Tuscany is not a cliché — it earned it. The cypress-lined roads, the hilltop towns, the Chianti vineyards: they exist exactly as advertised, and they're still extraordinary in person. The traveler who gets it right understands that Tuscany is best experienced slowly and locally — a single agriturismo for a week rather than five towns in five days, the morning market rather than the restaurant review, the producer who opens the cave and pours you wine directly from the barrel because you asked.
What to do there
- 01
A truffle hunt in the San Miniato hills with a local trifolao and his dog — white truffle season (October–December) draws serious food buyers from across Europe, but the hunt itself is available spring and autumn for black truffles. The trifolao reads the land the way a sommelier reads a glass. Book through La Marzocca estate or local agriturismo networks. Lunch follows.
- 02
The Chianti Classico wine road (SR222) from Florence to Siena — not the tourist version, but stopping at Castello di Volpaia and Fontodi, two estates still family-owned where the winemaker pours in the cellar. Both offer tastings without reservations on weekday mornings. The Sangiovese from these estates is why Chianti has the reputation it does.
- 03
San Quirico d'Orcia to Pienza on foot — a 12km walk through the Val d'Orcia, the UNESCO landscape of rolling hills and isolated farmhouses that appears in every Tuscan photograph. Start at 7am before the day heats up. Arrive in Pienza — the world's first Renaissance planned city — for lunch at Trattoria Latte di Luna and Pecorino di Pienza from the cheese shop on Corso il Rossellino.
- 04
Cooking class at a working farm in the Crete Senesi — the silver-grey clay hills south of Siena, less visited than Chianti, where the farms are smaller and the food more grounded. A proper class starts at the market in Asciano, follows with fresh pasta, wild boar ragù, and cantuccini in the farmhouse kitchen. Full day.
- 05
Bagno Vignoni — a small thermal village in the Val d'Orcia where the piazza is a Renaissance hot spring pool. The public baths at Parco dei Mulini just below the village are free and open-air. Soak in sulphur water in a medieval mill ruin while looking over the valley. Then dinner at Osteria del Leone.
Best time to go
May for wildflowers and green hills. September and October for harvest season — vendemmia (grape harvest) and truffle season overlap and the light is extraordinary. July and August are crowded and hot. Spring and autumn are definitively the best.
Insider tip
The agriturismo model is the right way to do Tuscany. Stay at one farm for 5–7 nights, use it as a base. Prices are often comparable to a mediocre hotel in Florence, but you're eating breakfast from the estate's garden, drinking their wine at dinner, and the owner knows every road worth driving.
Book experiences
Some links earn us a small commission — at no cost to you.
Plan this trip
Where in the world
Sound of Tuscany
Make this your once-in.
Tell us how you want to feel and we'll find the right destination.
Start dreaming →