Morning: Arrive in Lisbon and take a direct train to Montemor-o‑Velho. Check‑in at the charming Casa do Rio Guesthouse, enjoy a light breakfast with fresh local pastries.
Afternoon: Explore the historic Montemor-o‑Velho Castle, strolling along its medieval walls and admiring panoramic views of the Mondego River valley. Afterwards, wander through the quaint town square and visit the Church of São João Baptista.
Evening: Savor a traditional Alentejo dinner at Restaurante O Frade, featuring migas and local wines. Return to the guesthouse for a relaxed night and early rest.
Find HotelsMorning: Join the Alentejo Walking Festival kickoff in Montemor-o‑Velho, meeting fellow hikers at the festival hub. Participate in a guided 10 km walk through the rolling olive groves and vineyards.
Afternoon: Travel by bus to Évora (≈1 hour). Check‑in at the centrally located Hotel Mãe d’Água. Begin exploring the UNESCO‑listed historic centre, starting with the impressive Roman Temple (Templo de Diana).
Evening: Attend the festival’s cultural evening in Évora’s main square, featuring live folk music and regional cuisine stalls. End the night with a leisurely stroll under the illuminated Évora Cathedral.
Find HotelsMorning: Visit the hauntingly beautiful Capela dos Ossos (Bone Chapel) and the nearby University of Évora courtyard, soaking up centuries of history.
Afternoon: Enjoy a relaxed lunch at Taberna Típica before heading back to Lisbon by train. Use any remaining time for souvenir shopping in the historic market.
Evening: Arrive in Lisbon, catch your flight or continue onward. Reflect on the Alentejo’s gentle pace and vibrant traditions.
Find HotelsTo extend your stay, consider adding a day in the Algarve for beach relaxation or a visit to the historic town of Beja. If you need to shorten the trip, skip the evening cultural program in Évora and replace the full‑day festival walk with a shorter 5 km route, which still captures the region’s scenery while freeing up time for extra sightseeing.