When people picture Tuscany, they are usually imagining Chianti.
Rolling vineyards stitched together by winding roads. Stone farmhouses perched atop hills. Medieval villages crowned with church towers. Long lunches under the shade of olive trees accompanied by glasses of Chianti Classico.
After exploring the dramatic landscapes of Val d’Orcia, we headed north into the heart of Chianti, one of Tuscany’s most beloved wine regions. For several days, we based ourselves at Il Borgo di Vescine, a beautifully restored medieval village near Radda in Chianti, and spent our days discovering charming towns, scenic drives, vineyards, and some of Tuscany’s most iconic destinations.
Some villages immediately won us over with their authenticity and relaxed atmosphere. Others dazzled with postcard-perfect views. And one of Tuscany’s most famous towns left us feeling that it was beautiful… but perhaps a little too polished for our taste.
If you’re planning a Tuscany road trip, here’s how we explored Chianti from our base in the heart of wine country.
WHAT IS IN THIS POST
Black rooster: The Symbol of Chianti
You will find a large, black rooster at the entrance of many of the towns in Chianti include a sculpture of a rooster in Gaiole in Chianti… and also featured in shops and restaurants in town.
The rooster is the symbol of the Chianti League (Lega del Chianti), which includes Radda in Chianti, Gaiole in Chianti and Castellina in Chianti. The League’s members were allies and worked to defend the Florentine territory.
This is why you see the black rooster on the necks of bottles of Chianti Classico wines. It’s the symbol of Chianti.
Why Stay at Il Borgo di Vescine?
Finding the right base can completely shape your Tuscany experience, and Il Borgo di Vescine turned out to be one of our favorite stays in Italy.
Nestled among vineyards and olive groves just outside Radda in Chianti, the property feels less like a hotel and more like a tiny medieval village that has been lovingly preserved. Stone buildings draped in ivy, narrow pathways, flower-filled courtyards, and sweeping vineyard views create an atmosphere that feels quintessentially Tuscan.
Each morning we enjoyed breakfast overlooking the countryside before setting off to explore nearby villages. Evenings were spent lingering over dinner and watching the golden light settle across the vineyards.
Its central location made it easy to visit all of Chianti’s major towns while returning each night to a peaceful countryside retreat.
If you’re looking for a romantic place to stay in Chianti, this is hard to beat.
Discovering Radda in Chianti
Before venturing farther afield, spend some time exploring Radda itself.
Often considered the heart of the Chianti Classico region, Radda is everything we hoped a Tuscan village would be. Historic stone buildings, small wine bars, local shops, and quiet piazzas create an atmosphere that feels authentic rather than tourist-driven.
Protected by medieval walls and surrounded by vineyards, Radda remains wonderfully walkable. It isn’t packed with tour buses or large groups. Instead, visitors linger over meals, browse local wine shops, and enjoy the slower pace of life.
Of all the towns we visited in Chianti, Radda felt the most balanced… a place that welcomes visitors while still maintaining its local character.
Castellina in Chianti
A short drive from Radda brings you to Castellina in Chianti, another charming hill town with deep roots in the region’s history.
Its most distinctive feature is the Via delle Volte, a covered medieval walkway that runs beneath ancient fortifications and offers glimpses of the surrounding countryside.
The town itself is compact and easy to explore, with cafés, artisan shops, and viewpoints overlooking vineyards and olive groves.
Castellina felt lively but not overcrowded and quickly became one of our favorite stops.
Gaiole in Chianti
While many visitors focus on Greve and San Gimignano, Gaiole deserves far more attention than it receives.
The village itself is small, but the surrounding countryside is spectacular. Some of the most beautiful drives in Chianti begin here, winding through vineyards, forests, and historic wine estates.
This is the Chianti of postcards and travel dreams.
We found ourselves stopping frequently along the roads simply to admire the scenery. Around every bend seemed to be another vineyard, stone farmhouse, or cypress-lined driveway.
For wine lovers, this area is especially rewarding, with many renowned wineries nearby.
Panzano in Chianti
Panzano may have offered some of the most spectacular views of our entire trip.
Perched high above the surrounding countryside, the village enjoys panoramic vistas across vineyards that stretch toward the horizon.
Unlike some of Tuscany’s larger destinations, Panzano still feels wonderfully local. The pace is slower, the streets quieter, and the atmosphere more relaxed.
It’s the kind of place where a quick stop easily turns into a leisurely afternoon.
We wandered through the historic center, paused for coffee, admired the views, and simply enjoyed being there.
Greve in Chianti
Greve is often considered the gateway to Chianti.
Its large triangular piazza, Piazza Matteotti, immediately sets it apart from neighboring villages and serves as the social heart of the town.
Compared to Radda and Panzano, Greve feels more commercial and more geared toward visitors, but it still retains plenty of charm.
Wine shops, restaurants, and local markets create a lively atmosphere, making it an excellent stop for lunch or an afternoon stroll.
If you’re looking to bring home local wine, olive oil, or Tuscan specialties like ceramics, Greve is a great place to browse.
Cycling in Chianti
Rent a bike from one of shops in town of Chianti and you can go on your own self-guided adventure on the trails and open road of the Chianti Hills. We saw many cyclists when we driving around to the little villages and spoke to a couple from Canada who come every year to ride their bikes here.
Another fun thing to do in Chianti is renting a scooter to zip around it. The roads here much easier to navigate compared to the Amalfi coast.
A Day Trip to Siena
One of the advantages of staying in Chianti is how easily you can reach Siena.
Of all Tuscany’s cities, Siena may be the most captivating.
Its narrow streets, medieval architecture, and rich history create an atmosphere unlike anywhere else in the region. The city eventually unfolds into Piazza del Campo, one of Italy’s most extraordinary public squares.
We spent hours wandering Siena’s labyrinth of streets, discovering hidden courtyards, churches, and viewpoints.
Despite its popularity, Siena still feels like a living city rather than a destination created solely for tourists.
The scale, beauty, and history make it one of Tuscany’s essential experiences.
If you only have time for one day trip from Chianti, make it Siena.
San Gimignano: Beautiful but Overrun
Few places in Tuscany are as instantly recognizable as San Gimignano.
Its medieval towers rise dramatically above the countryside, creating one of Italy’s most iconic skylines. Known as the “Medieval Manhattan,” the town is undeniably beautiful and photogenic.
And yet, San Gimignano was probably the place where we felt the most disconnected from authentic Tuscany.
By late morning, the narrow streets were filled with tour groups following guides carrying brightly colored flags. Souvenir shops lined many of the streets, and the atmosphere felt far more commercial than anywhere else we visited.
At times it reminded me of a beautifully preserved movie set… impressive to look at but lacking some of the lived-in charm we found elsewhere.
That’s not to say it isn’t worth visiting. The architecture is remarkable, and seeing those famous towers up close is unforgettable.
But after spending time in places like Radda, Panzano, and Gaiole, San Gimignano felt more like a destination designed around tourism than a town shaped by everyday life.
If you decide to visit, arrive early in the morning or stay later in the evening. You’ll experience a quieter and far more enjoyable version of the town.
Photos from our stay at Il Borgo di Vescine and dinner in the olive grove
The Scenic Drives Are the Real Highlight
As much as we enjoyed visiting the villages, some of our favorite moments happened on the roads connecting them.
The drives between Radda, Castellina, Gaiole, Panzano, and Greve are among the most beautiful in Tuscany.
Vineyards ripple across hillsides. Olive groves blanket the landscape. Cypress trees punctuate the horizon. Medieval villages appear in the distance like scenes from a Renaissance painting.
The scenery changes with every season, but the beauty remains constant.
In Chianti, the drive itself becomes part of the experience.
Food, Wine, and the Chianti Lifestyle
One of the greatest pleasures of visiting Chianti is embracing the slower pace of life.
Days revolve around long lunches, wine tastings, leisurely drives, and evenings spent outdoors.
Some highlights included:
- Chianti Classico wine tastings
- Handmade pici and fresh pasta
- Florentine steak
- Truffle dishes
- Local olive oils
- Vineyard lunches with sweeping countryside views
The region rewards travelers who slow down and savor each experience.
How Many Days Do You Need in Chianti?
While many visitors experience Chianti as a day trip from Florence, I recommend spending at least three to four days in the region.
Staying in the countryside allows you to enjoy the quiet mornings, scenic drives, vineyard sunsets, and village life that day-trippers often miss.
Using Il Borgo di Vescine as a base, we never felt rushed and had plenty of time to explore both famous destinations and lesser-known villages.
Final Thoughts on Exploring Chianti
Looking back, what stays with me most isn’t a single winery or landmark. It’s this photo we took on the way to a winery. It somehow captures the feeling of Chianti.
The golden light spilling across vineyards at sunset. The winding roads leading from one medieval village to another. The leisurely lunches, the glasses of wine shared outdoors, and the simple joy of slowing down.
While Siena impressed us with its grandeur and San Gimignano dazzled with its famous towers, it was the smaller villages of Radda, Panzano, Castellina, and Gaiole… that captured our hearts.
They felt authentic, welcoming, and deeply connected to the landscape around them.
If you’re planning a Tuscany itinerary, don’t rush through Chianti. Stay a few days, choose a beautiful countryside base, and allow yourself to wander.
The most memorable experiences often happen between the famous stops.
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