Construction of a walled village began in the eighth century on a hill about 80 kilometers to the north of Lisbon. Originally a Moorish town, it was captured by the Portuguese and its wall and castle underwent significant renovation. Although the 1755 earthquake caused significant damage, the wall, castle and medieval streets still exist.

Unfortunately, our visit coincided with the annual Medieval Market, two weeks in which the town transforms into a festival with medieval costumes and customs everywhere. While that sounds like fun, and to some extent it is, it also makes the town feel a bit like a Disneyland attraction, teeming with tourists (both Portuguese and foreign) crowding almost everything. It’s a good thing for the town, bringing money into an area that doesn’t have much beyond agriculture and tourism.

The hilltop location means terrific views of the pastoral valleys that surround Óbidos, with farms popping up beyond the rooftops. There’s vineyards and undoubtably olive trees.

The castle is impressive, with towers and a walkway across the top that is populated with visitors. Although well-preserved, there are places, especially the steps up and down, that feel less than secure.

What does keep Óbidos from going full-on DIsneyland are the occasional views of the castle intermingling with the lives of the residents. As with everywhere in Portugal, including the heart of the cities, laundry is hung outside as dryers are rare. What an amazing experience to go outside to hang up the laundry in front of a castle dating back 1000 years!

Another intersection of the current and the past shows up in the graffiti. Graffiti and wall art are everywhere in Portugal, typically some real art mixed in with traditional tagging. In Óbidos, it’s a big different. The city is mostly white with blue accents. Virtually all of the graffiti is, as if dictated by law, blue. It’s often handprints, for some reason, which are devoid of the modern signs of typical tagging, somehow enhancing the medieval feeling.

And then there was the festival. While we didn’t stay for the Market, as it’s an evening event and we had to catch a bus back to Lisbon, some of the characters were in place towards the end of our visit.

Almada is just across the Tagus River from Lisbon. It’s accessible by ferry, bus, train, and car, the last three quite simple by crossing the Ponte 25 de Abril, also known as Lisbon’s Golden Gate Bridge. It’s a large suburban area with several urban and village centers, beaches, and a fishing area.

Taking the ferry from Lisbon’s Cais de Sodré to Cacilhas lands visitors at a seaside area that has some restaurants and a dockside area with people fishing. It also has a beautifully run-down set of buildings along the water. They’re all falling down and going inside would require a hard hat as they seem to decay regularly.

There are two directions to go form the Cacilhas ferry terminal. One is towards the bridge and offers a terrific view of Lisbon from a glass elevator that goes up the rock face. The other direction is into the city of Almada. Almada isn’t known for historical landmarks in general, but does have some excellent restaurants, a nice church (what city or village in Portugal doesn’t have a church?), and a relaxed feeling.

Not that far from the center of town is an area known as Romeira. Romeira features decaying industrial buildings, including some spectacular towers that once held flour, some of the best street art in Lisbon, and a small number of people living in makeshift homes. There’s traffic through it but not many people walking, giving it a somewhat edgy feel. It’s a photographer’s paradise.

Some of the best street art here is by well-known artist Styler.

Another ferry goes from the Belém district of Lisbon to Trafaria, a bit west of Cacilhas. Trafaria greets visitors with a small beach with boats haphazardly strewn across the beach and moored in the water. Looming over the beach is more industry, dominating much of the landscape.

The village by the water is typical of Portugal, with narrow streets and alleys lined with small houses, and restaurants that grill sardines outside. Some structures, especially the industrial ones, are decaying, like in so many other places with dead industries. The only signs of life in these buildings are feral cats and kittens.

Old buildings including forts can be found around Trafalgar. The structures closest to the water are fenced off and the ones inland are difficult to access. Those are being saved for a return trip, along with a visit to a long-closed water park, once local assistance is enlisted.

Thanks to Anabela Melo de Carvalho for information about Almada.

The Douro River starts in Spain and ends in Porto, where it meets the Atlantic Ocean. It is best known for its vineyards and wine making, and particularly for its central role in the making of Port wine. The valley is spectacular, with steep hills covered in terraced grape vines, beautiful bridges, and winemaking estates and homes.

Our visit began at the Santa Apolónia train station in Lisbon. The ride to Porto is about three hours and the trains are quite comfortable, even in “tourist class.” Arriving in Porto, there is a transfer to the train going to Regúa, a prominent town that takes another two hours on the train. This train, while not as comfortable, often offers views of the river and the south slope vineyards. It’s an old line, often single-tracked which occasionally causes delays while waiting for an oncoming train to get through.

Regúa embraces today’s Portugal, with a well-preserved quaint “downtown” and tasteful modern buildings behind the downtown. As it sits on the river, there are docks and riverside bars. As with every town and city we’ve visited, there are some attractively abandoned buildings.

The plan was to take a six hour cruise on the river. Given the heat (34C at the peak), it’s a blessing that this fell through due to dam repairs. Instead, we ended up with another train ride, this time farther up the Douro to Pinhão, a village smaller than Regúa and the departure point for a lot of boat rides. We took a smaller boat for a much shorter ride, a pleasant afternoon jaunt on the river. The tour started out with a group of drunk Americans yelling about tequila (apparently they were confused about what country they were in) but fortunately, they moved to an upper deck and everyone else was happy.

Back to Regús and out the next morning to a winery. We would have liked to visit a smaller winery with a chance to speak with winemakers or vineyard managers but it was too difficult to arrange, especially as we didn’t have a car. We ended up with a group at a large winery. We had a tour and tasted some decent if unexceptional wines, but it turned out the group, which was mostly Americans with a few people from China, was a lot more interesting than the drunk Americans on the boat ride.

After the winery, we headed back to Porto. Porto is Portugal’s second largest city, much smaller than Lisbon, but with lots of character. Although inundated with tourists like Lisbon, the city center is much smaller so you can escape more quickly. We found a funicular that was fun to ride for all 90 seconds it took to go up a hill at a 75 degree angle.

Porto stands in contrast to the rest of the Douro Valley, it’s urban and modern and busy. We didn’t explore the port houses on this trip but did enjoy the views of the city. It was extremely hot and we ended up in a park the afternoon before we left. Walking through  the park, we encountered a museum – Museu Romântico da Quinta da Macieirinha – that had served as the home of the exiled King of Sardinia in the early 19th century. The museum is not on the path most tourists take so it was quite empty. Well-preserved in a condition close to original, it was quiet and enjoyable, the last stop on the trip north.