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 5 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.
Read This Next

Introducing
FX Excursions
FX Excursions offers the chance for once-in-a-lifetime experiences in destinations around the world.
#globility
Insta FeedDaily
Feb 13, 2025Trendy Delano Miami Beach Hotel Reopens This Year
Ennismore and partner Cain International are expecting to reopen the well-known Delano Miami Beach hotel in 2025 after completing a full renovation.
Sponsored Content
Sailing the Ionian Sea: Explore Greece’s Nautical Gems
Sailing the Ionian Sea is an enchanting way to experience Greece's breathtaking islands and pristine waters. Known for its favorable winds, calm seas and stunning landscapes, the Ionian Sea offers a paradise for both experienced sailors and those looking to explore for the first time. From lively beaches to secluded bays, these waters have something for every traveler seeking adventure and relaxation.
Daily
Feb 13, 2025Florida’s Amrit Ocean Resort Launches Wellness Retreat Series
Situated on Florida’s Singer Island, recently opened Amrit Ocean Resort launches a wellness retreat series. Held monthly, this series aims to inspire longevity. The first retreat kicks off Feb. 27.
Daily
Feb 13, 2025Aman to Open Its First Property in Bangkok
More than 35 years after opening its first property, Amanpuri, in Phuket, Aman returns to Thailand with the opening of Aman Nai Lert in Bangkok. Set to debut April 2, the 52-suite property lies within privately owned Nai Lert Park, offering guests a secluded haven in the middle of the bustling city, much like sister property Aman New York.
Sponsored Content
A Summer Sojourn Along Europe’s Rivers with AmaWaterways
This summer, elevate your vacation experience with award-winning AmaWaterways. Offering a seamless blend of unparalleled luxury, authentic cultural experiences and unrivaled service, AmaWaterways cruises are the perfect way to uncover the heart of Europe during the sunniest season with itineraries that glide along the continent’s most iconic rivers, including the Danube, the Rhine, the Seine and the Douro.
Daily
Feb 12, 2025Colorado Dragon Boat Film Festival Returns in March
Celebrating the best of Asian and Asian American filmmaking, Colorado’s Dragon Boat Film Festival is a fun mix of screenings by established and emerging artists. The theme of this year’s event is Honoring Our Past to Guide Our Future, held March 14–16 at Denver Sie Center.
6 Destinations and Hotels for Solo Women Travelers
Daily
Feb 12, 2025New SIRO Hotel to Open in Tokyo in 2029
eFlyer News
Feb 12, 2025eFlyer Deals
Feb 12, 2025Have a Galentine’s to Remember at Holston House Nashville
Available for stays Feb. 13–17, Holston House Nashville’s Galentine’s offer is sure to elevate your girls’ trip to the next level. This offer starts at just $50 above the hotel’s standard room rate and comes with:
Sponsored Content
A Word with Nat Pieper, oneworld CEO
Name: Nat Pieper Title: CEO at oneworld City: Dallas, Texas First job: Stadium vendor
eFlyer Deals
Feb 12, 2025Last-Minute Valentine’s Day Deal at The Benjamin Royal Sonesta Hotel
Still looking for a Valentine’s Day offer? The Benjamin Royal Sonesta Hotel, in New York City, has the LOVE Ben promotion available. With this offer, enjoy a stay in the hotel’s signature suite, as well as a private, late-night MoMA tour for two (with transportation included).
ShareThis