Tour Overview
Lisbon & Alentejo Historic Pousadas is a 9-day, 8-night self-drive vacation combining the landscapes, fortified towns, heritage hotels and regional culture of the Alentejo with three nights in Lisbon. The journey begins at Lisbon Airport and travels south through Arrábida and the Setúbal Peninsula before continuing through Beja, Monsaraz, Vila Viçosa, Elvas, Castelo de Vide, Marvão, Estremoz, Arraiolos and Évora.
A defining feature of this Portugal self-drive itinerary is the accommodation. Most nights are spent in historic Pousadas or similar heritage hotels, including properties housed in castles, convents and other culturally significant buildings. The route combines independent driving with time to explore medieval villages, castles, wine country, traditional crafts, regional cuisine and the broad rural landscapes that distinguish the Alentejo.
After five nights traveling through the Alentejo, return to Lisbon for a three-night stay. A 48-hour Lisbon Hop-On Hop-Off sightseeing pass is included for exploring the capital, with routes serving Belém, the historic center and modern Lisbon. The supplier itinerary also suggests a self-drive excursion to Sintra, Cabo da Roca, Cascais and Estoril during the Lisbon stay.
Day-by-Day Itinerary
Day 1 - Lisbon, Arrábida & Palmela
Arrive at Lisbon Airport, collect your rental car and begin your journey south across the 25 de Abril Bridge. Continue toward Sesimbra and the Arrábida Natural Park, where coastal viewpoints, beaches and fishing communities introduce you to the landscapes south of Lisbon.
Continue to Azeitão, an area known for wine and regional food traditions, before driving to Palmela and its hilltop castle overlooking the Setúbal Peninsula. Overnight at a historic Pousada in Palmela or Alcácer do Sal.
Day 2 - Palmela or Alcácer do Sal to Beja
Travel into the Alentejo, a region characterized by broad plains, cork oak landscapes, vineyards, olive groves and historic towns. Arrive in Beja and explore its old center, castle, cathedral and regional heritage before enjoying time for local dining. Overnight at a Pousada in Beja.
Day 3 - Beja to Monsaraz & Vila Viçosa
Drive northeast to Monsaraz, a medieval walled village overlooking the Alqueva landscape. Walk through its narrow whitewashed streets and visit the castle area for panoramic countryside views.
Continue to Vila Viçosa, closely associated with Portugal’s royal history and known for its Ducal Palace and marble architecture. Overnight in Vila Viçosa or Elvas.
Day 4 - Vila Viçosa, Elvas, Castelo de Vide & Marvão
Travel to Elvas, a historic fortified city near the Spanish border, then continue north to Castelo de Vide. Explore its medieval castle, old Jewish Quarter and whitewashed streets before driving on to Marvão.
Set high on a granite ridge, Marvão is one of the Alentejo’s most dramatic fortified villages, with stone streets, medieval walls and wide views across the surrounding valleys. Overnight in Marvão or Estremoz.
Day 5 - Marvão, Estremoz, Arraiolos & Évora
Drive to Estremoz, a historic town known for its castle, marble heritage and traditional crafts. Continue to Arraiolos, famous for its handwoven rugs and long tradition of decorative textile craftsmanship.
Arrive in Évora, the Alentejo’s best-known historic city, and settle into a Pousada for the night.
Day 6 - Explore Évora & Return to Lisbon
Spend the morning discovering Évora, a UNESCO World Heritage city with a historic center shaped by Roman, medieval and later Portuguese architecture. Highlights may include the Roman Temple, Évora Cathedral and the Chapel of Bones.
Enjoy time for Alentejo cuisine and regional wines before driving back to Lisbon. Check in for a three-night stay at a Pousada or similar heritage hotel.
Days 7-8 - Lisbon Sightseeing
Use your included 48-hour Lisbon Hop-On Hop-Off sightseeing pass to explore the Portuguese capital at your own pace. The sightseeing routes serve major areas and landmarks including Belém, Jerónimos Monastery, the Monument to the Discoveries, São Jorge Castle viewpoints, central Lisbon and the modern Oriente district.
Suggested Self-Drive Excursion: Sintra, Cabo da Roca, Cascais & Estoril
The supplier itinerary also suggests using one of your Lisbon days for a self-drive excursion to Sintra, with time to explore the historic center and Pena Palace area, followed by Cabo da Roca and the Atlantic coast. Return to Lisbon via Cascais and Estoril. This is suggested sightseeing and is not listed by the supplier as a separately included guided tour.
Day 9 - Depart Lisbon
After breakfast and hotel check-out, drive to Lisbon Airport, return your rental car and continue with your onward journey.
