One Week in Porto, Lisbon, and Madeira
A dream for urban explorers, culinary aficionados, and nature lovers alike, Portugal offers countless opportunities for cultural discovery and spiritual rejuvenation. One of Europe’s oldest cities, Porto will charm visitors with its historical sites, world-class culinary scene (after all, it’s the birthplace of port wine), and natural wonders, thanks to its location on the Douro River. It’s also just minutes away from the quaint coastal city of Vila do Conde, which proves to be much more than a sleepy beach town with its rich maritime history and cultural gems. For stunning views, walkable streets lined with colorful buildings, and fresh seafood, look no further than Lisbon, the City of Seven Hills. And round off your trip with a stop in Madeira, nicknamed the Hawaii of Europe because of its dramatic landscapes and lush vegetation. (To customize this itinerary or explore another destination, reach out to The Jeffset here.)​
Days 1–3: Porto and Vila do Conde
Stay
Your adventure begins with a quick 20-minute drive from the Porto Airport to the Lince Santa Clara, your home base for the next few days. Once a 14th-century monastery, the hotel is located in Vila do Conde and marries contemporary design with neoclassical charm through the work of visionary architect Carvalho Araújo.
With two outstanding restaurants (including the Mosteiro, where you can enjoy Portuguese specialties from local chefs, and Oculto, a Michelin-starred fine-dining concept), two bars, an open-air infinity pool, and a Sisley spa equipped with a Turkish bath, the Lince makes it easy to rejuvenate without you having to take a single step outside its doors.
Eat and Drink
Located on the upper level of the Gran Cruz House, a stylish boutique hotel in a 17th-century building, Casario serves up contemporary Portuguese cuisine (think scallops with saffron, lemon rice, and avruga caviar) alongside stunning views of the Douro River. Patrons also have an extensive wine cellar to choose from, with over 60 varieties on offer.
For hearty casual fare, stop by Café Santiago, which reportedly serves one of the best sandwiches in the world. The Francesinha sandwich, a Porto classic, features layers of meat and cheese and is drowned in a spicy sauce made with tomato and beer.
​
Casa de Chá da Boa Nova, a few minutes’ drive from Porto, offers a feast for all senses. Housed in a former teahouse designed by acclaimed architect Álvaro Siza Vieira, the seafood restaurant is perched on a rocky cliff that overlooks the Atlantic, so guests can take in the sweeping landscape while tucking into lobster, cuttlefish, and other culinary delights from executive chef Rui Paula.
Do
Walk the streets of Porto with an expert as your guide: They’ll take you through the city center along Avenida dos Aliados, the central thoroughfare lined with architecturally striking hotels, banks, boutiques, and cafés. You’ll marvel at the Igreja de São Francisco and the Palácio da Bolsa, a former stock market, and take in the sweeping views at the Ponte de Dom Luís I, the famed double-deck bridge that spans the Douro River.
Literary types and architecture lovers will relish a visit to Livraria Lello, a neo-Gothic bookstore that’s been enchanting patrons since the early 1900s (and believed by some to have inspired the Harry Potter books). Get exclusive access to the Sala Gemma, a space devoted to the bookstore’s most prized gems, including rare books, manuscripts, and first editions.
Join a local culinary expert for an exploration of Porto’s food scene. You’ll have the opportunity to sample artisanal cheeses and charcuterie crafted by local small-scale producers; pop into beloved pastry shops, taverns, and snack bars; and get a taste of Portugal’s famous convent sweets. And of course, you’ll top it all off with a tasting of the region’s celebrated port wine.
Get a glimpse into Vila do Conde’s rich maritime history with a visit to Museu de Construção Naval, where you’ll learn about the city’s shipbuilding tradition through hands-on exhibits and even a full-size replica of a 16th-century ship.
Days 3–6: Lisbon
Stay
The next stop in your journey is a quick (and scenic) two-and-a-half-hour train ride away. Once you arrive at Gare do Oriente—designed by world-renowned architect Santiago Calatrava and one of Portugal’s most stunning landmarks—your driver will be waiting to take you to your accommodations.
While Lisbon offers no shortage of charming hotels, the Torel Palace Lisbon dazzles with unparalleled views of the city (thanks to its vantage point on one of the city’s seven hills), old-world opulence, and five-star amenities, including 2Monkeys, a 14-seat Michelin-starred restaurant; two outdoor pools; and a serene spa.
Eat and Drink
No trip to Lisbon would be complete without a pastel de nata, the iconic Portuguese egg custard tart. After a visit to the Jerónimos Monastery—a UNESCO World Heritage site—walk just a few hundred meters and grab a fresh-baked tart at Pastéis de Belém, which uses a closely guarded recipe first developed centuries ago by monks at the monastery.
Ofício, located in the lively Bairro Alto district, considers itself an “atypical tasco,” but it’s more reminiscent of a chic gallery than a Portuguese tavern. Come for the inventive shared plates—like tuna and chipotle lettuce tacos and cod with roasted potato foam—stay for the low-key vibes and stunning interiors.
Since opening in 2017, Prado has led the farm-to-table movement in Lisbon, serving inventive dishes inspired by local ingredients (e.g., smoked eel with caramelized onion rice and chicken skin and mushroom ice cream garnished with caramel and crunchy barley). The menu rotates frequently, a testament to how chef Antonio Galapito embraces the seasons in his culinary approach.
Do
Wander the labyrinthine streets of the Alfama district, the oldest neighborhood in Lisbon (and all of Portugal), where you can uncover hidden courtyards, take a ride on the 28 tram, and stop for a snack at the Scandi-chic Copenhagen Coffee. You’ll also want to swing by São Jorge Castle, the National Pantheon, and the Romanesque Lisbon Cathedral while you’re in the area.
Housed in a former convent, the Museu Nacional do Azulejo pays tribute to Portugal’s rich cultural history, specifically the craft of glazed tiles. Visitors can marvel at over 300 pieces, including the Our Lady of Life panel, which was reportedly painted by Marçal de Matos, one of the first azulejo artists, in the late 16th century.
Sintra is just 40 minutes by train from Lisbon, but it feels worlds away: Quaint gardens, ancient palaces, and cobblestone streets contribute to its fairy-tale-like charm. A major center for European Romantic architecture, Sintra is home to Ferdinand II’s Pena Palace, a colorful monastery-turned-castle surrounded by lush greenery and winding paths.
Days 6–8: Madeira
Stay
The last leg of your journey will take you to Madeira, a two-hour flight from Lisbon. The five-star Savoy Palace, an elegant blend of modern sophistication and old-school glamour (see the grand staircases in the lobby and shiny grand piano in the bar), is the ideal landing pad from which to explore the island’s many natural marvels. Before checking out, be sure to stop by the forest-inspired spa—the largest spa in all of Portugal—and one of the nine on-site restaurants and bars, including Galáxia Skyfood, the intergalactic-themed fine-dining concept.
Eat and Drink
Madeira native Octávio Freitas’s knack for imaginative seafood dishes is on full display at the Michelin-starred Desarma. Diners will be equally impressed by the extensive wine selection (Desarma has one of the finest collections of Madeira wines) and sweeping views, courtesy of the restaurant’s location on the top floor of The Views Baía hotel.
For an authentic Madeiran dining experience, check out Bela 5 Snack Bar, a casual eatery known for its seafood. Every dish is simple but well-prepared—and the perfect way to refuel after a hike on one of Madeira’s many rugged trails.
At 5 Sentidos, you’ll find a tightly curated menu of contemporary Portuguese fare, made with the freshest ingredients of the highest quality and served in a warm, intimate setting. (We recommend trying the octopus made with honey and spices.)
​
Do
Whether you seek lush tropical greenery or rugged volcanic terrain, Madeira is a hiker’s paradise, with hundreds of trails ready to be explored. The Vereda da Ponta de São Lourenço, also known as the Dragon’s Tail, is among the most iconic hikes on the island and takes you along the easternmost peninsula, with panoramic ocean views and distinct rock formations.
Traverse Madeira’s gorgeous winding roads in style with a sidecar tour. You’ll witness some of Madeira’s most beautiful views as you make your way to Câmara de Lobos, a small fishing village once frequented by Winston Churchill. There you’ll get to sample poncha, a traditional Madeiran drink made with rum, honey, and fruit.
With a private yacht tour, you’ll have the opportunity to explore Madeira’s breathtaking coastline, including secret coves and beaches accessible only by sea. Meet at the Quinta do Lorde marina, on the easternmost point of the island, where you’ll board the luxurious Princess V58.