Perched On A Hill Is This Medieval UNESCO Site With Some Of Italy's Best Food, Wine, And Views

You may know Tuscany as the central Italian destination where Rick Steves ate the best meal of his life. You probably also keep the region in mind for sumptuous hotels and spas like the Monteverdi Tuscany. But in the Tuscan province of Siena — located less than two hours from Florence  and one hour southeast of the city of Siena — you'll also find the Val d'Orcia. A hilly medieval UNESCO site that's equally esteemed for its food and wine cultures as it is for its views that all but assure excellent photos.

Although you might not know it, you've almost certainly seen photos of it before. Simply imagine a winding road bordered by pointy cypress trees — one of Tuscany's most iconic sights — and you're probably picturing the groves in the tiny town of San Quirico d'Orcia.

However, the memorable arbors aren't all that have made the Val d'Orcia a UNESCO World Heritage site since 2004. First, there's its history, which stretches back to even before the Etruscan period. Per UNESCO, its inimitable landscape of farmland was in evidence by the 13th or 14th century, when it was first captured by the artists of the Sienese school. As such, a trip to the Val d'Orcia is a step back into Italy's history — with views that remain practically unchanged.

Staying in an agriturismo, or a lodging that's also a working farm, isn't just the best way to soak in a slower lifestyle in the Val d'Orcia  — it's also among the cheapest types of lodgings you'll find in the area. The town of Pienza, for example, which became a UNESCO World Heritage Site in 1996, is a living, breathing Renaissance site centered around a cute piazza. But just outside its limits, there's an impressive collection of farmstays for around $100 a night.

Though more expensive than the lodgings listed on dedicated farmstay websites like Agroturismo, it's also worth checking in at one of the apartments at La Fonte. There, a farm-fresh breakfast buffet is included daily, and the restaurant also features game such as rabbit and boar alongside pasta in cream sauce prepared with local truffles.

If you're hoping for a night away from your agriturismo, but with the same ethics, it's likely that your hosts will point you in the direction of Podere Il Casale. Located on an organic farm, you'll find fresh homemade pasta, as well as meats and cheeses from animals raised on-site. And, for around $70, the four-course menu can include dishes like roasted goat with sour butter cabbage, followed by sheep's milk pudding with salted caramel.

Once you've tired of Pienza and its famed cheese, flowers and unique landscapes, it's time to venture out of town for a tipple. What types of wines should you look for in the Val d'Orcia? Brunello di Montalcino and Vino Nobile di Montepulciano — both reds produced from Sangiovese grapes — are a good option. Prefer whites? Look for the less common, but no less taste bud-tickling Orcia Bianco, made mostly from Trebbiano grapes.

For one of the more budget-friendly ways to enjoy your wine and the gorgeous landscape that grows it, head to Tiberini Winery, located in the hills of Montepulciano. There, for around $47, you'll be treated to a two-hour light lunch that includes four tastings, plus bread with local salumi and cheeses to help soak it up.

Alternatively, you can also make Montalcino your destination. Home of Brunello — as well the Enoteca la Fortezza di Montalcino, a 14th-century fortress where you can enjoy it — tastings are just $30 and include meats, cheese made in Pienza, bread, and three samplings. Outside the fortress, at Sasso di Sole, you can meet the Terzuoli family for a tour of the cellar where the wines are made and stored, fleshed out by three sips and the usual snacks. If the best way to get to know a region is through its food, drink and views, you'll leave as an expert in all that Val d'Orcia has to offer.