There are several wineries around Reguengos (part of the wine route), including the acclaimed Herdade do Esporão, 7km south of town. Under the direction of oenologist David Baverstock, it produces a wide variety of wines for domestic and overseas markets. There are tours through the extraordinary wine cellars, among the largest in Portugal.
Parts of the cellars were sourced from the same factory that supplied the underground in Lisbon. It’s worth splurging at the wine cellar shop or the restaurant. Reservations are essential for dining at the restaurant (meals around €50), and recommended for booking a tour (which are sometimes booked solid by groups; there’s typically one English-language tour each day). If you show up without a reservation, you can still enjoy wine tasting in the wine bar. Charcuterie, cheeses and other snacks are available.
The small on-site museum features the original artwork done for the wine labels of Esporão’s annual reserve collection; each year a famous Portuguese artist is given the honour. The property’s border was defined in 1267 and it has vestiges of Roman times.