Chianti Classico Itinerary – Unforgettable Via Chiantigiana

One of the most memorable road trips we made was through the winding Via Chiantigiana or the SR222 road, south of Florence on our way to Siena.  This is the land of the Gallo Nero, the symbol of the Consorzio Chianti Classico, the organization that protects the Chianti Classico wine and its trademark.  The region has a beautiful scenery, nature blends with small towns and ancient and historic buildings which have now been transformed into private villas or hotels. THIS is Chianti... Chianti Classico   Image Ladik

The itinerary along the S222 goes from Florence to Siena covering the villages of Greve in Chinati, Panzano in Chianti and Castellina in Chianti.  The surrounding villages of Gaiole in Chianti and Radda in Chinati are not too far away and also deserve a detour not only for the beauty of the landscape but also because the area concentrates large number of farms and wine cellars many of which offer tastings of their own wines. These are marked by roadside signs indicating “Degustazione” or “Wine Tasting”.

FLORENCE   The capital of Tuscany is without doubt one of the most beautiful cities I’ve visited, for its history, beauty, art and food.  There is so much to tell about this place that I prefer to  leave my impressions and recommendations for another moment and focus on the road trip to Siena.  The only thing I must  say is that whatever your itinerary, be sure to stay at least three days in Florence. From Florence we headed south to take Via Chiantigiana, the winding road crosses a region of hills planted with olive groves, cypresses and vines.  This is a land of ancient traditions and remote civilizations, first the Etruscans and then the Romans. The whole route to Siena is about 114km, 2 hours and a half, but since we stopped more than once to eat or sleep in the villages nearby, the trip ended up lasting four days. I don’t recommend this road at nighttime since it is dark and curvy.

Our first stop after 30km drive was Greve in Chianti. GREVE IN CHIANTI Greve is a very nice town for a stopover, it marks the first stage into the Chianti route to Siena.  Is a small wine-growing town, Saturday is market day and the main square gets crowded, people stroll along the pedestrian rcades, small restaurants and gardens and do their shopping and keep up with the latest gossips.


VIGNAMAGGIO   Via Petriolo 5 , Greve.   A Tuscan Historical Villa from the 14th century,  surrounded by vineyards and olive groves.  The rooms, suites and apartments are inside the villa and in the finely renovated farmhouses.

CASTELLO VICCHIOMAGGIO   Via Vicchiomaggio, 4 Greve in Chianti.  On the top of a hill, the castle dominates de whole Greve Valley.  Apartments are offered on a “self catering” basis, guests service their own room and prepare their meals if they decide to dine in. A maid service and breakfast are offered as options. Tastings and cooking classes are organised at the restaurant.  Rates from 147 Euros. Vignamaggio Vignamaggio  Image charley 1965


IL CAMINETTO DEL CHIANTI  Via della Montagnola, 52 – Strada in Chianti – Greve in Chianti.  Typical countryside restaurant for Sunday lunch. Tuscan cuisine, good value for money.

RISTORO DI LAMOLE    Via di Lamole, 6, Lamole – 8km from Greve in Chianti.  A typical trattoria in the middle of the Chianti area. The environment is very simple and genuine with a beautiful terrace that overlooks the best vineyards of the Chianti Classico.  First courses vary according to season.Ristoro di Lamole Ristoro di Lamole  Image senza senso


MUSEO DI SAN FRANCESCO  Was opened September 7, 2002, in the former convent of San Francisco.  In the museum, which is on two levels, are works of art from the territory.

CASTLE TOWN OF MONTEFIORALLE   The village of Montefioralle is one of the most well-preserved medieval villages in all of Tuscany. Originally a walled castle, Montefioralle  is an easy 20 minute up-hill walk or a short car ride from Greve.


PANZANO IN CHIANTI Panzano in Chianti is just 10km south of Greve.  Panzano is a town that developed around a castle, like many in this region. Is situated on a hill and  the first thing you will see as you approach the village is the castle and clock tower. The castle is private, but you can visit the courtyard and surrounding area. Panzano’s churches worth a visit, the church of Santa Maria Assunta stands next to the castle.  Planning ahead would be interesting to match any of the festivals that take place in the village.  Every Sunday morning there is a market on the main square, until 1p.m.


VILLA ROSA DI BOSCOROTONDO Via S. Leolino 59, Panzano.  Villa Rosa di Boscorotondo is a small country resort, has rooms with private bath, a swimming pool and cooking classes are available upon request. Rates from 80 Euros.

VILLA LE BARONE   Via San Leolino 19, Panzano in Chianti.  A romantic 3 star hotel set above the hills, built in the Renaissance.  Has 28 rooms, swimming pool and a large terrace surrounded by rose gardens, the perfect place to  enjoy splendid views of the vineyards, olive groves and hills nearby.  B&B from 190 Euros, in low season.                                Image Villa le Barone

eat & wine tasting

VILLA CAFAGGIO  5 v. S. Martino A Cecione, on the Strada Provinziale 118, 4km north of Panzano.  The ancient Villa Cafaggio estate in Panzano is considered one of the best producers of Chianti Classico. It ‘s always possible to buy products directly from the farm Villa Cafaggio. The time of resale to the public from Monday to Friday from 10.00 to 18.00.  The visits are available every day from Monday to Saturday by appointment.

CENNATOIO   Via S.Leolino, 35 is a commercial farm, that produces wine and spirits, typical Tuscan products and delicatessen.  The premium vineyards at Cennatoio, separated by olive orchards, cover a total of 10 hectares, marking an appointment you can taste wines and visit the cellar.

ANTICA MACELLERIA CECCHINI Via XX Luglio, 11 Panzano in Chianti.  The owner Dario Cecchini is an excellent cook and showman. His shop is a tourist attraction as well as a place to buy unusual cuts of fresh meat and prepared meats.  The bistecca alla fiorentina (Florentine-style T-bone steak) is the signature dish of this creative butcher. Dario Dario Cecchini   Image pikimota

CASTELLINA IN CHIANTI 15km south of Panzano is the medieval village of Castellina in Chianti.  Castellina is at a dream crossroads.  To the south lies Siena, to the north, Florence, to the east, Radda in Chianti and Gaiole in Chianti, to the west, San Gimignano and Colle Val d’Elsa.  It is almost impossible to choose which way to go.  I suggest to set base in Castellina and devote two or three days to discover the area.  The town has incredible views, very good restaurants, small shops and wine .


CAPOVENTO   Via della Badiola – Loc. Capovento, Castellina in Chianti. Lovely place to stay.  Rates from, 120 Euros for a standard room, low season, breakfast included.

BADIA A COLTIBUONO  Gaiole in Chianti.  A former monastery is now a family run estate, offering accommodation, restaurant and cooking courses.

LA PETRAIA     Radda in Chianti, 12 minutes from Castellina in Chianti.  La Petraia is a highly recommended classic Tuscan farmhouse.  The main building at La Petraia has four guest rooms, a kitchen and a dining room.  Rates from 200 Euros per person, breakfast and dinner included. Image La Petraia


ANTICA TRATTORIA LA TORRE  Piazza del Comune  15, Castellina in Chianti.  Piazza del Comune, opposite the church.  The family Stiaccini, is engaged in the food and catering for over a century.  The ingredients of their basic dishes, are the typical products of the earth: Chiantigiana wine, olive oil, poultry, game, sheep, pork and cow, grains, beans and mushrooms.

ALBERGACCIO DI CASTELLINA  Via Fiorentina, 63.  An old stone barn, a few tables for only 30 seats with a stylish equipment and specialties as Florentine steaks, grilled meats, Chianina beef, homemade pasta. L’Albergaccio di Castellina


BROLIO CASTLE  Originally built in  the thirteenth century, is one of the most famous inhabited castles in Tuscany.  The ramparts and the gardens may be visited without charge, the castle also offers a paid historical tour which includes the gardens and the museum, and a paid wine tour which includes a wine tasting. The interior apartments of the castle are not open to the public. VIA FERRUCCIO  Is the main street of Castellina, home to the Palazzo Ugolini and Palazzo Biancardi. Via Ferruccio, Castellina in Chianti

side trips

RADDA IN CHIANTI   Is a beautiful medieval town enclosed in large defensive walls. Located up on a hill between the valleys of Arbia and Pesa, it has ancient origins.

CASTELO DI VOLPAIA   Loc. Volpaia-Coltassala Radda in Chianti.  Is not just a wine estate but a small village with a wine shop, restaurant, accommodations for rent. Volpaia Volpaia  Image  fondelli.nadia


2 thoughts on “Chianti Classico Itinerary – Unforgettable Via Chiantigiana

    1. How do I do this beautiful itinerary without a car? (Proposed travel in September 2016 for one person)?


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