Curator’s statement
Portugal is a year-round destination known for its exceptional food, wine (and port!), rich culture, and layered history. Whether you arrive with a thoughtfully planned itinerary or prefer to explore as you go, it’s an easy and rewarding place to navigate. Ideal for a long weekend from the East Coast or a more immersive, longer journey across the country, Portugal offers flexibility without sacrificing depth. Having experienced it both ways, each trip feels entirely its own, and equally memorable.
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Day 1: Arrive & explore

Exploring via tuktuk
Land in Lisbon, drop your bags at the hotel, and head straight to Time Out Market for lunch. From there, take a scheduled or impromptu tuk-tuk tour to get a feel for the city. In the evening, enjoy a delicious dinner at one of José Avillez’s restaurants—we loved Páteo, but he has a number of great options depending on how casual or elevated you want the night to feel.
Day 2: Culinary journey

Snacks on the food tour
Start your day with a food and wine tour of the city—it’s one of the best ways to get oriented while tasting some of Lisbon’s highlights. My favorite bite I’ve ever had in Portugal was the bifanas from my walking food tour on my first visit. In the evening, lean into the culinary theme and take a private Portuguese cooking class.
Day 3: Belém icons & LX Factory

Mosteiro dos Jerónimos
Spend the morning in Belém visiting Mosteiro dos Jerónimos (one of the most beautiful sites in Portugal). Afterward, stop at Pastéis de Belém for their famous pastéis de nata. In the afternoon, head to LX Factory, a creative, industrial-style complex filled with shops, cafes, and galleries. It’s a great place to wander, pick up a few unique finds, and grab a casual drink before heading back to your hotel. Enjoy dinner at Rocco for Italian fine dining—make sure to order the tagliatelle in a pecorino cheese wheel.
Day 4: Fairytale day trip to Sintra

Palácio Nacional da Pena
Take a day trip to Sintra (easily accessible by private car, Uber, or train). Be sure to book tickets in advance for Palácio Nacional da Pena. Have lunch at Pizzeria do Carmo, then visit one or two of the other castles—Quinta da Regaleira, Moorish Castle, Sintra National Palace, or Monserrate Palace. Head back to Lisbon for dinner at the classic Portuguese bistro Cervejaria Trindade.
Day 5: Journey to the Douro Valley via Nazaré

Douro Valley view
Have a driver take you to the Douro Valley, stopping in Nazaré along the way to see the famous waves and grab lunch. Watch the surf from Forte de São Miguel Arcanjo, and definitely check the wave forecast ahead of time. Settle into your private villa in the Douro Valley in the late afternoon and enjoy a relaxed dinner prepared by a private chef.
Day 6: Douro Valley wine & views

Tasting at Quinta De La Rosa
Start your morning with a tour and wine tasting at Quinta de la Rosa, followed by one of the most beautiful lunches at Cozinha da Clara. In the afternoon, head to Quinta do Seixo for a port tasting where you’ll learn about the production process and taste a range of ports. End the day with dinner at Writer’s Place in Pinhão—a small, family-owned spot that’s truly special.
Day 7: River cruise in Porto

6 Bridges River Cruise
Head to Porto via a car service, check into your hotel, and head out for a private boat ride to see the city’s six bridges. Enjoy Portuguese wine, cheese, and meats on the water. For dinner, try Tapabento, Flow, or Mistu.
Day 8: Porto highlights & port tastings

Port cellar tour and tasting
In the morning, visit Livraria Lello—the Harry Potter lookalike bookstore—for a quick stop (be sure to book tickets in advance). If you’re up for it, climb the Clérigos Tower for views over the city. Wander down to the Ribeira and grab lunch along the water.
In the afternoon, do a port cellar tour and tasting in Vila Nova de Gaia—great options include Taylor’s Port, Graham’s Port Lodge, or Sandeman. Finish with a final dinner at Alto Porto.
Need to know
Uber works well in Lisbon and Porto and is often easier than taxis.
Have some cash on hand for smaller restaurants and cafés.
Hiring a driver between Lisbon and Porto is the easiest and most comfortable option (and allows for stops along the way).
Flying into Lisbon and out of Porto makes the itinerary seamless and avoids backtracking.
Book major sites like Palácio Nacional da Pena and Livraria Lello in advance—they sell out and lines can get long.
Comfortable shoes are a must—Lisbon in particular is very hilly with cobblestone streets.
If doing the Douro Valley, I strongly recommend pre-booking tastings—many of the best quintas require reservations.
Don’t overpack your days—Portugal is very much about wandering, long meals, and enjoying the pace.

Travel Advisor
Megan McLaughlin
Megan McLaughlin
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