Essential Lisbon: A 4–Day Itinerary

If you’re flying from the U.S., your arrival in Lisbon will likely be anywhere from early to mid-morning, just in time to catch the breakfast buzz. Reward yourself with your first espresso and pastel de nata–they will be the first of many!

After dropping your luggage off at your hotel (or checking with that that early check-in perk!), consider joining a city walking tour or a TukTuk sightseeing tour. This will give you a nice introduction to Lisbon’s historical downtown area and will keep you going for a couple of hours. I always find it easier to do some sightseeing on arrival and turn in early in the evening to beat out that jetlag.

Consider checking out Baixa Lisboa, with its popular Rua Augusta, Rossio Square and Carmo Convent which doubles as an outstanding archaeological museum. If by evening you’ve had enough espresso to give you that extra boost of energy, consider checking out Bairro Alto district. Here you’ll find bars, restaurants and clubs across all budgets and tastes. If you’re looking for something a bit more traditional, be sure to pop into a fado house for a live performance and glass of wine.

Alfama is the oldest, and hands down most charming district of Lisbon. Because it escaped the damage from the 1755 earthquake and fire that destroyed much of downtown lisbon, what you see today dates back centuries.

Take some time to wander through labyrinth streets and make your way up to St. George’s Castle. While one of the most popular ways of reaching the castle is aboard Tram 28, unless you’re visiting off season, the wait may not be worth it. The castle can get busy, especially in the summer months, but it never feels overly crowded once you’re inside the walls. Insider Tip: buy your tickets online to skip the ticket booth queue.

Adjacent to Alfama is the quaint district of Mouraria, birthplace of Fado music. Monastery of São Vicente de Fora is nearby, with its 16th century blue and white azulejo adorned cloister. It’s a bit off the beaten path which can be a nice respite from the crowds. Fans of flea markets and antiquities should make a detour to Feira da Ladra, which runs on Tuesdays and Saturdays behind the monastery.

Both Sintra and Óbidos are super popular day trip destinations from Lisbon, with Sintra taking the top spot. I love them both for different reasons.

If you’re looking for that Instagrammable fairy tale location with intricate palaces and stunning vistas, then hop a train and take the 40 minute ride into Sintra. Alternatively, many tours also run from Lisbon, which the added bonus of stops in Cascais and Cabo da Roca. The highlight monuments in Sintra are Palacio da Pena (book your tickets online), Quinta da Regaleira, Palacio de Monserrate and Castelo dos Mouros.

If a charming medieval village is more your speed, then board the train to Óbidos. The village’s intimate size is perfect for a more relaxed, leisure exploration through cobblestone streets, quaint shops and delicious restaurants. Be sure to taste the ginja, a traditional sweet cherry liqueur.

Once a small fishing village, Belém grew in importance and popularity in the 16th century when it became the port of departure for Portuguese explorers. The Jerónimos Monastery was built to commemorate the return of Vasco da Gama from India and is now one of the most visited monuments in Lisbon.

While the long queues can be intimidating, I’d say the monastery is worth visiting at least once. And to be honest, due to the large size of the grounds, it won’t feel quite so packed inside. Be sure to pop across the street to visit Belém Tower and Monument to the Discoveries. Cap off your day with a sunset and wine cruise on the Tejo River as you say goodbye to Lisbon.