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Exploring Abroad: Portugal's Fairy-tale Castles and Villages

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.

Portugal is all about its connection to the sea, so the fish we ordered for lunch was superbly prepared.

Ginjinha is a popular sweet cherry liqueur often served in tiny cups made of chocolate.

Lots of spots in town serve it, but our guide from a walking tour in Lisbon tipped us off to THE place to go for the best recipe.

Óbidos was an absolutely delightful day trip destination. We’re so happy we got to experience it during our visit to Portugal! 💖

Another “must do” excursion from Lisbon is the magical town of Sintra. Dotted through the hilly forests are gorgeous palaces, exquisite villas, and the ruins of a 10th century Moorish castle.

Our first stop was the Castle. From its perch atop a rocky peak, it once guarded the entire region. Walking along the steep, curving walls was extremely strenuous.

On an opposing hill sits one of Europe’s most magnificent palaces, Palácio da Pena. Restored to its former grandeur from the time when Portuguese nobility escaped the revolution in 1910 by fleeing to Brazil, this beauty attracts millions of visitors each year.

The exterior is a mix of several architectural styles with vividly painted walls.

“Over-the-top” is the best way to describe the lavishly decorated rooms.

Touring these two properties took a lot of energy, but since this was our only day to visit Sintra we pushed on to a third stop, the Quinta da Regaleira.

Although the neo-Gothic villa is itself a show stopper, the mansion’s expansive gardens are the main attraction here.

Specifically, an odd feature called “The Initiation Well.” A spiral staircase descends to a tile floor depicting a cross symbol from the Knights Templar.

From there visitors follow a long tunnel with mysterious openings along the way.

Until you suddenly emerge back in the gardens. What does it all mean? Nobody really knows, but this UNESCO site was a heck of a way to end our fabulous adventure in Sintra!

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