Do you recall those wonderful postcard landscapes of Tuscany with rolling hills topped by ancient villages? The wonderful sunflowers, the fine vineyards, the olive groves, and the winding streets marked by rows of cypress trees? This is the Chianti area between Florence and Siena that boasts some of the most beautiful landscapes in the world. Follow us along the most beautiful roads of Chianti from Florence to Siena discovering lovely views, perfectly preserved medieval villages, and savory foods you will not soon forget.
Wander from Florence to Siena via Italy’s most picturesque routes to discover fascinating medieval villages while sampling Tuscany’s mouth-watering foods
Chianina, the real Florentine T-bo
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Let’s start from Florence. You can’t miss an appointment with the Bistecca alla Fiorentina (the Florentine T-bone).
The original recipe dating back to Medici family times calls for loin of Chianina beef with the T-shaped bone in the middle, 1.5 kg weight and 5-6 cm height, cooked rare, grilled only with burning wood. Following are our favorite places to try Bistecca, strategically close to the must-see destinations. Leave from the Uffizi Gallery take Via dei Neri for about 300 meters, passing by typical shops up to Corso dei Tintori 47r where you will find Il Fagioli. At this highly rated restaurant they prepare an especially delicious Fiorentina with stuffed pasta (plus, you’ll be a stone’s throw from Piazza Santa Croce!).
Very close to the Accademia Gallery, where the David by Michelangelois hosted, visit the Ristorante Accademia (Piazza San Marco 7r). In addition to steak, they also have an excellent tasting menu! If you are near the Duomo eat at Il Latini located at Via Palchetti 6r.
To find the best red and white Tuscan wines try the Private Wine Tasting Tour.
For a full immersion in the delicacies of Florence try the Gastronomic tour of Florence, which includes a visit to the picturesque San Lorenzo market!
The Florentine Chianti
Chianti is famous all over the world for its quality wine, but there’s much more! The area is waiting to be discovered along scenic roads surrounded by greenery,vineyards, and farms– often open for tastings – and small villages where time has stopped.
An especially interesting route goes south from Florence, with a first stop at Impruneta (20 km from Florence downtown), a small village famous for its pottery and the Sanctuary of Saint Mary. Try the Trattoria Di Gazzilloro (Via Roma 19) with homemade pasta in an intimate setting. A great way to discover this area is to try the Oil, Cheese and Wine tour in Impruneta and Chianti.
Then, continue towards San Casciano in Val di Pesa, famous for its ancient churches, medieval castles and villas overlooking the beautiful valleys. Do not miss a stop at the restaurant Cinque Di Vino (Via San Francesco 32) for truffles and mushrooms.
The road to Panzano and Greve in Chianti is one of the most beautiful in Tuscany. Greve hosts a scenic square, with the agricultural market and the historical Falorni butcher’s shop where you can taste the best hams, sausages and cheeses in Tuscany. Keep exploring up to Radda and Gaiole in Chianti. The Castle of Baron Ricasoli Brolio will amaze you with its architecture, location, and tasty products! If you prefer to be guided, join our Private Tour of the Chianti Classico Area, or for an immersion into nature discover Chianti by horse!
Flavors of the Middle Ages
Heading south on the Provincial Road 1 from Poggibonsi, you will reach San Gimignanoin 15 minutes. It is the best-preserved medieval village in Tuscany and is a UNESCO heritage site. Twenty-five of its original 72 stone towers are still standing.
Follow its narrow streets to the squares of the Duomoand La Cisterna, where you will find the Gelateria Dondoli, winner of the gelato World Championship with amazing flavors including saffron and pine nuts! Climb up to theRocca di Montestaffoli for a stunning panorama of the Chianti. Taste the local delicacies at La Mangiatoia (the Manger, at Via Mainardi 5) with its romantic ambience and delightful cuisine including Pici Senesi and chocolate cakes. You can easily reach this magic village directly from Florence by joining our Tour of San Gimignano and Monteriggioni, another small pearl of Chianti.
Continue on SR68, >one of the most scenic roads of Italy with views of the most famous picture postcard landscapes. Arrive in about half an hour at Volterra, a wonderful village full of history, with Etruscan and Roman archaeological remains and a medieval heart at Palazzo dei Priori. Artisans of this city specialize in alabaster crafts, and their cuisine offers strong flavors such as wild boar and truffles. Try them at the Osteria La Pace (Via Don Minzoni 55).
If you don’t feel comfortable following this itinerary on your own, join our Essence of Tuscany tour, a full day of unforgettable experiences that will take you to many of these places, following the Via Francigena up to the scenic Val d’Orcia and Montalcino, famous for itsBrunello. If you love this icon of Italian wine, try our Montalcino and Brunello Tour for an extraordinary experience that will take you through the vineyards and into the cellars of the best producers.
The Crete Senesi
We are almost in Siena, an extraordinary city that deserves a full day to stroll the streets and its medieval heart,the Piazza del Campo with its Civic Museum and the Cathedral.
The Duomo is as beautiful and rich as that of Florence: visit it with the advantageous OPA SI Pass. Departing from Siena, follow the itinerary through the Crete, an amazing area with stunning landscapes.
Reach the hamlet of Arbiaand take the Strada Statale Lauretana for 30 kilometers out of this world”, in heartbreakingly beautiful – almost lunar – landscapes filled with farms producing delicious pecorino sheep cheeses plus holiday farmhouses. At Asciano try Lo Scudiero (Corso Matteotti 138) for its memorable pici and baked cheese! Follow the brown signs that indicate the strade bianche (unpaved white roads). You will literally pass through the fields, with unique views for observing nature at its stunning best.