If you’re dreaming of rolling hills, vineyard views, and sipping wine straight from the source, Tuscany should be at the top of your list. This region is overflowing with charming towns that are perfect for a relaxed, wine-focused getaway. From famous Chianti stops to lesser-known gems, here are the best towns in Tuscany where the wine is flowing and the scenery is unforgettable.
Montalcino
Famous for its bold Brunello wines, Montalcino is perched high on a hill with sweeping views of the Val d’Orcia. The town is peaceful, walkable, and packed with tasting rooms and wine estates nearby. It’s a must-visit for serious red wine fans.
Montepulciano
This Renaissance-era town is known for Vino Nobile di Montepulciano, a smooth red wine you can sample right in the historic center. Its cobbled streets lead to panoramic overlooks and centuries-old wine cellars. You’ll find just the right mix of beauty, history, and bold flavor here.
Greve in Chianti
Often considered the heart of the Chianti wine region, Greve is a great base for exploring Tuscany’s most iconic wine area. The town has a lively central square, weekend markets, and easy access to countless vineyards. It’s the perfect place to start your Chianti Classico adventure.
Pienza
Small but spectacular, Pienza is more famous for its pecorino cheese — but don’t let that fool you, the wine scene here is strong. The surrounding countryside is dotted with boutique wineries and postcard-worthy views. Pair the wine with local cheese for the ultimate tasting experience.
San Gimignano
Known for its medieval towers, San Gimignano also produces Tuscany’s most famous white wine, Vernaccia di San Gimignano. The town itself is a stunner, and the surrounding hills are lined with vineyards open for tastings. It’s one of the few places in Tuscany where white wine steals the spotlight.
Radda in Chianti
This tiny hilltop town offers a quieter, more intimate Chianti experience with views for days. Its winding streets and ancient walls are full of charm, and the nearby wineries are easy to reach. It’s ideal if you want to sip Chianti in a relaxed, less touristy setting.
Cortona
Cortona is an artsy town with a growing wine scene, set high above the valley with panoramic views in every direction. Made famous by Under the Tuscan Sun, it has all the beauty you’d expect, plus some excellent local reds from nearby vineyards. It’s a great blend of wine, culture, and scenery.
Bolgheri
On the Tuscan coast, Bolgheri is a different kind of wine country — this is where Tuscany’s Super Tuscans were born. Drive the famous cypress-lined road into town, then settle in for tastings of world-class reds. It’s off the usual tourist trail but completely worth the detour.
Castellina in Chianti
This charming town in the Chianti hills combines history, wine, and gorgeous views in equal measure. Wander its old streets, explore the tunnels beneath the town, and stop in for tastings at nearby estates. It’s a lovely stop for anyone looking to slow down and sip.
Lucignano
Tucked between Siena and Arezzo, Lucignano is less visited but packed with Tuscan character. The town’s circular layout and medieval streets are fun to explore, and local wineries serve up classic Tuscan reds with zero crowds. It’s a great pick if you want authenticity and scenery without the buzz.
Laura Lynch, creator and writer of Savored Journeys, is an avid world traveler, certified wine expert, and international food specialist. She has written about travel and food for over 20 years and has visited over 75 countries. Her work has been published in numerous guidebooks, websites, and magazines.