Tuscany: Hilltop Villages, Chianti Vineyards & the Art of the Slow Journey

Tuscany is the landscape that has defined the Western world's idea of beauty since the Renaissance — rolling hills of olive groves and vineyards, cypress-lined roads ascending to fortified hilltop towns, and a quality of light in the late afternoon that transforms even an ordinary hillside into something worthy of a painting. No other region in the world rewards slow, unhurried travel more generously.

The region's genius is its layering: world-class art and architecture in Florence and Siena, extraordinary wine in the Chianti Classico and Brunello di Montalcino zones, a cuisine of remarkable depth and simplicity, and a landscape that changes character from valley to valley. A week here is never enough.

Where to Stay: The Finest Addresses

Rosewood Castiglion del Bosco (rosewoodhotels.com/en/castiglion-del-bosco) near Montalcino occupies a medieval Sienese castle estate of 4,200 acres in the Val d'Orcia — a UNESCO World Heritage landscape. The 42 suites and villas are distributed across the borgo (hamlet), with a 9-hole golf course, a working Brunello di Montalcino wine estate, and a spa built into a 12th-century tower. This is the benchmark luxury agriturismo experience. Villas from $3,000/night. The estate's own Brunello DOCG is one of the finest produced in the zone.

Adler Thermae (adler-resorts.com/thermae) in Bagno Vignoni — a thermal spa village in the Val d'Orcia whose main piazza is a Renaissance bathing pool — is the premier wellness destination in Tuscany. The thermal baths (fed by natural 126°F sulphurous springs), the vast indoor/outdoor spa complex, and the panoramic hillside setting combine for one of the most restorative hotel experiences in Europe. Rooms from $600/night.

Il Pellicano (ilpellicanohotel.com) on the Monte Argentario peninsula of the Tuscan Maremma is the most glamorous hotel in Tuscany — perched above the Tyrrhenian Sea on a private headland, with a seawater pool cut into the rocks, rooms decorated with the refined personal taste of its American founder Patricia Cicogna, and a Michelin-starred restaurant. Suites from $1,200/night.

The Chianti Classico Wine Road

The Strada del Vino Chianti Classico (stradachianti.it) runs through the heart of the zone between Florence and Siena — the 40km of hills that produce Sangiovese-based red wines at their most elegant. The Black Rooster (Gallo Nero) on a bottle of Chianti Classico is the denomination's mark of origin, established by the Consorzio del Vino Chianti Classico (chianticlassico.com).

The estates most worth visiting include Antinori nel Chianti Classico (antinori.it/en/winery/antinori-nel-chianti-classico) — a spectacular underground winery designed by Marco Casamonti, burrowed into a hillside vineyard between Bargino and Tavarnelle, open for tours and tastings. Castello di Ama (castellodiama.com) near Gaiole is as celebrated for its contemporary art collection (site-specific works by Anish Kapoor, Louise Bourgeois, and Daniel Buren, among others) as for its wines. Badia a Coltibuono (coltibuono.com) near Gaiole offers stays in a converted 11th-century Vallombrosan monastery estate, with excellent wine, olive oil, and a cooking school.

Beyond Chianti: The Val d'Orcia

South of Siena, the Val d'Orcia — inscribed as a UNESCO World Heritage Cultural Landscape in 2004 — is Tuscany at its most cinematically beautiful: the rounded clay hills (crete senesi), the isolated farmhouses (poderi), the cypress-lined tracks (strade bianche), and the medieval villages of Pienza, Montalcino, Montepulciano, and Bagno Vignoni arranged across the landscape like an open-air museum.

Pienza (comune.pienza.si.it), planned in the 1460s by Pope Pius II as an ideal Renaissance city, contains the finest concentration of 15th-century urban design in Italy within its tiny cathedral square. The Pecorino di Pienza — sheep's milk cheese aged in walnut leaves, terracotta, or oak barrels — is the local delicacy and sold at several shops around the main piazza.

Getting There

Florence Peretola Airport (FLR) and Pisa Galileo Galilei (PSA) are the main entry points. A hire car is essential for exploring the countryside — Tuscany without a car is a lesser experience. The strade bianche (white gravel roads) of the Crete Senesi are best driven in a vehicle with reasonable ground clearance, ideally in the early morning when the dust has settled and the light is golden.