Because of its relatively warm temperatures (in the 50s) and small crowds, Paula Oliveira, executive director of Turismo de Lisboa, calls winter “a perfect period to come for a short break.” She recommends visiting at Christmas or New Year’s, when you can sample specialty pastries and witness the city’s sparkling and festive city lights.
You could probably spend an entire week simply wandering Lisbon by foot or streetcar, but I recommend a food and wine walk with the tour group Inside Lisbon. On our three-hour excursion, we sampled pastel de nata and espresso, cheese and port, and bacalhau (salted cod) and green (referring to its age, not its color) wine, learning about the city’s culture and history with each bite. For more yummy eats, check out restaurant Ze da Mouraria and the Time Out Market.
When you’d like to escape the city, travel an hour northwest by train to Sintra. This small town, a UNESCO World Heritage site, is filled with castles. Among the most notable are the National Palace of Pena, a colorful 19th-century building that looks like it’s straight out of a Disney movie; the Castle of the Moors, a hilltop fortress with gorgeous views of the surrounding valley; and the Quinta de Regaleira, a Gothic mansion with expansive gardens.