Today, we’ll explore the city’s backstreet eateries and food markets, searching for clues to its rich history. Our day begins at a classic pastry shop next-door to the 18th-century Estrela Basilica. As we munch the famous convent pastries, we’ll be transported to the era when Lisbon was at the epicenter of the spice trade. From there, we’ll head up to the Campo de Ourique district, a “city within a city,” where we’ll enjoy a series of traditional Portuguese bites around the bustling market. We’ll also descend into a bookseller’s secret basement, which stocked contraband literature during the 20th-century Salazar regime. For lunch, we’ll visit a neighborhood association with an intriguing political past, and have a chance to ask questions and rest our legs. In the afternoon, we’ll descend into the historic underground water tunnel network, which once brought water to the city’s fountains. Emerging above ground at a most unusual wine bar, we’ll cap off the day with a port wine tasting. Take the rest of the evening to rest and relax or explore further on our own.

Today, we’ll dive into Lisbon’s port district to learn about the city’s deep affinity for the sea. We’ll begin in the historic dockside neighborhoods, stopping for a visit to a third-generation coffee roaster to sample the wood-fire-roasted goods. We’ll wind our way through the cobblestone alleys to the lavishly tiled Convento das Trinas do Mocambo, a former convent now home to the navy’s Hydrographic Institute. We’ll lunch at a charming fish restaurant tucked away in the docks, before boarding the bus and heading about 45 minutes along the coast to the Colares region near Sintra, home to Europe’s westernmost wine region. We’ll visit Viuva Gomes, a wonderful family-run winery, then, keeping with the theme of the sea, we’ll enjoy an early dinner at a classic waterfront seafood restaurant with views over the Atlantic. If you still have energy upon our return to Lisbon, you can head out to explore the city after dark.

Take a leisurely morning to relax or wander on your own. In the early afternoon, we’ll reconvene to try our hand at the crown jewel of the Portuguese pastry pantheon: the pastel de nata. We’ll test the nimbleness of our fingers during a hands-on workshop in a local bakery, then have the chance to sample our custand delicacies. We’ll enjoy a quick respite gathering for a multi-course Goan feast at Jesus é Goês. The ever-boisterous chef, Jesus, will guide our culinary experience, explaining how each dish embodies centuries of Portuguese-Goan relations.

After a quick breakfast at the hotel, we’ll get an early start and drive out to the Alentejo region, southeast of the city. At a traditional farm, we’ll learn to bake the region’s signature loaves of bread, and then we’ll head out to the fields to learn about the local olives, cork production, and Iberia’s famous black-hoofed pigs. We’ll have a relaxed lunch with the farmers and enjoy a chance to ask them about their local specialties. We’ll then continue with a visit to a local wine producer to learn about the tastes and tannins of this lesser-known wine region. The winemaker will join us for dinner—a delicious spread featuring the region’s distinct cuisine. Bellies full and glasses empty, we’ll return to Lisbon for a good night’s sleep.

July departure only: This morning we’ll head south out of Lisbon to the center of Portugal’s fishing industry, Setubal. Known today for its lively fish market and tinned fish factories, the industry is rooted in Roman times, back when this area was the biggest producer of the garum, that funky fermented fish sauce beloved by the Romans. We’ll visit the fish market and have a refreshing local lunch of spanking-fresh fish. We’ll then take the ferry across the Sado estuary to the Troia Peninsula, where we’ll visit the Roman ruins with local archaeologists. We’ll learn about garum production and even have a taste of it during our picnic among the ruins. (By the way, there’s a good swimming spot right nearby—though there isn’t a changing room, you can definitely still bring a swimsuit and towel for a dip!) In the late afternoon we’ll head back to Lisbon, where you’ll have the evening free to rest, relax, and explore on your own.

This morning, you’ll be free to zip or wander around the city on your own. After lunch, we’ll meet up at the hotel, where a historic tram will be waiting to whisk us off. We’ll ride through the city’s winding streets, stopping into a number of local cultural institutions to hear their stories. Over a quick drink, we’ll meet the people keeping these institutions vibrant and possibly be treated to a performance. We’ll then tuck into a delicious farewell meal at a contemporary Portuguese restaurant, celebrating our final night in Lisbon over local wines and fresh takes on classic fare.