Portugal with Jonny & Monique Black

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 time at the table.

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.

The afternoon is yours to settle into Lisbon at your own pace. Perhaps wandering the tiled streets, lingering over a glass of vinho verde at a shaded café, or watching the late-day light spill across the Tagus is on the agenda before we gather again for dinner.

Dinner tonight is at a Lisbon institution that’s been beloved since 1947. Beneath the glow of polished brass and white tablecloths, the menu is likely to offer the epitome of Portuguese seafood culture: platters of scarlet prawns, garlicky clams, and towering crab straight from the Atlantic.

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

Along the way we’ll stop in Obidos, a picturesque town encircled by medieval stone walls. Once presented by King Dom Dinis to his queen as a wedding gift, it feels suspended somewhere between folklore and history, still carrying that sense of romance today.

After, 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 at a nearby restaurant.

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 yours to embellish, but don’t worry, we’ll provide plenty of recommendations.

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.

We’ll enjoy lunch at the vineyard, with sweeping views of the river, before catching a train back to the hotel for some downtime. As dusk settles, we’ll reconvene for a meal unlike anything else we’ll eat in Portugal. Conversations stretch between bites of rustic fare and sips of tawny blends as deeply regional flavors come to life in the glow of wood-fired ovens. It’s 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 few nights. Before settling in for the evening, we’ll explore on foot, 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. Along the way, we’ll sample some of the most iconic dishes of Porto for dinner.

Today, we head to Matosinhos, an industrial quarter on the fringes of Porto, where the Atlantic still shapes the cadence of daily life. Once there, we’ll enjoy a glimpse into Portugal’s northern canning industry through tiled streets and working harbors lined with fishing boats returning from sea. We’ll stop at a family-run sardine cannery dating back to 1920, where generations of craftsmanship unfold by hand, from the careful preparation of each fish to the final paper wrapping. before we sit down to taste the briny, olive oil-rich preserves that have long defined this stretch of coast.

In the afternoon, we’ll have lunch together at a nearby restaurant and then you’ll have time to return to the hotel before enjoying dinner on your own.

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, 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 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!