the wine being made in the region and eat whatever the locals are serving with it.
They've had a few centuries to figure out the pairing.
Are Tuscany Wine Festivals Good for Kids?
Many of them can be.
Festivals such as the Festa dell'Uva di Impruneta, Bravìo delle Botti and L'Eroica offer far more than wine tasting.
Parades, costumes, flag throwers, music, food, bicycles and historic streets give children plenty to see.
Calici di Stelle in Montepulciano has also included entertainment for children alongside its wine and food programming.
For families, we would generally choose one of these broader cultural festivals over an event primarily built around professional or concentrated wine tasting.
It gives the adults Tuscany's wine culture without making the children feel like they have been dragged to an enormous wine tasting.
Driving to a Tuscany Wine Festival
Here's the part nobody should ignore.
If you're tasting wine, have a transportation plan.
Many of these towns are easiest to reach by car, which creates an obvious problem when the entire reason for going is to drink wine.
If possible, stay in or near the town hosting the festival.
Walk.
Arrange a driver.
Use available festival transportation.
Or designate someone who isn't drinking.
Also expect parking to be very different during major festivals.
A quiet Tuscan village with plenty of parking on Tuesday morning can become an entirely different place when several thousand people arrive Saturday afternoon.
Get there early.
Where Should You Stay for Tuscany's Wine Festivals?
One of our favorite strategies is to turn the festival into the center of a larger winery trip.
For Greve, Panzano, Radda or Gaiole, stay somewhere in Chianti.
Better yet, stay at a winery castle or agriturismo.
For Montepulciano, staying around Montepulciano or the Val d'Orcia lets you combine the festival with wineries, Pienza, Monticchiello and some of Tuscany's most beautiful drives.
For Montalcino, stay around Montalcino and spend several days exploring Brunello wineries rather than making the festival a day trip.
This is where planning by region makes Tuscany much easier.
Instead of trying to see everything, choose one area and really experience it.
When Is the Best Time to Visit Tuscany for Wine Festivals?
If wine festivals are one of your priorities, there are three particularly interesting windows.
Late May — Wine Without the Harvest Crowds
Late May gives you events such as Radda nel Bicchiere and Cantine Aperte while Tuscany is still beautifully green.
The vineyards are growing, wildflowers remain in the countryside and summer heat hasn't fully arrived.
August — Summer Nights and Historic Traditions
August brings events such as Calici di Stelle and the Bravìo delle Botti.
It is hotter and busier, but Tuscany's towns come alive after sunset.
September Through Early October — Our Pick for the Full Wine Experience
For wine travelers, this is difficult to beat.
Expo Chianti Classico.
Vino al Vino.
Festa dell'Uva.
Harvest.
Cantine Aperte in Vendemmia.
L'Eroica.
And all around you, wineries are bringing grapes in from the vineyards.
This isn't merely wine tourism anymore.
You're watching the wine year reach its climax.
Don't Just Visit Tuscany's Wineries—Experience Tuscany's Wine Culture
A great winery visit introduces you to Tuscany's wine.
A great wine festival introduces you to the culture behind it.
The families.
The villages.
The food.
The vineyards.
The harvest.
The traditions.
And the people who have spent generations turning grapes grown on these hillsides into some of the world's most celebrated wines.
So if you discover that a wine festival happens to fall during your trip, make room for it.
Park the car.
Walk into town.
Grab a tasting glass.
Try something you've never tasted.
Talk to the person pouring it.
Eat whatever smells good.
Listen to the music.
And stay longer than you planned.
Because sometimes the best experiences in Tuscany are the ones that completely ruin your itinerary.
Tuscany Wine Festival Calendar at a Glance
Festival | Location | Typical Timing | Best For |
Radda nel Bicchiere | Radda in Chianti | Late May | Chianti Classico lovers |
Cantine Aperte | Wineries across Tuscany | Last weekend May | Visiting wineries |
Calici di Stelle | Montepulciano | August 10 | Wine under the stars |
Bravìo delle Botti | Montepulciano | Late August | Culture & families |
Expo Chianti Classico | Greve in Chianti | Second week September | Large Chianti tasting |
Vino al Vino | Panzano | Third weekend September | Meeting winemakers |
Festa dell'Uva Impruneta | Impruneta | Last Sunday September | Harvest traditions |
Festa dell'Uva e del Vino | Chiusi | Late September | Food, wine & local culture |
Cantine Aperte in Vendemmia | Wineries across Tuscany | Sept.–Oct. | Harvest experiences |
L'Eroica | Gaiole in Chianti | First weekend October | Wine-country atmosphere |
Benvenuto Brunello | Montalcino | November | Brunello enthusiasts |
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