Lisbon was going to be a month. It became three. Then we still felt like we were leaving too early.
We had a view of a castle right outside our apartment window. That will spoil you for other windows for a very long time.
Finding a long-stay apartment in Lisbon’s Chiado
We stayed in Chiado, one of Lisbon’s most elegant neighborhoods and the historic center where Fernando Pessoa hung out at A Brasileira. Castle-view included: São Jorge Castle sits on the hill just to the northeast and dominates the skyline. Portugal taught us a new appreciation for mosaic tile, which they’ve truly mastered. And azulejo tiles from the 1920s in a Lisbon apartment hit different from ceramic tiles anywhere else.
Living in Chiado, Lisbon
Chiado is where old and new Lisbon meet. Bookstores, cafés, theaters, and the kind of narrow streets that funnel you toward miradouros with views that stop you mid-sentence. Fado bars where the singing spills into the alley. A grocery store the size of a walk-in closet. Everything walkable, though Lisbon’s hills will remind you what your calves are for.
The Duque da Rua fado spot introduced us to soulful sounds we’d never heard live before. Green wine (vinho verde) became a discovery. Pastel de nata became a food group.
A typical day in Lisbon
Coffee at the same pastelaria every morning. Groceries at the corner market. Long afternoons at a co-working spot. Sunset at a miradouro with a small bottle of wine and no plans. Dinner was often a bica and a pastel de nata standing at a counter, or grilled sardines at a hole-in-the-wall taberna where the menu was on a chalkboard.
Weekends we hit Sintra, which has more beauty and historical feats of architecture than any small town has ever deserved. Pena Palace looked like what happens when you give a castle builder crayons. The Castle of the Moors was the unconquerable fortress from every medieval tale. Quinta da Regaleira was an unexpected wonder.
We also spent New Year’s Eve in Madeira, which the Guinness Book of World Records has recognized for its fireworks display. We watched from a catamaran in the harbor. The tropical scenery was beyond what we’d imagined. And the carros de cesto (a wicker sled with no brakes down a steep hill) was foolish and dangerous. We liked it so much we did it three times.
Lisbon: our verdict after 3 months of living there
Lisbon rewards people who slow down. Three days here and you get the highlight reel. Three months and you get the actual city.
We haven’t been back yet. We keep saying we will. Lisbon is a city we left unfinished on purpose.
Lisbon long-stay stats
- Duration: Three months, winter into spring
- Neighborhood: Chiado
- Cost tier: Mid-range
- Walkability: Excellent, if you like hills
- Wifi: Fast in most apartments
- Cat-friendly: Yes
- Best for: Long stays, romantics, remote workers who don’t mind stairs, wicker sled thrill-seekers
- Would return: Yes, and we still owe ourselves the trip
Book the stay: Our Chiado apartment on Airbnb →
