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From San Gimignano, it was incredibly easy to take one day to road trip through the region of Chianti. It was easily one of the best days while in Tuscany, as the hilltop towns of Chianti are quieter, off-the-beaten path, and incredibly picturesque. The landscapes in Chianti are drastic, raging from thick green forests, to historic towns, and rolling vineyards and olive orchards. One day was plenty of time to hop through the towns, stop for a long lunch, and enjoy the scenery.

Using Google Maps, it’s easy to plug in the directions to get from one town to the next. If all else fails, just follow the road signs for the direction of the town you want to get to.

Here’s how we spent one day in Chianti.


We started the day in San Gimignano, leaving town at around 9:00 am. It’s about an hour and half drive into the first town.

To note: Most of the towns are meant for walking around, enjoying the view, so we often popped into one and if we felt like we saw it, we moved on to the next!

First stop: Castellina in Chianti

+ Took a quick stop to walk the small streets and checkout the town.

Second stop: Radda in Chianti

+ Grabbed a tasty focaccia with prosciutto and pecorino at the Casa Porciatti dal 1965. It’s a lovely shop where you can pickup snacks and drinks for the road.
+ Took in the panoramic views from the walls of the city, it was truly stunning.

Third stop: Gaiole in Chianti

+ This small town could or could not be skipped, there was not a whole lot going on.
+ We did find a beautiful winery at the top of the hill nearby inside an old castle called Castello di Meleto, that was beautiful spot to grab a glass of wine.

+ Lunch: As we made our way to Panzano, we stopped at this small town that was slammed with cars. We couldn’t figure out where all these people were going, then we saw everyone at this restaurant. Listed on the Michelin Guide, Osteria Le Panzanelle was a phenomenal meal and we spent two hours on the terrace eating delicious homemade pasta.

Fourth stop: Panzano in Chianti

+ This was on our list as we know Anthony Bourdain stopped at the famous world’s best butcher Officina della Bistecca. It is worth stopping for a taste!
+ At the top of the hill lies a picturesque church with panoramic views.

Fifth and final stop: Montefioralle

+ This was easily our favorite stop as the town was empty and incredibly picturesque.
+ There is not much here, just incredibly quaint and lovely winding roads.

Other possible stops you could add:

Greve in Chianti
La Panca
Lecchi in Chianti

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