Portugal's Historic Cities: A Tailor-Made Journey to Lisbon and Porto

Arrive in Lisbon, and meet your private driver at the airport for the transfer to your hotel. After time to settle in, head to a fado restaurant for a special dinner accompanied by a live performance of Portugal's traditional melancholic fado music. (D)

Get to know Lisbon today with a guided walking tour of the city's highlights, exploring the  beautiful Bairo Alto neighborhood and the lively streets of the Chiado, lined with historic shops and bustling restaurants. Along the way, taste a variety of Portuguese delicacies and learn how they fit into the city's history and traditions. During free time after your tour, we recommend a visit to the waterfront Belém neighborhood, home to the Jerónimos Monastery and the Tower of Belém. (B)

Meet your private driver this morning and venture out to nearby Sintra, a town of misty forests and lavish palaces that tells the story of Portugal’s past. Once inhabited by the ancient Celts, who found it to be a place of spiritual power, Sintra bears traces of its Moorish occupation and its days as a 19th-century resort that enchanted famous travelers such as Lord Byron. Explore the sites of the town as you wish today. Venture to the ornate Quinta da Regaleira, steeped with mysticism and surrounded with hidden grottos and lush gardens. Step into Portugal’s royal history on a tour of the National Palace or ascend to whimsical Peña Palace, an extraordinary confection of Romanticist architecture in the hills above the town. You might also opt to hike to the ruins of the Moorish castle where you can climb the ramparts for a view all the way to the coast. Enjoy free time back in Lisbon this afternoon. Our suggestion: climb up to Castelo São Jorge for breathtaking views of the city at sunset. (B)

Head north by train to Portugal's second city, Porto, set on the steep banks of the Douro River and known as the center of the port wine industry. Upon arrival, you'll be met and driven to your hotel. Enjoy the rest of the day to explore the city on your own. Consider taking a walk along the quay or pay a visit to the Serralves Museum of Contemporary Art to admire its art and architecture. (B)

Embark on a full-day panoramic tour of the city with a private guide, followed by a port wine tasting. Begin by exploring the city's historic heart on foot, passing landmarks such as the Sé Cathedral and the São Bento train station, where elaborate azulejos, or blue-and-white painted tiles, depict scenes from Portugal’s history. Stroll through the old town to the riverfront and see the Dom Luis I bridge, designed by a student of Gustav Eiffel. Then hop in a car to drive down to the bustling waterfront at Foz do Douro, where the Douro River meets the Atlantic. Cross the river to the Serra do Pilar viewpoint for expansive views of Porto and its bridges and the Atlantic coast. Continue to the port lodges of Vila Nova de Gaia, just across the river from the city. Take a guided tour to learn about Porto’s long tradition of port production, and enjoy a tasting of the lodge’s different vintages. (B)

East of Porto, the vineyard-covered slopes of the Douro River Valley have produced port wine grapes for 2,000 years. Spend a full day discovering this landscape, named a World Heritage site for the terraced vineyards that represent many centuries of agricultural evolution. This beautiful area is wonderful to visit from the vineyards themselves. Set out on a tour of several wineries, learning about their winemaking traditions and sampling the wines and ports they produce. Enjoy a lunch of local specialties in one of the wineries and take an easy hike among the vineyard covered slopes if you wish.  Head back to Porto this afternoon, enjoying the scenic drive through the Douro River Valley. (B,L)

After breakfast, make your way to the Porto airport for your flight home. (B)