5 Best Wineries to Visit in Chianti, Tuscany (2025 Guide)

Exploring Chianti through its wineries is one of the most rewarding ways to experience Tuscany. In this guide, we share five of our best wineries to visit in Chianti—each offering a unique blend of tradition, wine making, and breathtaking scenery.

You’ll find practical travel tips, detailed introductions, and honest pros and cons for each winery, along with advice on where to stay and the best times to visit.

Hi, we're Gary and Sally !

Hi, Where Gary and Sally we are the Timeless Wanderers. We retired early to travel full time. We left Australia in October 2022, to travel. After spending over 30 years in hospitality and devoting our time to our children. It was now our time, our dream was always to move to Europe when we retired, we have been coming here since the 80’s.