Published on: 9 February 2014 | Last updated: 9 February 2018
A classic ride through the Chianti wine country (this is the area where Chianti Classico is produced) following the Via Chiantigiana (SR222) before turning off towards San Gimignano - a medieval Manhattan. San Gimignano if famous for its towers - like medieval Manhattan (if Manhattan had been built on a hill). Your first sight of the towers of San Gimignano on the horizon will be a memorable moment. The town is on UNESCO's list of World Heritage sites (UNESCO's reasons). At the height of its glory the city must have been a truly amazing site: the 14 towers that we see today are only a fraction of the original 72.
There's quite a lot of climbing but the views definitely repay the effort. The best time to go is early autumn as the leaves in the vineyards are changing colour from green to gold, orange and red. If you're in a hurry you could continue along the Via Chiantigiana direct to Siena.
Map and altitude profile
Powered by WP-GPX Maps
tips for using the map
Run your cursor over the graph to show the elevation, and distance from the start, for any given point on the route. (Note: the altitude graph is not shown where the route is flat).
Click the little icon in the right-hand corner to see the map fullscreen
The first challenge is getting out of Firenze and over the A2 autostrada. The route suggested here is the way I went, which involves a bit of a detour via Bagno a Ripoli and from there following the Strada Comunale Ritortoli as it starts to climb into the hills. There are other more direct options, but like most of the routes I've taken into and out of Firenze they involve narrow roads between high walls and no pavement - which personally I find a bit unnerving.
The aim is to pick up the Via Chiantigiana on the outskirts of Firenze near Ponte a Ema, just before it goes under the motorway. From here you continue through Grassina which is really still a suburb of Firenze, before starting to climb into the hills on towards Strada-in-Chianti and then on to Greve-in-Chianti.
Greve-in-Chianti: home of two of the great navigators
You'll see the Castello da Verrazzano a few kilometres before reaching Greve. The castello (castle) was the birthplace of Giovanni da Verrazzano, the explorer who discovered the Hudson Bay and who was born just to the north of Greve (see verrazzano.org for more about his. There's a statue of the explorer in the main Piazza Matteotti. The piazza, with a portico on three sides with artisan shops, workshops and restaurants is worth the detour. Look out for the Antica Macelleria Falorni a butcher's shop that's been on the piazza since 1729.
From Greve you could go in search of another great Italian navigator Amerigo Vespucci who is thought to have been born in nearby Montefioralle, a fortified village a couple of kilometres and a bit of a climb away. The Vespucci family home is in the main street - the house is identified by a V and a wasp (vespa is the Italian word for wasp).
Panzano in Chianti and 'the world's most famous butcher'
The next village along is Panzano in Chianti. Panzano is home to celerity butcher Dario Cecchini who runs another antica macelleria. He has been described by the International Herald Tribune as the world's most famous butcher (although of course you have to wonder how many other famous butchers there are in the world). The village is a bit of a mecca for foodies - or at least a meat-eating foodies. There's a good article and interview on independent.co.uk and other articles on girlinflorence.com, and divingandtravelling.com.
More about Dario Cecchini
I have to admit that I passed through Panzano (twice) without knowing anything about him, and initially I was a bit sceptical, but watching this video, I started to be won over. Dario Cecchini 'Carne e Spirito'
The video is a 26-minute talk he gave in Copenhagen. His argument is basically that if we are to eat meat we should value it and make use of every part of the animal: as he explains, growing up as the child of a butcher he lived on the cuts no one else wanted to buy. The talk is in Italian but with translation (by his American wife). It's not for the squeamish though. It ends with him declaiming a stanza or two of Dante and a Shakespeare-related pun.
If you're curious you can also read Heat: An Amateur's Adventures as Kitchen Slave, Line Cook, Pasta-maker and Apprentice to a Butcher in Tuscany by Bill Buford and enjoyable account of his time with Cecchini in Panzano. It is also offers some interesting insights into the area.
You could pay 200€ to be a Macellaio per un giorno - butcher for the day.
Cecchini has three restaurants in the town, with the cheapest, is Dario Doc which offers the Mac Dario, burger menu at 10€. Just to prove that the to beef or not to beef line was not a flash in the pan there's a Super Dario menu at 15€). (Open lunchtimes only Mon-Sat). Just in case you're wondering, they also do a vegetarian menu. The other restaurants in the village are Solociccia and Officina della Bistecca.
After Panzano comes the Conca d'Oro - the bowl of gold. The name comes from the fact that this was once a wheat-growing area. Now, it is dominated by vineyards. The route goes down into the bowl and at the ridge over the Fiume Pesa (river Pesa), you have the choice of turning off and heading towards San Gimigano, or starting the climb towards Castellina-in-Chianti.
If you are heading for San Gimignano you need to turn off the Via Chiantigiana, just after it crosses the Fiume Pesa (river Pesa) - about 40 kilometres out of Firenze. If you are planning to continue to Siena you stay on the road for the route description read the next part of the series The Heart of Toscana: Firenze - Siena direct.
There are a couple of short climbs before the route crosses the motorway and another short climb to Tavernelle Val d'Elsa (381m) - the highest point on this section. From here there's a short section of relatively busy road before the turning of just after Barberino Val d'Elsa. Barberino Val d'Elsa is easy to miss (I did) but again, it's worth a quick detour if you have time.
After Barberino there's a long cruisey descent down towards Certaldo in the valley. Again the road will take you past the centro storico if you let it - you can see the old part of town on a small rise. The route then crosses the main Via Cassia which, at this point, is pretty horrible - it seems to be a cut-through for lorries. Fortunately you only have to get across it.
After crossing the road the route climbs on very quiet roads through vineyards and olive groves towards San Gimignano. San Gimignano is surrounded by vineyards: unusually for Toscana the leading wine is a white wine: Vernaccia di San Gimignano. Look out for the city on the skyline. The first sight of it should be an unforgettable moment.
If you don't do anything else in San Gimignano, climb the Torre Grossa ('Big Tower') (opening times and prices) part of the Palazzo Comunale and the nearby Piazza della Cisterna. There's a nice gallery of images taken from the tower on stretchingintoinfinity.com
There's also the Capella di Santa Fina in the Chiesa Collegiata with its frescoes by Domenico Ghirlandaio. Here's a sample: Domenico Ghirlandaio: The announcement of the death of Santa Fina (opens in overlay). (Source: Web Gallery of Art).
If your day's cycling is behind you, you could end your sightseeing by enjoying a glass of Vernaccia, and the view, from the terrace of the Museo del Vino Vernaccia (Vernaccia Wine Museum). They do wine-tastings as well. For a short article (in English) about the museum see winetrailtraveler.com
Places to stay
Find and book places to stay with Booking.com
Booking.com pages for places on this section of the route:
About these links
If you use these links to book accommodation Booking.com will pay me a small part of their commission. This helps support the costs of producing this site.
I use Booking.com to find and book places to stay when there are no campsites in the area. The large majority of hotels and many hostels are now on ‘Booking’. I like it because it means that I can get almost-instant confirmation. The rating system is also a reliable guide to the quality of the accommodation.
I’ve never had a problem finding places to keep my bike —even if it’s a cupboard or store room. I always use the ‘special requests’ field on the booking form to tell the hotel that I’m travelling with a bike, which gives them the opportunity to let me know if there’s a problem.
Many properties offer free cancellation but it’s a good idea to check the conditions as these vary from property to property.
The website bici.terresiena.it has a useful database of hotels in the Siena area and other accommodation such as agriturismi and B&Bs. The places listed in the site offer additional facilities such as secure bike storage and tools.
There's a hostel/guest house near to Certaldo: the Fattoria Basseto, they offer private rooms as well a dorm beds. There's no hostel in San Gimignano itself.
There's an excellent campsite just outside San Gimignano (the Boschetto di Piemme). A bungalow at the site might also be a good option if you are looking for budget accommodation. There's a bus service to the town (although you could also walk it pretty easily) - so you can visit without having to worry about your stuff.
Transport and services
The nearest train station to San Gimignano is at Poggibonsi, with services to Siena and to Empoli
The main tourism website for the area is the terresiena.it site (it/en) which has a section dedicated to the Chianti. For general tourist information about San Gimignano, including accommodation listings there's sangimignano.com (it/en).
Check bestsmalltownsitaly.com (en) for information about what there is to see in Certaldo and Barberino Val d'Elsa. Both towns have been awarded a Bandiera Arancione by the Touring Club Italiano. The flags are awarded to small inland towns that have "an historical, cultural and environmental heritage of merit and are distinguished for an offering of excellence, but also for offering tourists a quality welcome".