The westernmost country of mainland Europe, Portugal has long been a frontier for people surging in from the east—Celts, Romans, Moors—leaving their mark on its windswept landscapes. Explore this cultural melting pot with a private guide as you step back in time at hilltop castles in the Alentejo region, follow in the footsteps of Europe’s great explorers in atmospheric Lisbon, and sip on port in the historic wine estates of the Douro Valley. From Paleolithic rock engravings to Roman ruins, Moorish fortresses to evocative street murals, discover Portugal’s rich history and its emerging creative renaissance.
Arrive in Lisbon and transfer to your hotel. Spend the rest of the day exploring the Portuguese capital at your own pace.
Learn about the golden age of Portuguese exploration on a walking tour of the historic Belém district and the ornate Jerónimos Monastery. Walk among the hilltop ramparts of São Jorge Castle, a Moorish fortress that dates to the sixth century, and take in breathtaking views of Lisbon and the Tagus River. This afternoon, hop on an iconic Lisbon tram, carefully restored to its original style, for a private ride across the city’s seven hills. Rumble down narrow, decadent streets and soak up the atmosphere of Lisbon’s diverse neighborhoods, from dreamy old Alfama to elegant Chiado.
Venture west to the cosmopolitan Estoril coast, and join your private guide for a stroll through the fairytale-like old town of Sintra—where the entire landscape has been named a World Heritage site. Visit the spectacular Pena Palace, and unlock the mysteries of the Quinta da Regaleira—an enchanting estate riddled with freemason symbols and mythological motifs throughout its chapel, gardens, and underground tunnels. Before returning to Lisbon, drive along the sheer seaside cliffs of the Sintra-Cascais Natural Park to Cape Roca, the westernmost point of continental Europe.
Travel to the medieval city of Évora, capital of the Alentejo region and a World Heritage site. Wander the old town with a private guide, stopping at the fortress-like cathedral and the 16th-century São Francisco Church, featuring nautical motifs celebrating the Age of Discovery and a chapel decorated with human bones and skulls. Continue to the University of Évora, founded as a Jesuit seminary in the 16th century, then see the first-century remains of the Roman Temple. Enjoy the rest of day at leisure, choosing to relax at the hotel or continue your exploration of the city.
After breakfast, enjoy a private transfer to postcard-perfect Marvão. Perched atop a craggy granite peak in the São Mamede Range with sweeping views of the Alentejo plains, Marvão—named for a Moorish chieftain—was historically used as a defensive fortress. Explore the charming, white-washed village on your own and climb up to its towering 13th-century castle. Continue to Sortelha, one of Portugal’s best-preserved medieval villages, en route to Marialva.
This morning, discover the hilltop village of Castelo Rodrigo and the majestic city of Trancoso, rife with history since the Middle Ages. Return to your hotel in Marialva in the afternoon, then venture out to the World Heritage–listed Côa Valley, home to some of the world’s most important prehistoric rock art. Enjoy a private night tour of the valley’s greatest concentration of Paleolithic engravings with a local expert and observe how layers of art appear in the shifting shadows.
Today, travel through the lush terraced landscapes of the Douro Valley on your way to Porto. Visit the picturesque village of Pinhão before continuing to the Quinta do Crasto wine estate. Tour the sun-soaked vineyards and enjoy lunch and a wine tasting overlooking the Douro River. Then transfer to the city of Porto, known for its production of port wine. Spend the rest of the day on your own, strolling Porto’s colorful waterfront or stepping into its baroque churches. Or visit Livraria Lello, the beautiful bookshop said to have inspired author J. K. Rowling’s description of the Hogwarts library.
Set out on a private walking tour of Porto’s World Heritage-listed historic center—a network of cobblestone streets, antique storefronts, and charming squares. Visit the Church of São Francisco, a Gothic landmark harboring a lavishly gilded interior, and the Bolsa (or Stock Exchange) Palace, notable for its granite work and opulent Arabian hall. This afternoon, explore Porto at your own pace. Delve into Serralves Park, an exquisitely landscaped green space sheltering tranquil ponds, fountains, and modern sculptures. Or stop by the futuristic Casa da Música, one of the city’s leading concert halls, and wander its labyrinth of stairs, corridors, and eclectic rooms.
Transfer to the airport for your flight back home.