Portugal with Rob Rubba

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 the hotel, 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.

We’ll settle in for dinner in the historic center of town, and after several courses of farm-to-table cuisine, we’ll wind our way back to Lisbon.

Today we move into the world’s most scenic wine region, for an enchanting farm-to-table experience.

We’ll visit a family farm in Santarém known for its environmentally friendly practices. We’ll discuss sustainability and take a captivating tour exploring the sprawling grounds, before settling in for a lunch of hand-picked produce and other local ingredients.

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, dinner is on your own tonight.

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. Centered around expansive wood-burning ovens, Bomfim 1896, helmed by Pedro Lemos, conjures the essence and aromas of an authentic Douro kitchen—during the meal, we’ll take a moment to reflect on the day and toast the adventure ahead.

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 tastemaker and hosts.

We’ll learn local cooking techniques while we enjoy a splendid lunch at an elegant 17th-century manor. 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. The evening is on your own. See you in the morning.

We dive straight in to the bustle with a Tuk Tuk tour along the river which flows right through the city’s historic center. After taking in some breathtaking architecture and getting a sense of the city, we dive into a food and culture tour in Old Porto—not only will we sample regional delicacies, but we’ll explore the nuances of cafes, delis and restaurants and their particular significance in the city.

In the afternoon, we’ll slip into a local tasting room and sample some crisp Alvarinho before returning to the hotel to relax.

Dinner tonight is refined at one of Portugal’s plant-based restaurants. Get ready for creative dishes that resonate with Portuguese history and flavor combinations unique to Porto and the Douro Valley.

After a morning at leisure, we head to a local oyster farm, where you’ll step into the life of an oysterman. On a guided tour, learn firsthand about sustainable techniques used to cultivate plump, flavorful oysters. Hear stories of early mornings on the water, the quiet rhythm of tending to oyster beds, and the delicate balance of nature that produces these prized shellfish. Taste the difference for yourself as we enjoy freshly harvested oysters for lunch, a true reflection of Portugal’s coastal bounty.

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 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 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!