About this tour
A 7–8 hour private tour from Siena through Val d'Orcia, a UNESCO-listed valley in southern Tuscany. You'll visit two hilltop towns—Montepulciano and Montalcino—with time to wander their Renaissance streets and medieval alleyways. The afternoon centres on a winery visit, cellar tour, and lunch pairing local Pecorino, cured meats and pasta with Brunello wine, one of Italy's most celebrated reds.
Highlights
- Cypress-lined roads and rolling Tuscan countryside
- Montepulciano: Renaissance palaces and panoramic piazzas
- Montalcino: medieval village and Brunello wine heartland
- Guided winery cellar tour with production insights
- Three-course Tuscan lunch with wine pairings
- Pecorino cheese tasting and local food traditions
- Hotel pickup and return from Siena
What to expect
Your driver collects you early morning and heads south into Val d'Orcia. The first stop is Montepulciano, where you have an hour to climb its steep streets, peek into Renaissance chapels and take in views across vineyards. After regrouping, you continue to Montalcino, another hour of wandering through narrow lanes and ancient stone walls. By midday you're at a family-run winery for a tour of their cellars and the process behind Brunello aging. Lunch follows at the winery's dining room or courtyard—handmade pasta, locally-raised meat, cheeses and seasonal vegetables, each course matched to their wines. You'll depart for Siena by late afternoon.
Good to know
Wear comfortable walking shoes; both towns involve uphill sections on uneven cobblestones. Let the operator know any dietary restrictions when booking. Infants can use a pram; infant car seats are provided. The tour runs rain or shine. Bring sunscreen and a hat for summer months.
Tour sold and operated by Viator via Viator. Descriptions on this page are original BugBitten summaries written by our team — not copied from the operator. Prices and availability are confirmed at checkout.