After four wonderful days exploring Madrid, I boarded an overnight train to Lisbon, eager to get to the city I fell in love with from a travel show. Arriving in Portugal, I was tired but energized, anxious to soak up another new location and culture for four days before heading back to Madrid and then back to the states.

Day One

My train pulled into Lisbon at just around 8a on Sunday morning, and I emerged from the train station to a city unlike anything I anticipated. From the first few moments, walking out into a massive traffic circle with a statue at the center surrounded by generations-old buildings, I knew I was in for a treat. The city is really old, with Romans tracked to the Iberian Peninsula as early as 202 BC (yes, you read that right); centuries of history are evident in every detail of the architecture, around every cobblestone street corner.

I had a few hours before I could get into the studio I’d booked for my stay, but thankfully the host pointed me to a nearby metro station with luggage lockers, so off I went across another amazing plaza to drop them off. The city was clearly still asleep at this early hour; the fountain in the plaza wasn’t running yet and there was hardly anyone else out and about. Which was fine by me—it was like my own private introduction to Lisbon.

Bags secured, I went in search of caffeine. It didn’t take long to realize that the only place really open for business at that hour was the favorite known around the world, Starbucks. I did not hesitate to order an Americano and breakfast sandwich to get my day started, my one indulgence into chain comfort food during the trip! And it was well worth it, as I perked up enough to head out for some initial sightseeing as I got my bearings around the city center. I’d heard that Lisbon is a city of hills, and I learned quickly just how true that was, hiking uphill to get a better view of the landscape. I found my way to one of the handful of city elevators and climbed up as high as my fear of heights would let me go; I might not have made it all the way to the top, but the view was still incredible. 

From there, I went downhill towards the water. Lisbon is set on an inlet (I don’t know if that’s the correct geographical term, but let’s go with it) where the Tagus River meets the Atlantic Ocean, so when you’re at the water’s edge, you’re actually looking at more of Portugal across the way. Heading down Rua Augusta, a main drag with shops and buskers and tourists galore, you walk through this massive archway and into a wide open plaza surrounded on three sides by sprawling buildings and water on the fourth. I walked the whole length of it until I was right at the coastline, where there’s just enough room to sit and watch the city. Which is exactly what I did.

On my way back to get my bags, it was time to really get my Lisbon experience started: I headed directly to Manteigaria, home of some of the best pasteis de nata in all of Portugal. What’s pasteis (say: past-AISH), you ask? Only the most magical sweet pastry you’ll ever have the privilege of enjoying if you’re lucky enough to find yourself in Lisbon, that’s all. Seriously. I was expecting these egg custard and flaky pastry cups to be wonderful, but nothing could’ve prepared me for that first bite: warm and buttery, creamy and sweet…seriously incredible. And at just a euro each, I knew there’d be plenty more in my future.

Finally, I grabbed my bags and made my way to the tiny studio I’d call home for the next few days. If I’d change one thing about my trip, it’d be the lodging. The studio worked really well, and at just about $150 total for my four night stay, it’s certainly an unbeatable deal. And yet, I think next time I’d splurge an extra $30/night or so for a nicer spot. That said, I made myself at home (once I lugged my bags up another major hill!) in no time—I hopped in the shower and freshened up enough to head out for one good meal and some more sightseeing.

I found myself at the Time Out Market, a spot that’s the perfect introduction to Lisboan cuisine: dozens of the city’s best restaurants under one roof and ready for exploring. I settled on chef Marlene Vieira‘s menu (the only female chef in the Market!) and indulged in an amazing Portugese-style roast beef dinner. After dinner, I wandered the area a bit and soaked up the gorgeous evening; I watched kids play in a part nearby (in a not creepy way!), I walked along the coastline for a bit, and then still not ready to head in for the evening, I stopped at another plaza I stumbled into and decided to treat myself to a port wine flight. I chatted with the women at the table next to me for a bit and even asked them to take a photo of me, doing my best to just give in to the lovely moment. As I headed back to the apartment for the evening, I stopped for one more pastel for good measure.

Day Two

I spent Sunday evening trying to make plans for Monday, which proved more difficult than I expected; apparently everything, from attractions to restaurants and more, are closed on Mondays in Lisbon! I had a whole list of restaurants I wanted to try, of sights I wanted to see, and I kept coming across closed hours—so frustrating. 

Eventually, I got my day sorted and decided to jump on the tram out of central Lisbon to check out Belém, an area just west of downtown Lisbon with amazing views of the water and the city. Plus, it’s the home of Pasteis de Belém, known not only as the best pasteis out there, but the original home of them, too. I took mine to go, but not before wandering the space: counter service with a line around the block, a sprawling cafe area complete with patio, and a glass-walled kitchen where you can watch the magic happen. 

With pasteis in hand, I walked towards Jerónimos Monastery, a church and monastery with origins dating back to 1495. Closed on Monday (of course!), all I could do was take in the gothic details and sheer size of the massive buildings. From there, I walked along the water to a few more monuments in the area (including Padrão dos Descobrimentos, built for all the journeys of discovery that originated from Portugal) and settled in a local spot for a late lunch of prawns and chips while I let the rain that had moved in pass by. Just down the way from there, I found the Torre de Belém, an outlook and security post build in 1519. Also closed on Mondays, all I could do was check it out from all angles and picture a Game of Thrones scene unfolding inside.

Since I couldn’t go into any of the UNESCO World Heritage Sites (ugh), I made my way back to Lisbon and decided to join the throngs of tourists waiting for a ride on Tram 28. Lisbon has a pretty decent public transit system, including a metro, buses and several tram lines. Tram 28, however, has become a go-to for visitors, as it winds its way through narrow streets of downtown Lisbon and uphill to some of the city’s best look-out spots. I had to wait about an hour (!) to get on, but with no real agenda for my day, I was fine to give over that much time to the adventure of it all. It paid off when I got a window seat to enjoy as the shops, restaurants and pedestrians zipped by.

I got off the tram at Miradouro das Portas do Sol, a look out with some of the most breathtaking views of the city. One thing I’d read before I got there was that Lisbon is dotted with these “miradouros” (per Google translate, “gazebos” but really, look-outs or photo spots), and that it’d never be a bad idea to stop when you see one. This, my friends, is true. From Portas do Sol, one can see the sprawling rooftops of a city built centuries ago, with castles and cathedrals looking down on it all. The tram had brought me to the top of the Alfama district, a winding, cozy neighborhood east of the city center known as the birthplace of fado, Portugal’s signature musical style. The narrow, curving streets are lined with restaurants that look like nothing more than holes in the wall, until you enter and the space fans out into a dining room and a small stage where the fado musicians perform. I was in the neighborhood a bit too early for the evening’s performances, so instead I grabbed a table at a cafe on the plaza and wrote out a few postcards while I watched the city settle into a lovely spring evening.

Day Three

Every time someone heard I was going to Lisbon, their first suggestion was to be sure to leave that city and head out to Sintra, a town just northwest on the edge of a national park. So of course, I found a way to fit that day trip into my plans, heading out on an early-ish train first thing Tuesday morning; as if built for tourists (maybe it was!), there’s a train that starts in Lisbon and ends in Sintra, just 45 minutes from point to point. 

The town of Sintra is small but welcoming; locals seem to have embraced the fact that they’re a go to, and have put in place all kinds of services to capitalize on the business, from taxi services to public bus services, restaurants and shops. I didn’t spend much time in town, as I was set on getting to the real attractions of the area: the castles and palaces! The proximity to the ocean, the protection of the mountains and the generally lush surroundings made the area perfect for royal retreats, military defenses and more. On my day trip out, I hit the two main spots: the Castelo dos Mouros (Castle of the Moors) and Pena Palace, each accessible via the public bus loop that picks tourists up from the train station and shuttles them from one site to the next. 

Though my fear of heights threatened to derail my exploration of the Castle of the Moors, I did my best to keep focused and climbed up to a few great views from the turrets of this 8th century structure. I’m fairly certain it’s the oldest building I’ve ever visited, and it’s in fine shape for being over a thousand years old and visited by thousands of tourists a day. Pena Palace doesn’t have quite as deep a history, completed in 1854, but what it lacks in heritage it more than makes up for in personality. Converted from a convent, it was created as a royal getaway and was intentionally built in vibrant colors with fairytale flare.

I didn’t have a ton of time on this part of the adventure, because I needed to get back to Lisbon for my evening dinner tour. On my first morning in town, I saw a topless SUV outside of Starbucks emblazoned with “We Hate Tourism” on the side. So of course I googled it, only to discover the most bad ass tour company out there. The site touts their deep pride for their city and a sort of resignation to the booming tourism industry; in a “if you can’t beat ’em, join ’em” kind of way, the team apparently decided to craft tours their own way, and has been marching to the beat of their own drum ever since.

I decided to fill my last evening with their Dinner With Us (Or Starve) adventure, and the evening did not disappoint. A ball of energy named Marco pulled up to meet us—just me and a young couple from Boston—and quickly whisked us away to Lucimar, a truly local spot in the Campolide neighborhood north of the city center. All we had to do was sit down, and before we could so much as put our napkins in our laps, the food started arriving like magic. A carafe of vinho verde; three different kinds of bread; pork and seafood and eggs and on and on and on. We ate like animals, as Marco promised we would, before we were back in the van and I found myself back at Pasteis de Belém for dessert. Only this time, it was dark out and we got to enjoy Belém Tower all lit up as we enjoyed the sweet treat. As a last stop, Marco drove us up to Palácio da Ajuda, a spot I hadn’t come across in any of my research but as breathtaking as any other palace in the city. We sipped on port and snapped a few last pictures before our magical night in Lisbon wound down for good.

Day Four

As I was living it, I often felt like I wasn’t doing enough to soak up all that Lisbon, truly one of the most incredible places I’ve ever visited, has to offer. Between the lingering sinus infection I was fighting and generally being bad at motivating myself to get moving, it was hard not to beat myself up for not doing more. But now, as I recount all my adventures in just four days, I realize just how much I really did!

By my last day, I was pretty exhausted and knew I didn’t have enough time to do more sightseeing and pack and get to the airport in time for my flight back to Madrid. I summoned enough energy to head out for some final souvenir shopping nearby, but otherwise I devoted most of my morning to the jigsaw puzzle that was repacking my bags with all the new swag I’d acquired over the last week. I managed it successfully (but just!), then loaded it all up to get to the airport. 

As I waited for my economy flight back to Spain, I could’ve fit in some journaling or read the book I’d bought back at O’Hare, but instead I just watched the world around me go by. I think subconsciously I was soaking it all in, letting the last several days settle into my memory and add their influence to my world view. I landed back in Madrid around 5p, where I picked up the shuttle to the nearby hotel I’d booked for my very last night. After a good dinner out, I picked up a bottle of white and indulged in a luxuriously long bath to rest my bones for the long flight home the next day.

If you’re thinking about a trip to Lisbon, I have just one word for you: go. Sign up for Flyglitch, wait for a great deal (which won’t take long!) and book your ticket. You will eat well, be overwhelmed by history and beauty, and leave a changed person. I know I did.

Leave a Reply

Your email address will not be published. Required fields are marked *