Tuscany: The Italy of Every Imagination

The road from Florence to Siena through the Chianti wine country — the Chiantigiana, SS222 — is one of the most beautiful drives in the world. I have made it in a rental car in May, when the hillsides were covered in poppies and the cypress avenues leading to private villas glowed in the evening light, and I have made it again in October, when the vineyards had turned red and gold and the harvest was underway and the air smelled of fermenting grapes through the open windows. Both times I pulled over repeatedly just to stand on the road and look at a landscape so perfectly composed it seems designed rather than grown.

Tuscany is the Italy of every imagination — rolling hills, medieval hill towns, cypress trees, vineyards, olive groves, Renaissance architecture, and a cuisine that uses the landscape as its pantry. The region that produced Dante, Boccaccio, Leonardo da Vinci, and Michelangelo has been painting itself as civilization’s ideal for centuries, and it is not wrong. Tuscany is genuinely, extravagantly beautiful, and after multiple visits I have still not found the saturation point.

I base myself in different parts of the region depending on what I am looking for. Florence for art and urban energy. Siena for medieval urban fabric and the Palio fever that lingers all year. The Val d’Orcia for landscape that looks like a Renaissance painting because Renaissance painters came here to paint it. Lucca for a perfectly preserved walled city that most visitors overlook in favor of the more famous names. Each time I come back I discover something I missed — a hilltop village with a single excellent restaurant, a winery doing extraordinary things with Sangiovese, a thermal spring in the southern Maremma where you can soak for free overlooking the sea.

The key to Tuscany is not rushing between the famous cities. It is choosing a villa or agriturismo in the countryside, using it as a base, and making the day trips with time to stop for espresso in a village piazza, buy pecorino from the woman at the roadside stall, and arrive at a vineyard in the late afternoon to drink the new vintage as the sun goes down. Visit our Italy travel guide for detailed itineraries.

Why Tuscany rewards the traveler who slows down

Tuscany is not a single city or a single landscape — it is a region the size of Switzerland with astonishing internal diversity. The Chianti wine country between Florence and Siena is one face: steep hills, dense forest, and ancient villages producing Chianti Classico from the same Sangiovese vines that Medici merchants traded across Europe in the 15th century. The Val d’Orcia, south of Siena, is another: a UNESCO World Heritage landscape of soft clay hills (crete senesi), isolated farmhouses (poderi), and hilltop towns — Pienza, Montalcino, Montepulciano — that seem designed by a perfectionist set decorator. The Maremma, along the Tyrrhenian coast, is a third: wilder, less visited, with thermal springs, Etruscan ruins, and a cowboy culture (the butteri) that is genuinely foreign to most perceptions of Tuscany.

Siena is the city that permanently shifted my understanding of Italian urban beauty away from Florence. The Campo — the central piazza, shaped like a shell, the site of the twice-annual Palio horse race — is the finest medieval square in Europe. The Cathedral is as extraordinary as Florence’s and sees a fraction of the crowds. The cinta senese countryside around the city produces a distinctive, intensely flavored pork (Cinta Senese breed, identifiable by the white band around its shoulders) that is the foundation of the region’s charcuterie tradition.

The white truffles of San Miniato al Tedesco, harvested in November, attract buyers from across Europe. The thermal springs of Bagno Vignoni, built by the Romans and used by the Medici, are accessible for free soaking below the village. Tuscany keeps revealing new layers the longer you stay.

What should you do in Tuscany?

Siena and the Campo — Spend at least two full days in Siena. The Campo at evening aperitivo time is one of the great urban experiences in Italy. The Cathedral interior contains Pinturicchio’s extraordinary Piccolomini Library and Pisano’s marble pulpit — both equal to anything in Florence at a tenth of the visitors. Entry EUR 15 for the Cathedral complex.

Chianti Classico wine country — Drive the Chiantigiana (SS222) and stop at Greve in Chianti, Radda in Chianti, and Gaiole in Chianti. Winery visits: Badia a Coltibuono (tours from EUR 25), Castello di Ama (EUR 30), and Castello di Brolio (the historic home of Chianti, tours from EUR 15). Book ahead in harvest season (September-October).

Pienza and the Val d’Orcia — Pienza is a Renaissance ideal town built by Pope Pius II and the most perfectly preserved 15th-century planned town in Europe. The main street takes 10 minutes to walk and contains 15 shops selling local Pecorino cheese. Buy the stagionato (aged), wrapped in walnut leaves. The view south from the Cathedral over the Val d’Orcia is extraordinary.

Montalcino and Brunello — The hilltop town producing Italy’s most prestigious red wine. Visit the enoteca in the medieval Fortezza Medicea (wine tasting from EUR 5). The view from the fortress over the Val d’Orcia is worth the drive alone.

Montepulciano — Another hilltop wine town, producing Vino Nobile di Montepulciano. The Cantina de’ Ricci is built inside a medieval well shaft — wine tasting in what feels like a dungeon, in the best possible way. Tasting EUR 10-15.

San Gimignano — The skyline of 14 surviving medieval towers is extraordinary. Go before 09:00 to have the streets to yourself. The Vernaccia di San Gimignano white wine tasted at a local cantina is the perfect aperitivo. Day trip from Florence or Siena, 1.5 hours each way.

Terme di Saturnia — Free thermal hot springs in the southern Maremma, a natural cascade where the water temperature stays at 37.5C year-round. One of Italy’s genuine hidden treasures. Go on a weekday morning for minimum crowds. Three hours south of Florence by car.

Where should you eat in Tuscany?

• Osteria di Passignano — Badia a Passignano, Chianti. Michelin-starred restaurant inside a 10th-century abbey, surrounded by Antinori vineyards. Pici al ragu di cinghiale (wild boar pasta), bistecca from Cinta Senese. EUR 60-90 per person. Book ahead.
• Trattoria Cammillo — Via del Porrione, Siena. The most genuine cucina senese in the city. Pici all’aglione, ribollita, grilled Cinta Senese. Dinner EUR 25-40 per person.
• Il Leccio — Sant’Angelo in Colle, near Montalcino. Village trattoria with perhaps the finest pici in the region and honest Brunello pours. EUR 20-35 per person.
• Dario Cecchini’s Macelleria — Panzano in Chianti. The most famous butcher in Italy. Free tastings of cured meats at the shop. Book for dinner at Solociccia (EUR 50 set menu) for the full experience of what one man has done for the craft of butchery.
• La Solita Zuppa — Via Porsenna 21, Chiusi. A small restaurant that serves nothing but soups — legume soups, bread soups, acquacotta — in a setting of extreme simplicity. EUR 15-25. Reservations essential.
• Il Pozzo — San Quirico d’Orcia. Simple, reliable, spectacular views over the Val d’Orcia. Pasta al pomodoro and grilled lamb are both excellent. EUR 25-40 per person.
• Enoteca Italiana — Fortezza Medicea, Siena. A wine bar inside the Medici fortress with over 1,500 labels at cellar prices. Order a glass of Brunello, sit on the ramparts, and watch the Val d’Orcia light change. EUR 5-15 per glass.

Where should you stay in Tuscany?

Budget (EUR 50-110/night) — Agriturismo stays in the countryside can be found from EUR 60 with breakfast. Siena has several family-run B&Bs from EUR 70-90. Il Giardino in Siena (doubles from EUR 75) is well located and consistently good value.

Mid-Range (EUR 120-250/night) — Agriturismo Poggio Conti in Greve (doubles from EUR 130) is a working Chianti estate with a pool and exceptional wine. La Locanda del Loggiato in Bagno Vignoni (doubles from EUR 120) is a beautifully restored medieval inn with thermal pool access.

Luxury (EUR 280+/night) — Castello di Casole (from EUR 500) is a 10th-century castle in the Sienese countryside with its own vineyards and spa. Borgo Santo Pietro (from EUR 450) is an extraordinary 13th-century hamlet near Siena with organic gardens and a Michelin-starred restaurant.

When is the best time to visit Tuscany?

May-June is the peak of Tuscan beauty — wildflowers, lemon blossoms, mild temperatures, and the landscape at its most vivid green. September-October is harvest season — grapes, olives, truffles — and the landscape turns amber and gold. October is particularly fine and slightly less crowded than September.

July and August are hot (35-38C) but the hill towns are cooler than coastal areas. The Palio in Siena runs July 2 and August 16 — the city is extraordinary but accommodation books out months ahead. November through March is the slow season with the lowest prices and the most atmospheric winter light.

Allow at least a week to do Tuscany justice. See our Italy travel guide for detailed itineraries combining Tuscany with Rome, the Amalfi Coast, and Cinque Terre. Browse all Italian destinations.