Portugal Tour with Gus Stieffenhofer-Brandson & Mandel Hitzer

Welcome to Lisbon, the ancient city that seems to drift in the salt-tinged breeze and home to azulejo tiles, winding cobblestoned alleys and charming pastel buildings. We’ll start in the afternoon with cocktails at a local bar, and just as the sun begins to set, we’ll begin our journey in the only sensible way—in true Portuguese style, with a local supper and an unforgettable live Fado performance, where we’ll revel in what’s been the “soul of Portuguese music” for two centuries.

We begin by immersing ourselves in Lisbon’s daily bustle: wandering through the historic district of Belém where landmarks like the Belém Tower and Mosteiro Dos Jerónimos stand as magnificent architectural marvels. If you’re suddenly tantalized by the aroma of custard tarts, there’s no need for alarm; for decades the Pastéis de Belém have drawn travelers from the cobbled streets and into their modest bakeries.

In the afternoon, we point our compass to the outskirts of town. Described by Hans Christian Anderson as the “most beautiful place in Portugal,” the village of Sintra, a World Heritage Site, is where we venture today. With a castle that seems to float in the clouds, Sintra has a mystical feeling, like stepping into a fairy tale or back in time. Portuguese nobility has historically kept residences here, and around every corner, there’s a different architectural wonder to behold. During our exploration, we’ll see sweeping views stretch to the Atlantic from its terraces, and while inside, lavishly adorned rooms reveal the romantic grandeur of Portugal’s 19th-century royalty.

After, we’ll wind our way back to Lisbon, where dinner tonight is yours to embellish.

Today, we head north towards one of the world’s most scenic wine regions, the Douro Valley.

Along the way, we’ll visit a family winery known for its rich and deeply colored reds made from indigenous Baga, Castelão and Rufete grapes. We’ll taste through the vineyard and settle in for a lunch of local vegetables and traditional suckling pig.

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, as we check into our next abode. Dinner tonight is a quintessential Portuguese feast at a beloved local establishment.

After 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 a lovely riverside winery. Here, alongside local winemakers, we go behind the scenes at the vineyard and taste directly from barrels.

After lunch—paired with local wines, of course—we’ll return to our hotel for an easygoing late afternoon, only to reconvene for a meal unlike anything else we’ll eat in Portugal. Seated at a long communal table, surrounded by the vines that produced the wines in our glasses, each course is seasonal, regional, and thoughtfully paired with acclaimed port and Douro wines. As dusk settles, conversations stretch between bites of rustic fare and sips of tawny and vintage blends, making for an evening that feels both intimate and timeless.

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 memorable day of creating, learning and celebrating with our tastemakers and hosts.

We’ll learn local cooking techniques while we enjoy a splendid lunch at an elegant 18th-century manor house. Our efforts will culminate in a rewarding al fresco feast, set against a backdrop reminiscent of a captivating landscape painting or the pages of a glossy magazine.

After we eat, we’ll make our way to the beautiful city of Porto, our home for the next two nights. Before settling in for the evening, we’ll glide along the Douro River in a Tuk Tuk, winding through Porto’s cobbled streets and sun-drenched hillsides, passing storied facades, centuries-old churches, and hidden alleyways steeped in history. It’s a lively, intimate way to take in the city’s layered past and vibrant present. Afterward, the rest of the evening is on your own, but don’t worry, we’ll provide plenty of recommendations for dinner.

We’ll start the day with a slow morning—perhaps a leisurely breakfast at the hotel or a bit of shopping is on the agenda. After a bit of relaxing, we’ll dive into a food and culture tour in Old Porto. Not only will we sample regional delicacies, but we’ll also explore the nuances of cafes, delis, and restaurants and their particular significance in the city. Along the way, we’ll watch fishermen arrive, nets full of the catch of the day, and decipher the tales told of Porto’s ceramic azulejo tiles adorning churches.

After a light lunch, we’ll travel across the river to Vila Nova de Gaia to learn about the history of Port wine, the wine-making process at one of the world’s most iconic Port producers stocked with 3,000 barrels of gently aging wines, and enjoy a tasting in a private room to understand it’s fascinating history and how this fortified wine changes over time.

In the afternoon, you’ll have time to return to the hotel before we regroup for the evening.

The menu for tonight is a tapas dinner filled with creative dishes that resonate with Portuguese history and flavor combinations unique to Porto and the Douro Valley.

After a morning at leisure, we roll up our sleeves for a special pastry class. We’ll go behind the scenes with a hands-on lesson in making pastel de nata–traditional wedding pastries, sampling as we learn, of course.

Afterward, the afternoon is yours to unwind, explore, or enjoy a quiet lunch on your own.

Tonight, we’ll raise one last glass together alongside a Michelin-starred menu that celebrates the richness of Portugal’s cuisine and the stories behind its most iconic ingredients. Over vintage ports and plates of fresh seafood and local meats, with views over Porto and the Douro River, we’ll toast to our time together in a joyful farewell.

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