The D&O Diary is on assignment in Europe this week, with the first stop along the way in the beautiful, historic and sun-drenched city of Lisbon, or as the natives say, Lisboa.

Lisbon is the westernmost capital city in Europe, with a population of about 550,000 in the city proper, and a total of around 3 million in the sprawling urban area. History is layered deep in Lisbon. Rising above the city in the Alfama district is the Castelo de São Jorge (pictured left), originally a Visigoth fortification, later held by the Moors until they were thrown out of Portugal in 1147. The castle ramparts provide a scenic overview of the central city and of the Tagus River (pictured below), or the Rio Tejo as the locals call it. Down below to the South of the castelo is the Baixa District, beautifully built in a rigid grid system after the Great Lisbon Earthquake of 1755. Beyond that are the narrow streets of the Bairro Alto climbing to the top of another of Lisbon’s steep hills.

Although with a little vigorous walking you can cover the city center on foot, a more pleasant way to see the sights is to board one of the venerable street cars (electricos). The no. 28 street car (pictured below) provides a particularly fascinating ride as it takes you past many of the city’s most historic sights. There is, of course,  a certain intimidation factor in taking public transportation in a foreign country – first there is the confusion about what the fare is and how to pay it, and then there is the nagging anxiety that perhaps you are on the wrong train or going in the wrong direction. The first time I boarded the no. 28 street car, after having fumbled through the process of paying my fare, I decided just to ride the journey out, to see the entire route. The line terminated, appropriately enough at a cemetery. It is where the journey ends for all of us.

Many of the words in Portuguese are similar to Spanish, but overall the two languages sound very different. The letter “s” is pronounced with an –zh sound or a  –sh sound, and many of the vowels are rounded and spoken far back in the throat. I think if you closed your eyes and just listened to the language, you might think you were hearing a Russian speaking Italian. I memorized a few phrases, the most useful of which was não falo Português (I don’t speak Portuguese)  — which ,for some reason, always drew a laugh, perhaps for the irony of using language to say I don’t speak it. I also came equipped with my one indispensable travel phrase, which in Portugal is said as uma cerveja, por favor. After returning from my not entirely planned visit to the cemetery, I found a sidewalk café on a overlook in the Bairro Alto (the last picture at the bottom of the post, just before the video) where I successfully deployed my one indispensable phrase. I finished the café transaction with the delightfully ornate word in Portuguese for “thank you” – obrigado, which is pronounced with a powerful Iberian trilling of the letter “r.”

Feeling a little bolder about public transportation the next day, I took a tram out to Belém, where the Tagus meets the ocean. Many of Portugal’s famous voyages of discovery set sail from there. The huge Mosterio des Jerònimos was built by Manuel I to give thanks for Vasco de Gama’s safe return from India. The Torre de Belém, built in the early 16th century, sits along the river and affords views out to the great ocean beyond. It is quite something to consider that for a brief time five centuries ago, tiny Portugal (about the geographic size of South Carolina) bestrode the globe as the preeminent maritime power. The moment was short-lived, as the difficulty and cost of defending its mercantile advantages proved too great to maintain, particularly as the country dealt with problems and distractions closer to home. The legacy of the colonial era lives on in Lisbon, in the faces of residents from places like Brazil, Mozambique and Macau.

If Lisbon is figuratively layered in history, it is literally paved in small cobblestones, called calçadas. Many of the walkways are decorated in ornate patters of alternating black and white stones. Hiking around on cobblestone walkways can wear out your feet pretty quickly, but I really came to admire and appreciate the sheer artistry of the elaborate stone patterns. In his book of essays about Lisbon entitled “The Moon, Come Down to Earth,” American writer Philip Graham, who was also fascinated with the cobblestones, describes the experience of taking up a loose calçada in his hand: “I twist and turn it in my hand and feel the attentive craft, how each of the stone’s six sides has been carefully chipped to a rough approximation of a smooth surface. That must be why I feel such affection for these stones – they’re as individual as people. But it’s an affection laced with sadness, because so much of their originality –their five other sides – is normally buried out of sight. And that’s a lot like people, too.”

This innate sadness is something of a theme. One of my main motivations for choosing to go to Portugal was a desire to hear the famous traditional music, called fado. Lisbon is to fado as New Orleans is to jazz. The word “fado” means fate, and the music is infused with mournful sadness. The lyrics convey a spirit of longing and regret, embodied in the Portuguese word saudade. Fado has undergone something of a revival recently, spurred by the popularity of stars such as Mariza (through whose songs I first encountered fado).

I spent a fair amount of time trudging around the narrow streets of the Bairro Alto looking for just the right fado club. I wound up choosing one because it seemed the least touristy, but my instincts proved faulty. Soon after I ordered my dinner,  a tour bus full of Japanese tourists filled the place. Fortunately, the music did not disappoint. The fadista, who was heartbreakingly beautiful as well as talented, was accompanied by a mandolin and a guitar. Although I couldn’t understand the words, her singing conveyed the sorrowful message of the lyrics. (Oddly, many of the songs seemed to be about Lisbon. The chorus of one song was simply “Leezh-bo-ah, Oh!, Leezh-boh-ah.”) It was a great show, even though the Japanese tourists insisted on standing up and taking flash pictures – repeatedly – throughout  the performance.

On my way out of the club, I said to the singer “Amo sua música” (I love your music) to which she responded by saying (in Engish) “In that case, you’ll want to buy one of my CDs.” I laughed and said to her “Quanto é?” (How much is it?), to which she responded (in English) “A bargain at fifteen euros.” I handed her the money, she handed me a CD, and I said to her (in English) “Thank you. Goodbye,” to which she responded by saying “Obrigada. Adeus, meu amigo.”

After I left the fado club, I meant to go back to the hotel. It was late and I was tired. However, on my way  to the hotel, I was drawn by the irresistible sound of Brazilian music. I wound up going into a samba club and standing at the crowded bar. I have always thought of samba music as a cliché, but this was something different. I would say that the place was rocking, but that is not quite right –the place was swaying. It is impossible to listen to samba music and stay still. Everyone’s head was bobbing along to the beat. One impossibly tall young woman (whom I later learned was the bass player’s girlfriend) was walking around the club and drawing random people into dancing. She found it particularly amusing when she tried to dance with me. I am sure part of the amusement was that I was easily thirty years older than everyone else in the place, and I was certainly the only one wearing a blazer and a button-down shirt. Her laugh seemed to say “Look, I got Pops here to dance! What’s this guy doing in this club, anyway?” I survived the samba dance lesson, but I did stay out a lot later than I had intended.

The next morning (a little later than I had hoped), I took a train from the Rossio Station is Lisbon to Sintra, in the mountains about 45 minutes away. Sintra – prounced SEEN-tra, with more of that lovely trilling of the “r” — is the site of several former royal palaces and castles. It sounded pretty interesting from the guidebooks, but what the guidebooks didn’t manage to convey is that it would be crime to visit Portugal and to miss Sintra. The Palacio Nacional de Sintra (pictured to the left) is stunning; even on the warm afternoon that I visited, the beautifully tiled rooms were cool and comfortable. But the best part of visiting Sintra is the Castelo dos Mouros, located about 1,500 ft. above the town on a small mountain. The Castelo, which can only be reached (as far as I can tell) by a very vigorous hike up a steep, rocky incline, was built in the 8th or 9th century by the Moors, later captured by Norse invaders, and ultimately taken by the Portuguese. I arrived at the mountain top drenched in sweat, but the exertion was well worth the effort. The views from the vertiginous battlements were absolutely astonishing. I stayed up there for a couple of hours, exploring the castle walls and admiring the incomparable views.

As I headed back to Lisbon on the train, I was certain that I had done something truly special that day. I also started to understand why the traditional Portuguese music is so mournful. The country is beautiful and has a proud and rich history. Yet its greatest moments were centuries ago. Little of its literature is translated into other languages. Its wonderful and distinctive wine and music are little appreciated outside of the country. The country spent the better part of the 20th century suffering under a repressive dictatorship. Its beautiful capital city is often overlooked in favor of more glamorous places like Paris or Rome. When I told the cab driver back home who took me to the airport that I was going to Portugal, he said “Portugal? Where is that exactly?” (Admit it, when you first saw that this post was about Lisbon, you said to yourself, “Lisbon? Why did he go to Lisbon?”)

Friends, I am here to tell you, Lisbon is a great place. It is a shame that the city is often overlooked. If you have ever sampled a glass of Portuguese vinho tinto and observed to yourself with surprise and delight, “Hey this stuff is really good!” then you know what it would be like to visit Lisbon.

More Pictures of Lisbon:

The Alfama, the city’s oldest district

The Baixa District

Praca Do Comercio

Castelo dos Mouros, in Sintra

Bela Lisboa

Wonder what fado sounds like? Here is a bonus video — this is Mariza peforming a fado concert at the Torre de Belem: