IN THE DAYTIME, ALENTEJO’S visitors tour a verdant countryside dotted with vineyards, cork trees and churches that look like they jumped out of a fairy tale. At night, many travelers sleep in a castle, in one of the Pousadas de Portugal where the rates don’t require a royal income.

With most visitors to Portugal heading to Lisbon, the Algarve or the Duoro wine region, the Alentejo towns remain uncrowded and serene. When I stopped by Casa Agricola José de Sousa Rosado Fernandes Winery in the town of Reguengos de Monsaraz, the “guide” had to clean his grape-stained hands from moving hoses around between tanks. Down in the deep cellar, though, he showed me huge clay vats that mimic the same fermentation process used in ancient times. That night we ordered a bottle from the winery at a restaurant two blocks away.

The Alentejo region has about 30 percent of Portugal’s land mass but only 7 percent of its population. Meal times are often farm-to-table without much effort or distance. A glass of wine inside the Estremoz or Monsaraz fortresses can be accompanied with aged cheese, cured olives, fresh bread and olive oil from lands just outside the centuries-old walls.

The main city, Évora, has fewer than 60,000 residents and is still partially enclosed by a medieval wall. This compact town, a UNESCO World Heritage city, features Roman temple ruins from more than 2,000 years ago, a former palace and Gothic churches. With several wine tasting rooms and stores, this makes a great place to get an overview of local wines.

Portugal boasts nine main grape varieties, but few are familiar to foreigners. For those who can’t tell an Alfrocheiro from a Roupeiro, the small blessing here is most wines are blends, anyway. With wines priced mostly for the local market, a wrong choice won’t cost much.

In the villages, locals don’t eat out much, so finding the best dining spot is often a matter of following the sound of laughter to a café. For a true local experience head to Borba, where a few cafés serve wine made with traditional methods in the same space as the café serving food. While you’ll find dozens of wineries scattered around Alentejo, many are clustered around Borba, Vila Viçosa and Estremoz — also popular stops for historic architecture created with marble mined nearby and castles straight out of an epic adventure movie.