Spending weeks scouting a potential expat destination gives you time to immerse yourself in the local culture at a relaxed pace. To wander through neighborhoods and savor the cuisine. Enjoy the attractions. And to venture out into the surrounding area for enriching day trips.

From Lisbon we first explored the medieval town of Óbidos. Originally a Roman settlement, the location was next occupied by the Moors before being retaken by the Portuguese in 1148.

Given to Queen Isabel on her wedding day in 1282, Óbidos has since been known as the “town of the Queens.”

Strolling through the narrow, cobbled streets was eerily like being transported back in time.

At the highest point of Óbidos stands an impressive castle surrounded by fortification walls.

Walking around up there was honestly a little scary (no handrails!), but the expansive views demonstrated why this site was originally chosen. Nobody was going to sneak up on you, that’s for sure....

Cynthia:  We’ve been wanting to visit this popular expat destination for some time. Sorry to report our trip to explore Lisbon got off to a rocky start. I don’t know what was going on at the airport, but the crowd waiting to get through immigration was massive.

Edd:  It took us a couple of hours there. When we got to the city we couldn’t find the Airbnb rental and were clickety-clacking our suitcases up steep hills over Lisbon’s tile sidewalks.

C:  After a red-eye flight from the States we were beyond exhausted when we finally arrived at the apartment.

E:  Our place was in a hip area called Barrio Alto. This was the view from the terrace.

C:  “Hip” means the bars and restaurants spilled out onto the streets, and patrons were eating and drinking until the wee hours. That, plus major jet lag, made the first few nights less than restful.

E:  We’re sharing this not to complain, but to make readers aware the...