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.

July 27, 2025

5 Best Wineries in Val d’Orcia

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.

July 24, 2025

Hi, we’re Gary and Sally 

“Our European ski story began in the 1980s and has continued with annual trips for the past 25 years. With deep experience across countless alpine resorts, skiing has become more than a sport—it’s our passion and a life that inspires our travels, adventures, and the stories we love to share.”