Travel south to Porto, where the city’s historic center, a UNESCO World Heritage Site, showcases its rich trading past and offers insight into the wine culture that colored its history. A visit to the Stock Exchange Palace and a boat tour along the Douro River provide glimpses into the city’s commercial and aesthetic significance through the ages.

Next, journey to Coimbra, home to one of the oldest universities in Europe. The university’s historic buildings and the Joanina Library stand as monuments to Portugal’s scholarly and artistic achievements. Nearby, the Roman ruins of Conímbriga reveal intricate mosaics and a glimpse into ancient life on the Iberian Peninsula.

In Lisbon, delve into the city’s multifaceted history, from its Moorish legacy to the monumental Jerónimos Monastery, which commemorates Portugal’s golden age of exploration. A day trip to the fortified town of Óbidos offers a step back into medieval times, with its cobbled streets and ancient walls offering a picturesque journey through history.

In the Alentejo region, visit Évora, another UNESCO World Heritage site famed for its well-preserved Roman Temple and the haunting Chapel of Bones. The city’s history as a center of learning and religion during the Renaissance is palpable in its labyrinthine streets and grandiose architecture.

Finally, conclude in the Algarve, where maritime history takes center stage. Explore the old town of Faro, with its medieval walls and Gothic cathedral, and visit Sagres to stand at the southwesternmost point of continental Europe, where Prince Henry the Navigator once sponsored early voyages of discovery.