Discover the most iconic villages of the Chianti Classico region on a tour taking in vineyards, wineries, breathtaking views and the authentic flavours of Tuscany.
A day in the heart of Tuscany
If you’re planning a trip to the Chianti Classico area and wondering what to see in Greve in Chianti, Panzano in Chianti, Castellina in Chianti and San Gimignano, you’ve come to the right place.
These four villages embody the very essence of Tuscany: hills covered in vineyards, cypress trees, medieval castles, culinary delights and picture-postcard views. As they are so close together, you can visit them all in a single day, enjoying an authentic experience steeped in wine, art, history and traditions.
If you’re staying at Le Filigare Wine & Country Relais, you’ll be in an ideal location from which to set off and explore these iconic places.
Map of the route
Le Filigare → Greve in Chianti → Panzano in Chianti → Castellina in Chianti → San Gimignano → Le Filigare
Total journey time: approximately 1 hour and 30 minutes
Recommended duration: full day (9.00 am – 8.00 pm)
1. Greve in Chianti: the heart of Chianti Classico
The day begins in Greve in Chianti, considered the gateway to the Chianti Classico region.
The historic centre is centred on the famous Piazza Matteotti, a triangular square lined with arcades and surrounded by artisan workshops, wine bars, cafés and shops selling local specialities. It is the ideal place to soak up the relaxed atmosphere of Chianti, strolling amongst historic buildings and sampling the finest local produce.
Not to be missed
- Piazza Matteotti
- Church of Santa Croce
- Traditional craft workshops
- Wine bars in the historic centre
- Shopping for extra virgin olive oil and local specialities
Recommended panoramic view
Before leaving Greve, take the scenic road towards Panzano: the viewpoints along the way offer some of the most iconic views of the Chianti Classico region.
Where to have breakfast
- Caffè Le Logge – excellent for cappuccino and handmade pastries.
- Enoteca Falorni Wine Bar – the perfect place to start the day with a tasting of local produce.
2. Panzano in Chianti: the village overlooking the Conca d’Oro
Just ten minutes from Greve lies Panzano in Chianti, one of the most charming villages in the area.
The village overlooks the spectacular Conca d’Oro, a natural amphitheatre of vineyards that is one of the most photographed landscapes in Tuscany.
As you stroll through the streets of the village, you’ll discover an authentic atmosphere, with its small art galleries, shops, wine bars and panoramic views.
Places to visit
- Piazza Bucciarelli
- Medieval Old Town
- Church of Santa Maria Assunta
- Viewpoint overlooking the Conca d’Oro
Where to have lunch
For meat lovers:
- Dario Cecchini’s Officina della Bistecca
Or:
- Solociccia
- Osteria Le Panzanelle (just a few minutes from the town centre)
3. Castellina in Chianti: a blend of history and medieval walls
In the afternoon, head to Castellina in Chianti, one of Tuscany’s best-preserved medieval villages.
Its most famous attraction is the Via delle Volte, a picturesque covered walkway built within the ancient castle walls.
A stroll here is like stepping back in time, amidst stone buildings, medieval arches and views that open out onto the Chianti hills.
Places to visit
- Via delle Volte
- Rocca di Castellina
- Chianti Archaeological Museum
- Old Town
Panoramic view
From the Rocca, you can enjoy one of the most beautiful views of the Chianti Classico hills.
Where to stay
- Bar Italia
- Taverna Squarcialupi
- Tre Porte
4. San Gimignano: the Manhattan of the Middle Ages
Round off the day with a visit to San Gimignano, a UNESCO World Heritage Site and one of Italy’s most famous medieval villages.
Its stone towers dominate the Tuscan landscape and create a unique atmosphere, especially in the late afternoon when the sunlight illuminates the medieval façades.
Places to visit
- Piazza della Cisterna
- Piazza del Duomo
- Duomo di San Gimignano
- Torre Grossa
- Rocca di Montestaffoli
The advice
If you arrive after 5.00 pm, many organised groups will have started to leave the village, and you’ll be able to enjoy the medieval streets in a much more peaceful atmosphere.
Where to eat
- Cum Quibus
- La Mandragola
- Perucà
- Gelateria Dondoli, which has been recognised on numerous occasions as one of the world’s best ice-cream parlours.
Le Filigare: the ideal starting point
After a day spent exploring some of Tuscany’s most beautiful villages, there’s nothing better than returning to the vineyards of Le Filigare Wine & Country Relais.
Situated in the heart of the Chianti Classico region, the estate is the ideal base from which to explore Greve, Panzano, Castellina and San Gimignano without having to travel far.
Here, guests can relax surrounded by nature, sample the organic wines produced on the estate and experience authentic Tuscan hospitality.
Useful tips
✔️ Set off by 9.00 am.
✔️ Book restaurants and tastings in advance, especially from April to October.
✔️ Wear comfortable shoes: the historic centres are almost entirely paved with stone.
✔️ Take a camera with you: every stop offers unforgettable panoramic views.
✔️ If possible, visit San Gimignano in the late afternoon to avoid the busiest times.
Why this itinerary is special
In just one day, you can experience everything that makes Chianti one of the world’s most beloved destinations: perfectly preserved medieval villages, centuries-old vineyards, culinary delights, iconic wines and landscapes that look as though they’ve stepped out of a painting.
Whether you’re a wine enthusiast, a photography lover or simply looking to experience the real Tuscany, this itinerary will allow you to discover the best of Chianti Classico, starting from Le Filigare.
