Portugal with Chris McDade & Natalie Grindstaff

Welcome to Lisbon! We’ll breathe in the salt air and take in the atmosphere of the Portuguese capital’s unforgettable pastel buildings. Travel is the great educator—and for Portugal, we begin by immersing ourselves in learning local traditions. First, we wander through the historic district of Belém, stopping at a local factory whose bakers have followed an ancient recipe of delectable custard tarts from the monks of Mosteiro dos Jerónimos since 1837. We’ll go behind the scenes with a hands-on lesson in making these traditional wedding pastries and, of course, to eat them! Afterwards we meet up with local artists to try our hand at creating another Portuguese icon: the distinct azulejo tiles that beautifully adorn doorways and walls.

Our welcome dinner tonight is a special treat: a local feast with signature drinks and an unforgettable live Fado performance, where we’ll revel in what’s been the “soul of Portuguese music” for two centuries.

Today we move into the world’s most scenic wine region, stopping along the way to peek through two windows of traditional rural life. One hour from Lisbon, we’re greeted by the orange terra-cotta rooftops of the village of Óbidos, a town with Roman roots and a medieval layout with horse carriages and bookshops along its cobbled lanes. We’re here to sip the country’s best ginja, a traditional sour cherry liqueur.

Next we move to the winery and vineyards of Filipa Pato and William Wouter, a husband-and-wife team producing award-winning biodynamic Bairrada wines, the rich and deeply colored reds made from indigenous Baga, Castelão and Rufete grapes. Filipa will share her passion and winemaking knowledge as William, the chef and sommelier, crafts an impeccably paired five-course lunch for us.

After lunch, we reach our breathtaking riverside base, deep in the Douro Valley. Here we’ll rest riverside with a glass of Port, dusk fading into a starlit evening, and regroup for dinner—and a toast—to our new home.

After morning coffee and breakfast overlooking the river, we’ll assume the life of an 18th-century Portuguese trader. Jump aboard a flat-bottomed Rabelo boat and we’ll head upriver. It’s a timeless experience—sit back, listen to local accordion players and enjoy the gentle ride to Adega Maçanita winery. Here, we’ll go behind the scenes with in-house enologists and taste directly from barrels.

After lunch—paired with local wines, of course—the afternoon and evening are all yours. Relax poolside at the hotel on the Douro River, spend time with your fellow travelers on the patio as the sun sets. For the more intrepid, take in local art with an evening stroll through the riverside town of Pinhão, famed for tile-covered bridges.

We’ve sampled Portugal’s history, impeccable wines, and culinary classics. Today our connection with the region’s roots go deeper—and more literal—on a fun day of creating, learning and celebrating with Chris and Natalie. We’ll collect and harvest the ingredients we need for a glorious lunch, then head to Casa dos Viscondes das Várzea, a 17th-century manor house owned by a local female chef. Here, surrounded by vineyards and olive groves, we’ll roll up our sleeves and help Chris and Natalie create an unforgettable meal (hands-on and learning as we go) using our hand-picked ingredients and locally sourced wines. The reward? Our very own al fresco feast, prepared in a setting worthy of its own landscape painting or glossy magazine cover!

For centuries the Douro Valley has been synonymous with port wines. We’ll end this magical day with a modern twist, tasting award-winning ‘dry’ reds and whites with the same grapes that have traditionally only been used for ports. After a glass or three, we’ll return to our hotel for an easygoing late afternoon to explore and rest on our own.

Our Portuguese adventure moves along with the Rio Douri, to the charming seaside city of Porto. En route it’s gorgeous gardens, vineyards that stretch for miles—and tinned fish! In Matosinhos, a classic industrial neighborhood on Porto’s outskirts, we’ll have an exclusive look at legendary cannery Pinhais & Cia, specialists in sardines since 1920. The best local catch, the freshness ingredients, homemade secret recipes perfected for generations—this is the pinnacle of artisanal tinned fish in Portugal.

After lunch on Matosinhos’ seafront, we’ll arrive in central Porto and ride tuk-tuks through the city’s narrow, cobbled alleyways while taking note of which neighborhoods, markets, and cafes to visit in our free time. Dinner tonight is at a local tapas restaurant sampling just-caught bacalhau (cod), Bulhão Pato-style clams, and other traditional Porto seafood dishes.

We start our full day in Porto on foot, with a tour through the streets of Old Town, ducking into small cafes, tascas (taverns), and colorful food markets. We’ll watch fishermen arrive, nets full with the catch of the day, and decipher the tales told of Porto’s ceramic azulejo tiles adorning churches and subway station walls. After relaxing over a leisurely tapas lunch together, the afternoon is yours to explore—sit by the sea, shop for mementos, or people-watch in the UNESCO World Heritage Ribeira District. 

Tonight, we’ll gather for a private farewell feast at W&J Graham’s, its 19th-century cellars stocked with 3,000 barrels of gently aging wines. We’ll toast our time together with Chris and Natalie over vintage ports and plates of fresh seafood and local meats, with views over Porto and the Douro River. It’s the ideal setting for our joyful farewell.

After our final breakfast at the hotel, we bid farewell to Chris and Natalie and our fellow travelers—hearts and spirits full of all things Portugal. Then it’s off to the airport. Until next time! Obrigada e adeus, Portugal!