Editor’s note: during my month in Lisbon, I visited Sintra (read about it here), but did not make it to Obidos or Evora. We are fortunate to have Sam Spector to fill in those gaps for us, as well as offer his insights on Sintra itself. For more of Sam’s writing, click here to visit his index page.

In my third article on Portugal, my newfound European dreamland, I want to tell you about three incredible cities outside of Lisbon. The first and most popular place to visit outside of Lisbon is actually a suburb that you can get to easily by Uber or train, which is the city of Sintra. Sintra is one of the most regal cities in Europe with several palaces and castles. The streets are narrow with limited parking, and it is packed with tourists, so you are better to take a tuktuk, Uber, or the bus from the train station rather than to drive your own car in this town. The first stop you should make upon arrival to Sintra is its most famous site, the Pena Palace. This brightly colored palace that has towers of bright red and yellow was built in the mid-19th century as a royal summer palace and combines many eclectic architectural styles from neo-Manueline, neo-Islamic, neo-Gothic, and neo-Renaissance. With drawbridges, picturesque views, lush gardens, and tall clock towers, Pena Palace looks like something out of a fairytale and is listed as both a UNESCO World Heritage Site and one of the Seven Wonders of Portugal. Alongside Lisbon’s Belem Tower, it is likely the nation’s most iconic site. I suggest you arrive early though, as the line to get inside and view the rooms of the palace can be several hours long.

Pena Palace

Another well-known destination in Sintra is the nearby Castle of the Moors, a ten-minute walk through a forest from the Pena Palace. Less of a castle and more of a set of fortified walls alongside a mountain, the Castle of the Moors provides spectacular views of the valley and city of Sintra below, and also of the Pena Palace, which overlooks it from above. As the name implies, the medieval castle was built by the Moors in the 8th and 9th centuries in their takeover of the Iberian Peninsula.

The Castle of the Moors

My favorite place in Sintra was the Quinta da Regaleira. This sprawling property with its own palace and many structures was built at the end of the 19th century by an eccentric wealthy man and is essentially the Portuguese version of Hearst Castle. The must-see spots at this over-the-top property are its Catholic chapel with frescoes and carved statues, fountains, the underground tunnels, a grotto which leads to a pond and waterfall, and the towers. Yet, the most impressive and famous tower is the one known as the Initiation Well, which is an inverted tower, meaning that it is a tower that goes below ground instead of above ground, with a spiral staircase that goes down approximately 90 feet. It is one of those things you have to see to truly believe and that will be a fascinating, seemingly mythical experience that you will not find anywhere else. The Initiation Well and the tunnels below were inspired by Tarot mysticism.

The Initiation Well

There are many other sites to visit in Sintra, and one would need several days to do them all; some of the most noteworthy are the NewsMuseum, Park and Palace of Montserrate, Convento dos Capuchos, the Sintra National History Museum, and the 16th century National Palace with its two famous humongous conical chimneys. With Sintra so close to Cascais, which I wrote about in my Lisbon article, many people will do a whole week of just these two cities and never have a dull moment.

An hour or so north of Sintra by car is one of Europe’s most romantic cities, the walled city of Obidos. As you approach Obidos, you will go up a giant hill with a medieval castle from the 12th century. This castle is another of the Seven Wonders of Portugal. When driving up to the city, my wife looked in awe at the castle and asked if we would have a good view of the castle from our hotel. I told her not exactly. When she looked disappointed, I explained to her that that was because the castle was our hotel! An essential Portuguese rural experience is staying in what is called a pousada. Pousadas might be former castles, monasteries, or convents that have been turned into private hotels. Some can be a bit pricy; ours was $250 per night, which is more than I usually spend on a hotel, but a bargain for the experience of getting to feel like royalty for a night in a medieval European castle. The old city of Obidos is completely walled in and it is worth climbing up the wall from next to the castle at either sunset or in the morning and walking the entire length of the wall and looking down into the town below. Looking away from the town, not only will you see beautiful valleys, but you will also spot Roman walls and aqueducts surrounding the town. In doing so, you will see right into people’s kitchens at some points, notice trees with colorful fruit, and look down at tiled roofs and the maze of cobblestone streets. While there are no major tourist attractions beyond the castle in Obidos, walking through the town and exploring the shops and taking in the atmosphere of the town of 3000 people will be a highlight of a trip to Portugal. Make sure while in Portugal that you stop and take a shot of ginja; there are many kiosks and shops selling them throughout the country. Ginja is a sweet cherry liquor that is served in a dark chocolate little cup, and after drinking the shot, you eat the cup it comes in as an added bonus. Of anywhere in Portugal, Obidos is the best known town for having this treat.

The castle at Obidos – and my hotel!

For the final town in this article that you should visit, go two hours east of Lisbon to the town of Evora. Evora is in the region of Alentejo, which means “Beyond the Tagus River” and takes great pride in its identity of being an agricultural area that looks like the Tuscany of Portugal. The entire town is a UNESCO World Heritage Site, and the combination of its ancient attractions coupled with its young, vibrant population as a college town gives Evora a great vibe. In the center of town is a 49-foot tall, 82-foot wide Roman temple called Templo de Diana, erroneously named after the Roman goddess of the moon, when it was actually built in the 1st century for Augustus Caesar. At night the temple is lit up, and its imposing structure leaves an impression on any visitors. Near the temple are a couple other important attractions, including the 16th century Graca Church and the large Manueline-style Evora Cathedral. The Evora Cathedral is the most famous city cathedral in the nation after Lisbon’s; it is well worth a visit except that when I went there I had reached that inevitable part of any European trip where I was “churched-out” and they all started to blend together.

The Temple of Diana

However, one church in town where I did not experience church fatigue was the Chapel of Bones in the Church of St. Francis. This small chapel was built in the mid-19th century by Franciscan monks who exhumed 5000 corpses and completely decorated the inside of the chapel with tens of thousands of skulls and bones. It is an incredible, bizarre, and haunting spectacle that might not be for the faint of heart, but will captivate most visitors. You can also read the various poems displayed throughout the chapel.

A wall in the Chapel of the Bones

Finally, another fascinating site in the middle of the city (not far from the Roman temple) is the Rua do Cano, which is home to the city’s Roman aqueduct. However, this aqueduct is unlike any that I have seen. While the city was building up, they did not want to destroy the aqueduct, but at the same time, they needed that space, so what did they do? They built homes and shops into the archways of the aqueducts! Imagine that being your house! End your day or two in Evora by going to the Giraldo Square, which will be filled with excited college students, and hop into one of the many festive bars and restaurants surrounding the square, which provide great food at reasonable prices and are open late to fit the clientele of the young Evora residents.

Rua do Cano

These three towns are each remarkable in their own way and would enhance any trip to Portugal. While Sintra has been overrun by tourists, you will see that it is for good reason as its attractions are worth crossing the world to see. In Evora and Obidos, you will find charm and a touch of real Portugal that will be so refreshing and so beautiful, and you will see why many who visit Portugal decide to not go back where they came from.

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