With its rolling vineyards, medieval villages, and winding cypress-lined country lanes, Chianti is the Tuscany dreams are made of. Bookended by Florence to the north and Siena to the south, this stretch of countryside is home to the prestigious Chianti DOC and Brunello di Montalcino wines, as well as the region’s classic rustic cuisine—making it a mecca for foodies from across the globe. Wine tasting, cooking classes, and truffle hunting adventures top the to-do list alongside hiking, biking and horseback riding excursions through the idyllic countryside.
Fall is harvest season in the Chianti hills, where olive groves produce extra-virgin oil, vineyards grow the fruit for bold Tuscan wines, and woodlands are full of wild mushrooms and truffles. The hilltowns in this region celebrate this seasonal bounty with sagre, local food festivals that highlight area specialties. Spring is also glorious in this rural corner of Tuscany; backroads and trails fill with bikers and hikers enjoying the countryside’s bright green hills and colorful flowers.
Chianti is famous for its picturesque hilltop villages, but it’s hard to get to these remote outposts if you’re relying on public transportation. There are very few rail lines linking the towns, and local buses run according to school and office hours, so often you can only travel in the early morning and late afternoon. The best way to explore is by renting a car (from agencies in Florence or Siena) or by bike or e-bike.
The hills in Chianti are full of natural hot springs, and locals have been soaking in their therapeutic waters since Etruscan times. Do as the Tuscans do, and unwind in the mineral-rich thermal baths at Bagni San Filippo (located outside Castiglione d’Orcia), Chianciano, or San Casciano dei Bagni. Some of these are natural hot springs that you can enjoy for free. At others, you can pay to enter a terme spa boasting pools, lounge chairs, and spa treatments like massages and mud baths.
