There are plenty of tour companies offering both guided and self guided walking tours of the Chianti area of Tuscany, but its not hard to cobble together your own itinerary with the aid of a good detailed map or a book like Lonely Planet’s Walking In Italy, or James Lasdun and Pia Davis’s Walking and Eating in Tuscany and Umbria both of which feature similar walking routes in the Chianti.
We chose to do the “Chianti Excursion” from Walking and Eating etc. but didn’t realize that a new edition of the book was out, and so we took along the 1997 edition. We walked from Greve in Chianti to the chapel and former villa of Parco San Michele, now a hotel/restaraunt. The route is a gradual uphill climb on a gravel road–not particularly enjoyable as it climbs to the highest point in the Chianti, although there are some nice views, particularly looking back at Greve.
From San Michele we hoofed it over to Radda in Chianti on a winding tangle of a trail (got lost just before we got to the village of Volpaia). We had lunch in this beautiful village and then continued on through the most scenic part of the route into Radda.
From Radda we opted for the San Sano destination, as opposed to going to Vagliagli. We didn’t bring much food, because we were hoping to have lunch at the recommended restaraunt, Il Poggio, just before San Polo. However, upon arrival, we were told that this restaraunt had been closed for a couple of years, and there was nothing else. Hopefully, this will be noted in the new edition of Walking and Eating. We ate the little food we had brought with us and straggled into the beautiful little village of San Sano. First stop was a tiny grocery store/trattoria, where we revived ourselves with, first, gelato ice cream and then cafe lattes. Thankfully, we had phoned ahead to make reservations at Hotel Residence San Sano, a renovated 13th century fortress, the only hotel in town and well worth the price. The meal there was also exceptional.
Thus ended our Chianti excursion. The next day we bused to Siena and then on to Montalcino to taste the famous Brunello wine first hand.