With a castle or keep on every hill (many dating from the year 1,000 or thereabouts) and slopes cloaked in evergreen oak, vineyards and olive groves, the landscape of the Chianti Hills is breathtaking. It is not hard to imagine why families from Florence and Siena battled over this beautiful land for centuries (Napoleon passed through as well). Based in Gaiole (at our own castle), what drew us to town in October was L'eroica, an annual bike ride, originally put on to promote the traditional white gravel roads of Tuscany and today attracting a throng of mostly Italian riders, by design on vintage bikes (your bike must be pre-1987) and many riders outfitted in wool. Rest stops featured fagiole, not power bars, and the mood is festive. We opted for the 75 km route, not the full 205 kilometers, returning to town in the mid afternoon. It's the best single day I've ever spent on a bike. Though the exact course changes from year to year (riders can choose from four different routes), one ride has permanent signposts for those who want to cycle outside of the official event. The Italian Alpine Club maintains a series of trails through the oak- and pine-clad woods and, though we managed to get terribly lost on a hike from Gaiole, we did make it to Badia a Coltibuono in time for a memorable lunch. We can also recommend the castle, food and wine at Brolio, which has been in the Ricasoli family since 1141
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53013 Gaiole in Chianti, Province of Siena, Italy