A Wine Lover's Weekend in Tuscany: The Perfect 48-Hour Itinerary

Two days, one extraordinary wine region. A wine weekend in Tuscany — specifically in Montepulciano and the Val d'Orcia — is one of the finest short trips in Europe for wine enthusiasts. Here's exactly how to spend it.

Friday: Arrival Evening

18:00 — Arrive in Montepulciano. Check in to your accommodation.

19:00 — Eramo Sunset Wine Tasting. Your first evening in Montepulciano should be spent with Vino Nobile in hand and the Val d'Orcia at your feet. Our Sunset Wine Tasting is the perfect introduction to the territory: five wines narrated by an AIS sommelier, chef-prepared local pairings, maximum 18 guests, panoramic private garden.

21:30 — Dinner in Montepulciano. After the tasting, you won't need a large meal — order pici al ragù and a glass of Rosso di Montepulciano at one of the local trattorias.

Saturday: The Deep Dive

9:00 — Breakfast in the town, then a walk to San Biagio (20 minutes on foot through the vineyards). The Renaissance church in golden travertine is one of Sangallo's masterpieces — and at 9am, you'll likely have it entirely to yourself.

10:30 — Cantina visit: Salcheto or Poliziano (book the day before via their website). A proper cellar visit — barrel room, production facility, vertical tasting of 3–4 vintages. 90 minutes.

12:30 — Drive to Pienza (14km). Buy pecorino di Pienza directly from the producers on Via Rossellino. Pick up bread and local wine for a picnic.

13:30 — Picnic lunch at the Val d'Orcia viewpoint between Pienza and San Quirico d'Orcia. One of the finest lunch spots in Italy, at a cost of approximately €15 per person.

15:30 — Drive to Montalcino (40km). Visit the medieval fortress (small museum inside, worth seeing). If you haven't booked a cantina visit (Poggio Antico or Ciacci Piccolomini d'Aragona are best for visitors), walk the town and buy a Brunello bottle for later.

18:00 — Return to Montepulciano for the golden hour from the town walls.

20:00 — Chef's Secret Table at Eramo. The highlight of the weekend: seven courses, no written menu, full wine pairing, maximum 8 guests. The most refined dining experience in Montepulciano.

Sunday: The Grand Vertical

10:00 — Late breakfast. Recover from last night's menu.

11:30 — Grand Vertical Tasting at Eramo. If you've booked it: our premium vertical tasting with a Master Sommelier covers Brunello, Vino Nobile and Barolo across multiple vintages. The most educational and extraordinary wine experience in the region. €250 per person, maximum 10 guests.

14:00 — Lunch at a Montepulciano enoteca — the Enoteca Consortile on Via di Gracciano has an exceptional by-the-glass selection. Compare what you've tasted over the weekend.

15:30 — Final walk through the town. Buy two bottles to take home: a Vino Nobile Riserva (to drink in 3–5 years) and a Rosso di Montepulciano (to drink this week, with pasta).

17:00 — Departure.

A wine weekend in Tuscany, done at this depth, creates the kind of wine knowledge and sensory memory that stays with you for years.