Howdy, I'd love some help trying to find some hiking near Castellina in Chianti. I've googled and googled, but I can't find much other than the Via Francigena which doesn't interest us too much. We are a small group of women from Colorado in our 40s and 50s traveling to celebrate my friend's retirement from teaching. We will have a car, can hike for miles, and don't need much other than lovely scenery and no crowds. An added bonus would be to make a pit stop at a family run vineyard for wine or farm for lunch. We will be in Catellina in Chianti for six nights and are staying at an AirBnB. Thanks in advance!
Is the accommodation set in stone? If you search on "best day hikes in tuscany" you get a lot of information, but good hiking might not be too near Castellina, as you're discovering.

Agree that while there are walks in Chianti - and a local tourist office should be able to help - it probably isn't the best hiking area. Further south, beyond Siena there are well known walks in the Val d'Orcia and around Monte Amiata, while north of Lucca there are mountains walks in the Massa Carrara. Try googling www.chianti.com for more tourist info

Thank you, yes, accommodations are set. I have a friend who lives in Siena, and she recommended Castellina in Chianti as it has less tourists. We do have a car, so driving a bit to reach a trailhead is no problem. Any specific recs from you? Thanks!

I stayed in Castellina in Chianti a few years back and did one fantastic hike amongst vineyards. It started south of Castellina, from Croce Fiorentina, mostly along "white roads" to the east then to the north to join Radda in Chianti (not far from 20 km in all). I got the bus back. For the rest of my stay I found that it was quite difficult to stay on a footpath as opposed to being brought back to a main road. This was before the days of GPS on the phone so I imagine it would be easier nowadays but, at my hotel, they admitted that the region was not geared up for hikers.

This is perfect, thank you! We can do this at least one day, and explore other options by car the other days. Are there any recs for small family owned vineyards nearby? Or any other recs at all? I tend to stay away from guide books recs to avoid crowds, so any tips would be helpful!
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