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.
Few places on Earth capture the timeless romance of Tuscany quite like Val d’Orcia. A UNESCO World Heritage Site, this sweeping valley of golden hills, cypress-lined lanes, and storybook villages is also home to some of Italy’s most celebrated wineries.
Framed by medieval towns such as Montalcino, Pienza, and San Quirico d’Orcia, the region’s unique terroir and centuries-old winemaking traditions have produced wines that are not only rich in character but deeply connected to the landscape.
Tuscany is known the world over for its rolling hills, cypress-lined roads, and historic towns—but it’s the wine that often leaves the most lasting impression.
From bold reds aged in ancient cellars to crisp whites enjoyed on sun-drenched terraces, Tuscany offers a wine experience like no other.
8 STUNNING TOWNS TO VISIT IN TUSCANY (2025 GUIDE) Tuscany Beyond the Postcards While many travelers rush through its cities, it’s the smaller towns that
Lucca the hidden gem of Tuscany “We Love you, “Renaissance walls completely encircle this perfectly preserved medieval city, creating ideal cycling and walking paths with panoramic countryside views. Famous tree-topped Guinigi Tower, the unique oval Piazza dell’Anfiteatro built on Roman amphitheater ruins, and charming cobblestone streets offer intimate Tuscan charm without overwhelming crowds.
Montepulciano in Italy is a popular tourist destination in Tuscany and a true paradise for connoisseurs and wine lovers. This medieval town offers exceptionally charming scenery and is beautiful on a hill in the Val d’Orcia region, surrounded by green vineyards and olive groves. Walking through the old town you will be amazed by the abundance of historic buildings, impressive churches and picturesque squares. A real highlight is that Vino Nobile di Montepulciano and Rosso di Montepulciano are two amazing red wines that are famous worldwide and can be tasted locally.
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Please email us with any questions to Gary and Sally at timelesswanders@gmail.com