Siena and Surrounding Hill Towns: A Food & Wine Lover’s Guide to Tuscany

Learn about Tuscan wines with a vineyard tour and wine tasting.

From Brunello di Montalcino to Chianti to Sangiovese, the region of Tuscany has a longstanding history of producing robust, complex wines (especially red wines) with a well-deserved reputation for quality. One of the best ways to explore Tuscan culture is by visiting a local winery. Touring an enchanting hilltop vineyard such as San Giorgio a Lapi and learning about the production process, from cultivation to fermentation, is made even sweeter only by tasting the results of the process you just observed firsthand!

Visit the Palazzo Pubblico and climb the Torre del Mangia.

Purchase a combined ticket for the Torre del Mangia and the Museo Civico (Civic Museum). The 14th-century tower is quite a climb but is worth it for the panoramic views of Siena’s terracotta rooftops and surrounding Tuscan countryside. The Museo Civico, in the Palazzo Pubblico (Siena’s town hall) next door, houses several significant works of art that provide a social and cultural context for Siena’s evolution through history.

Make daytrips to neighboring hill towns.

Tuscany is full of charming, historic hilltop towns, many of which date back hundreds or even thousands of years. Often fortified by their original defensive stone walls, these are small, walkable towns that you can wander at a leisurely pace and still feel like you have done them justice in a day, or even a half-day. Most of them are not well-connected by train, but are an easy journey on Tuscany’s smooth and reasonable roads, so rent a car to take advantage of these gems in close proximity to one another. Visit Volterra for impressive Etruscan ruins, Pienza for its Renaissance-era palace and swoon-worthy views of the surrounding countryside, Montepulciano for its famous wines and charming streets, San Gimignano for its medieval atmosphere and tower houses and Montalcino for its renowned Brunello di Montalcino and picturesque views from the fortress perched at the top.

Take a cooking class to create local specialties from scratch.

Whether it’s cinghiale (wild boar native to the area), panzanella (the rustic local bread-and-tomato salad), or pici (a thick, hand-rolled pasta from Siena), much of the of magic of Tuscan food is related to the simplicity and freshness of the ingredients, which are nearly all sourced hyper-locally. To truly immerse yourself in the local culture, try crafting these dishes yourself under the guidance of an Italian chef during a cooking class. Enjoying your own creations with a “pinch-me” view of the Tuscan countryside is a priceless memory.

La Taverna di San Giuseppe | Siena

Be sure to reserve this sought-after spot a couple of weeks in advance. Its feature in the Michelin guide has solidified its standing as one of the best, and therefore most popular, restaurants in Siena. Enjoy Sienese specialties in the evocative atmosphere of an ancient Etruscan house and wine cellar from the 3rd century BC.

Osteria Quattro Venti | Siena

Elevated local specialties in a warm, refined space. Don’t miss the beef carpaccio! Attentive service (especially by European standards) and a substantial list of local Tuscan wines round out this lovely dining experience. Advance reservations recommended.

Il Bargello | Siena

Check out this intimate-yet-casual wine bar and tavern right near the Piazza del Campo in the center of Siena for wine flights, charcuterie boards, and local Sienese specialties.

Osteria La Chiacchera | Siena

It doesn’t get much more charming than this osteria with candlelit outdoor tables stacked terrace-style into a steep and narrow pedestrian street. Sample as many of their wonderful, traditional Tuscan dishes as you can. I loved the truffle ravioli and beef Scaloppina al Chianti!

Caffe Fonte Gaia | Siena

While it’s an inescapable reality that nearly all of the cafes and restaurants on the Piazza del Campo can get away with being overpriced (and sometimes sub-par) simply due to their location, it’s worth paying that price at least once to immerse yourself in the unparalleled views and ambiance of Siena’s atmospheric main piazza. Caffe Fonte Gaia is my favorite of these spots, with cheerful service, great cocktails and coffee, and typical Tuscan snacks of the region. Come for an aperitivo or a coffee and enjoy people-watching on the lively Campo.

Osteria di Porta al Cassero | Montalcino

Cozy, family-run spot for authentic, down-home Tuscan specialties. The cinghiale (wild boar) stew over polenta truly warms the soul.