Alentejo, Historical Pousadas & Charming Hotels

Upon your arrival in Lisbon, you’ll pick up your car rental at the airport and cross the 25 de Abril Bridge over the scenic Tagus River. You’ll then head south towards Sesimbra and pause to explore this beautiful fishing town, perhaps indulging in some fresh seafood at a local restaurant. You’ll continue to Arrábida Natural Park and take in the stunning views of the coastline from various viewpoints. Consider visiting Portinho da Arrábida, a beautiful beach with crystal-clear waters. Next, you’ll head to Azeitão, a municipality known for its wine production. You’ll have the chance to visit one of the local wineries for a wine-tasting session and enjoy some regional cheeses.

From there, you’ll drive to the historic Palmela Castle, which offers magnificent views of the surrounding landscapes and the Setúbal Peninsula.

(Approximately 60  km)

After breakfast, you’ll travel south through the Alentejo region, where you can admore in sweeping views of vast plains, wheat fields, cork trees, vineyards and olive groves. You’ll then arrive in Beja and explore the town's historical attractions, such as the medieval Castle of Beja, the Regional Museum and the Cathedral of St. James the Great. While in Beja, take some time to stroll through the old town streets and sample some local cuisine at nearby restaurants.

(Approximately 150 km)

After breakfast, you’ll leave your pousada and travel northeast for an enriching journey through historical sites and scenic landscapes. Visit the charming medieval walled village of Monsaraz, with its narrow streets, whitewashed houses and incredible views of the Alqueva Dam, the largest artificial lake in Europe. You’ll have the chance to explore the Monsaraz Castle ruins, which offer panoramic views of the surrounding countryside. You’ll then continue to Vila Viçosa and visit the Palace of the Dukes of Braganza and its Ducal Palace, a magnificent building filled with royal history and impressive architecture.

(Approximately 130 km)

After breakfast, you’ll travel to Elvas, a former episcopal city and frontier fortress of Eastern Portugal, not far from the Spanish border. You can admire the impressive 16th-century Amoreira Aqueduct, a UNESCO World Heritage Site, and explore the well-preserved Elvas Castle and its fortified walls for insight into Portugal's military history.

You’ll continue to Castelo de Vide and visit its medieval castle with panoramic views over the town and surrounding landscape. You can then wander through the narrow streets of its historic Jewish Quarter, known for its white houses and picturesque alleys.

You’ll then proceed to Marvão and visit its medieval walled village known for its cobbled streets. You can take the opportunity to walk along the well-preserved walls of Marvão Castle, perched on a granite crag which offers breathtaking panoramic views of the surrounding valleys and neighbouring Spain.

(Approximately 100 km)

After breakfast, you’ll leave your pousada and travel to Estremoz, famous for its original ceramic handicrafts and its historic castle, which also houses a pousada and offers a glimpse into Portugal’s royal past. You can explore a marble quarry or visit a marble workshop to learn about the region's marble industry, a significant part of Estremoz's heritage. You’ll then proceed to Arraiolos town, known for its handmade tapestry, and spend an overnight in Evora.

(Approximately 130 km)

After breakfast, it’s onwards to charming Lisbon, where you will spend your last 3 nights.

Today, you’ll set off on a panoramic Hop-On Hop-Off bus with a choice of three lines from Marquês de Pombal and learn about Lisbon’s history through attractions like the Belém Tower, the Monument of the Discoveries, the Jerónimos Monastery, São Jorge Castle, viewpoints of Portas do Sol viewpoint, São Pedro de Alcântara and more. You’ll even glimpse the place where Expo ‘98 was held, as well as the Lisbon Oceanarium.

You’ll then drive to the charming village of Sintra, a UNESCO World Heritage Site that once enchanted kings and inspired poets, where you’ll see the majestic and romantic Pena Palace, an astonishing fairytale castle located in one of the highest peaks in the Sintra mountain range. While in Sintra, you can also wander its narrow streets, appreciate the several handicraft shops and stop at a tearoom to taste delicious local sweet pastries like queijadas or travesseiros.

You’ll continue to Cabo da Roca, the most western point in Europe, where you’ll enjoy the sweeping vistas of the Atlantic Ocean. You’ll return to Lisbon, passing the towns of Cascais and Estoril.

(Approximately 140 km)

After breakfast, return your car rental at Lisbon airport location, before boarding your flight home to Canada.