We’ve been living in the Chianti area, and loving it, for a few years now. So we’d like to suggest an itinerary that shows off this charmingly rural and wonderfully scenic, part of Tuscany. This road trip is easily organised if you’re based in (or near) Florence. It takes in the small towns of Montespertoli, San Casciano Val di Pesa and Certaldo, passing through beautiful hamlets and picturesque spots (get your camera ready!). And needless to say, this area is famed for its red wines, so there’re plenty of opportunities to please both the eyes and the palate.

In recent years travellers have been discovering this area, choosing it over the better-known (and busier) Chianti Classico region, with the justly famous Greve and Radda in Chianti.

A Scenic Itinerary Off-the-Beaten- Track in the Chianti, central Tuscany

Our itinerary starts in San Casciano Val di Pesa – the historic small town, gateway to the Chianti region – and ends right at the heart of the Val d’Elsa, in the picturesque hilltop town of Certaldo Alto. You could say that the major sight here is the landscape, a soothing continuum of vineyards, silvery olive groves, wavy hills where beautiful farmhouses sit quietly flanked by cypress trees. The occasional castle or country church completes the scene.

Duration of the Itinerary: 1 day. Total length => 40 km. Allow one full day to enjoy this road trip. Don’t rush, forget major sightseeing and embrace the spirit of Tuscany! (20 km. from San Casciano to Montespertoli – 20 km. from Montespertoli to Certaldo).

San Casciano in Val di Pesa

San Casciano has made it onto the tourist maps in the last few years. Conveniently located 18 Kms. south of Florence, it’s the preferred choice for anyone looking for an authentically Tuscan (and crowd-free) experience. It has one small art museum, and various shops to keep you entertained for at least a couple of hours. The Trattoria Cantinetta del Nonno, is a great spot for lunch (and a personal favourite) for a traditional meal at very reasonable prices.

Detour => Wine lovers might want to check out the Cantine Antinori, a superbly designed winery a few kms. from San Casciano, at Bargino, where you also find an exceptional fish restaurant, La Trattoria del Pesce.

TOP WINE TASTING CHIANTI EXPERIENCE => Visit two Chianti Wineries and their cellars to learn about the production methods of Chianti Classico wine. Beautiful scenery and a Tuscan-style lunch paired (of course!) with local wine.

=> Top 10 Experiences for Wine Lovers in Tuscany

From San Casciano to the ‘wine town’ Montespertoli

Driving along SP12, surrounded by picture-perfect views of beautifully kept vineyards and olive groves, you reach Cerbaia (the only reason to stop here is the Bar Pasticceria Pimpina for a croissant and a cappuccino, the best in the area), and then you take the SP4 Via Volterrana to Montespertoli. On the way, you’ll pass Montegufoni Castle, an impressive structure dating back to the Middle Ages, today an agriturismo hidden among tall fir and cypress trees.

The Via Volterrana (that links Florence to Volterra), was once a strategic road used for transporting salt and minerals from Volterra, and many noble families chose this area to built their castles and villas. Right at the entrance of the town, there’s Castello Sonnino, once a mighty castle, now a great spot to buy some local Chianti wine (If you’d like to have a tour and do some wine tasting you need to book in advance).

Montespertoli is a quiet town with two beautiful squares, Piazza Machiavelli – with the Church of Sant’Andrea and a lovely building with two clocktowers – and the largest Piazza del Popolo, surrounded by shops. Montespertoli prides itself on its excellent olive oil and above all, its wine (at the entrance of the town there’s a sign that names it “città del vino“), and every year at the end of May hosts the Mostra del Chianti di Montespertoli ,where local producers come to showcase their vintages. The town might look a bit sleepy to some, but the scenic views all around it are definitely worth the trip.

Detour => In the Medieval hamlet of Lucardo, the original settlement that later became Montespertoli, you find the exquisite Romanesque Church of San Piero in Mercato, with a small Sacred Art Museum.

less travelled chianti itinerary

From Montespertoli to Certaldo Alto

Along the road SP79, you’ll drive through the tiny hamlet of Fiano and, if you’re travelling in Summer, an expanse of sunflowers on a flat stretch of road that leads to Certaldo.

The last stop in our itinerary is charming Certaldo Alto, a hilltop town famous in Tuscany for being the place where the Medieval poet Boccaccio was from. And you could say that the Middle Ages have never completely left this wonderfully preserved historic town. Some of the edifices have been restructured, keeping the medieval architecture in mind, like the crenellated walls of the Palazzo Pretorio.

As for sightseeing, Certaldo is the highlight of our itinerary. You can get a combined ticket to visit the Boccaccio Tower House – climb to the top for the best view! – the Palazzo Pretorio, and the small Sacred Art Museum. Don’t forget to pay homage to Boccaccio in the SS. Iacopo e Filippo Church where he’s buried. A choice of traditional trattorie and restaurants, in the historic centre and in the low new of town, make this town a real treat.

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Certaldo Alto

Different seasons, different colours

In Spring you’ll enjoy all the colours of wild flowers, poppies, wisteria, roses, irises, and the countryside at its greenest. In Summer the landscape changes to hues of burned yellow, by August the fields looks quite dry, while the vines are getting ready for September grape harvest. The road to Certaldo is flanked by sunflower fields that give their best in July. If you’re travelling in Summer, keep in mind that temperatures can get quite high in July and August (35C and over).

In Autumn the vineyards turn orange and yellow, and the countryside is simply lovely, with the first fire being lit and the olive picking at the beginning of November. Winter is quieter and the countryside shows its less verdant side.

Less Travelled Chianti Itinerary – Practical Tips

Remember that in many small towns around Tuscany shops close between 1pm to 4/5 pm.

From 1st November to 31st March sights in Certaldo are open on a reduced time (from monday to friday 10am-1pm and 2.30-4.30pm, saturday and sunday 10am-1pm and 2.30-5.30pm, closed on tuesday). Rest of the year: 10am-1pm and 2.30-7pm.

Parking: San Casciano and Montespertoli have parking spaces just outside the town centre. In Certaldo you leave the car in the new part of town (Certaldo Basso), and reach the historic centre on top the hill either walking (it takes around 15 minutes, and is pretty steep) or take the funicular railway from Piazza Boccaccio, that runs every 15 minutes.

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