Those two rows of cypress trees on the hill south of San Quirico d’Orcia are among the most photographed in the world. You’ve seen them on postcards, on Instagram, on the cover of some paperback novel. People pull over, take the picture, and get back on the Via Cassia heading toward Montalcino or Pienza. The town itself stays quiet, unhurried, easy to miss. For a romantic road trip through Tuscany, that’s exactly the point.
San Quirico sits in the heart of the Val d’Orcia, a UNESCO World Heritage landscape of rolling hills and medieval hill towns. It’s positioned right between Montalcino and Pienza, which makes it a natural stop on any drive through southern Tuscany. But unlike its more famous neighbors, it doesn’t try to impress you. The main square, Piazza della Liberta, is understated—more of a local gathering spot than a tourist stage set. There’s a medieval catapult outside the old city gate that no longer works, and a 16th-century building that once hosted pilgrims on the Via Francigena. Nothing here is polished for a crowd. And that’s what makes it romantic in a way the bigger towns aren’t. You’re not competing for a table or a view. The pace here belongs to the people who live in it.
San Quirico d’Orcia belongs on a romantic road trip because it offers the quiet, unhurried beauty that the famous towns have lost to crowds. It’s a place to slow down, eat well, and sleep in—not to check off a list.
A Renaissance Garden and a Romanesque Church
The Horti Leonini is one of those places you stumble into and don’t want to leave. Designed in the mid-16th century by Diomede Leoni, it’s a formal Italian garden laid out on two levels, with clipped hedges, geometric flower beds, and a statue of Cosimo III de’ Medici at the center. It’s small—around 14 square metres—but it feels much bigger because of the way the light moves through it. Couples tend to linger on the benches, not saying much.
Behind the garden sits the Church of Santa Maria Assunta, a simple 11th-century structure in travertine with a wooden truss roof. The restraint of it is striking after the garden’s symmetry. A few steps away, the Collegiata dei Santi Quirico e Giulitta anchors the other end of town. Its origins go back to the 8th century, though most of what you see today is a 12th-century reconstruction in sandstone, with sculpted lions supporting the columns. The interior is mainly 17th-century. The bell tower was rebuilt around the turn of the 19th century. You can feel the layers of time in the stone.
The Landscape Beyond the Town Walls
The famous cypress trees are just a short walk or drive from the center. There are two distinct lines, each on its own hilltop, and the second one is easy to miss if you don’t know to keep going. Sunset is the moment to be there—the golden light turns the fields warm and the cypresses sharpen against the sky. It’s the kind of quiet that feels private, even if other people are standing nearby.
This is the view that stops everyone on the Via Cassia. And it’s worth stopping for—not just for the photo, but for the five minutes of stillness that comes with it.
Park a couple hundred metres back from the cypress trees and walk the last stretch. You’ll hear the quiet before you see the view, and that makes the first glimpse hit differently.
A couple of kilometres outside town, the Chapel of the Madonna di Vitaleta sits alone on a hill. It was originally built in the late Renaissance and redesigned in the late 19th century, with a single nave and a facade of Rapolano stone. The walk there through the Val d’Orcia countryside is one of the best things you can do with an afternoon. If you’re a fan of the film Gladiator, some of the surrounding landscape was used as a filming location—the grove where Maximus’s son runs to meet his father.
Note: The thermal baths at nearby Bagno Vignoni are no longer open for bathing. The setting is still worth a visit for photographs, but don’t plan on a soak.
Pici, Brunello, and a Table Under the Wisteria
You can’t talk about San Quirico without talking about pici. This hand-rolled pasta is the local staple, typically served with meat ragù, garlic sauce, or sautéed breadcrumbs. It’s simple, filling, and exactly what you want after a day in the car.
Trattoria Osena serves some of the best in town, and you can sit outside beneath a sprawling wisteria. The ravioli here is exceptional too—fresh, inventive, beautifully presented. For something more refined, Ristorante Fonte Alla Vena has held a Bib Gourmand designation in the Michelin Guide for several years running. And Hotel Il Garibaldi, which doesn’t look like much from the outside, has Friday and Saturday seafood specials that draw locals, plus a pizza menu that people swear by.
Wine here means Brunello di Montalcino, the Sangiovese that ages in the cellars of the nearby hill town. But you’ll also find good local whites from Montecarlo and the crisp Vernaccia from San Gimignano. Pair it with a plate of pecorino wrapped in fern leaves, and you’ve got a meal that asks nothing more of you than to sit and let the evening pass.
Where to Sleep Off the Tuscan Sun
San Quirico has a handful of hotels that understand what you’re looking for—a room with a view, a pool to cool off in, and a restaurant that doesn’t require leaving the property.
Hotel Palazzuolo is a boutique property with balcony views across the Val d’Orcia, an outdoor pool, and an authentic Tuscan restaurant on site. A few minutes from the main square, Boutique Villa Liberty occupies an 18th-century villa where some rooms have private hot tubs or gardens. On the higher end, Il Miraggio Relais & Spa offers five-star accommodations with a stunning spa and views that stretch for miles. Bicycle and car rentals are available at both Villa Liberty and Il Miraggio, which makes exploring the countryside easy without needing to drive everywhere.
For something that feels more like staying with a local, Palazzo del Capitano offers three different options: a luxury hotel, a medieval townhouse B&B, and a villa boutique hotel. The staff here are known for going out of their way—one traveler who arrived late after a long train ride was met with a detailed hand-drawn map and a thorough introduction to the village.
Making It Work: Timing and Logistics
Spring and autumn are the sweet spots. The weather is mild, the light is soft, and the crowds are thin. Summer brings heat and festivals, while winter offers a quiet, reflective version of the town—though some restaurants and hotels close for parts of the season.
You can see the main sights in half a day, but staying overnight changes the experience. You get the evening light, the morning stillness, and the chance to eat dinner without rushing back to the car. A single overnight is enough; two nights lets you explore the surrounding countryside at a proper pace.
A car is essential. San Quirico is rural, and there’s no regular taxi service or Uber in the Val d’Orcia. The nearest train station is Buonconvento, about 15 minutes away by car, with connections to Siena and Grosseto. A direct bus from Florence runs twice a week. But without your own wheels, you’ll miss the best parts—the drives between towns, the spontaneous stops at a farmhouse, the road that looks like it leads nowhere and turns out to be the best view of the trip. For a different pace, consider arriving by train—the slow train route through Tuscany’s rolling hills is one of the most scenic approaches to the region.
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If you’re planning a longer stay in the region, consider a guided tour of the Val d’Orcia to get your bearings on the first day. A private tour of the Val d’Orcia can introduce you to the back roads and viewpoints you wouldn’t find on your own.
Before You Plan Your Stop in San Quirico
When is the best time to visit?
March through October gives you the best weather. Spring and autumn are ideal—fewer people, comfortable temperatures, and the landscape at its most photogenic. July and August are hot, even for a hilltop town.
How long do you need?
Half a day covers the main sights, but staying overnight is the better call. You’ll want the unhurried evening and the quiet morning. Two nights lets you explore the wider Val d’Orcia at a relaxed pace.
Is San Quirico worth visiting if you only have a day in the Val d’Orcia?
Yes, especially if you’re driving the route between Montalcino and Pienza. It breaks the drive naturally and gives you a meal and a walk without fighting for parking. But if you have to choose one town to stay in overnight, San Quirico is the quieter, more romantic option.
Can you visit without a car?
Not easily. Public transport is limited—a train to Buonconvento plus a bus, or a direct bus from Florence twice a week. Taxis and ride-sharing don’t operate in the countryside. A car gives you the freedom to explore the back roads, which is really the point of being here.
The Quiet Town You Almost Drove Past
San Quirico d’Orcia doesn’t compete for your attention. It doesn’t have the blockbuster cathedral of Siena or the tower skyline of San Gimignano. What it has is a kind of stillness that feels increasingly rare in Tuscany. The kind that lets you sit in a Renaissance garden without checking your watch, or stand on a hill watching the light change over cypress trees without reaching for your phone. For a romantic road trip, that might be the most valuable thing a town can offer.
Sources and further reading
Trattoria Osena. “Trattoria Osena San Quirico d’Orcia.” 🔗
Ristorante Fonte Alla Vena. “Fonte Alla Vena.” 🔗
Hotel Il Garibaldi. “Il Garibaldi San Quirico.” 🔗
Palazzo del Capitano. “Albergo Diffuso Val d’Orcia.” 🔗
Related reading on Emily in Italy
Italy’s Best Time: Discover the Quiet Season — A guide to visiting during the quieter months, with insights on weather, crowds, and what stays open across the country.
An Italian Autumn Journey: Milan, Venice, Florence, Rome — A four-city itinerary that can easily include a detour into the Val d’Orcia, with practical advice on timing and connections.