For ten days over the Christmas break, we explored the bright, colorful, and I can not stress this enough, hilly city of Lisbon, Portugal. It was a fantastic time to visit the coastal capital of Portugal, the air was filled with the holiday spirit and the streets hung with twinkly lights. We even stumbled upon a Christmas Market, proving that dreams really do come true. Lisbon has a relaxed and unpretentious vibe and visiting during the winter meant no wait times or crowds. The people were friendly, the weather was temperate, and the tile, THE TILE!

One of the oldest capital cities in the world (Lisbon pre-dates Paris, London and Rome), Lisbon’s history is long and storied. Archeological fortifications found on Lisbon’s Castelo hill date back to the 2nd century BC and finds dating from the 8th and 6th centuries BC have been attributed to settlements from the Iron Age. Celtic, Phoenician, Greek, Roman, Moorish and Spanish rulers have all, at one time or another, called Lisbon home and the influence of their cultures are still evident today in the architecture of the city.

Typical House Colors


As a port city, Lisbon was a hub of trade and exploration. During the Age of Discovery, the country sent ships on expeditions abroad in search of undiscovered lands and established the Casa da Guiné e Mina, a hub of warehouses and custom offices for trade. As a result, German, Flemish, Dutch, English, French, Greek, Lombard and Genoese traders flocked to Lisbon to set up posts, bringing the city wealth and power.

Christopher Columbus visited, Napoleon invaded, and one of the largest and most devastating earthquakes ever was recorded (1755). During World War II, Lisbon remained a neutral and open port, allowing many Jews to escape Germany and find safe passage to the United States. In 1940, Portugal hosted the Portuguese World Exhibition to celebrate the 800th (!!) anniversary of it’s founding (1140) and it’s 300 years of independence from Spain (1640). The exhibition resulted in the commission of one of Lisbon’s most notable and recognizable monuments, the Padrao dos Descobrimentos (Monument to the Discoveries). In 1998, Lisbon hosted the Expo ‘98 World’s Fair and the grounds of the expo, now called the Parque das Nações (Park of the Nations), are home to Lisbon’s Oceanarium (the largest indoor aquarium in Europe) and the Vasco da Gamma Bridge (the second longest in Europe at 12.3 km), both built for the “The Oceans: A Heritage for the Future” themed expo.

The city is built on seven hills and it certainly felt like we climbed every one of them during our stay, repeatedly. But between the sangria and the Pastéis de Nata, it likely didn’t do me any harm to squeeze in a few good hill climbs. Easily one of the most picturesque cities we’ve visited, there seemed to be an Instagram-worthy shot around every corner. So, without further ado, here are my recommendations for what to see and do in Lisbon.

Where to Stay

Príncipe Real

We stayed in a beautifully furnished and well located Airbnb in the Príncipe Real area of Lisbon. This area is known for its restaurant scene and there were at least 10 choices within blocks from our place. It was about a ten-minute walk to the metro or train station and shopping but those walks always seemed twice as long because of the number of times we’d stop for photo ops. If we had it to do over, we’d stay here again.


This is one of the oldest and most picturesque areas of Lisbon. It is with the deepest regret that I tell you we left Alfama until the last day to explore and by that time, we were tired, hungry, and so very sick of hills. Although we had wandered through Alfama on our way to visit the Castelo de S. Jorge and the Lisbon Cathedral (go there too!), we really wanted a chance to take our time and wander the narrow, winding, and colorful cobblestone streets. This ancient district is the oldest in Lisbon, the birthplace of Fado music and would make a lovely home base for time spent in Lisbon.



Other Areas


This area was devastated by the 1755 earthquake and subsequent tsunami. It was rebuilt and is now one of the first examples of earthquake resistant architecture. Baixa is a busy and popular tourist district, home to shops, hotels as well as some of Lisbon’s main tourist attractions. A great place to wander.


Great shopping, cafes and monuments. This picture of the statue of Portuguese poet António Ribeiro, which sits in Chiado Square, was taken on New Year’s Day. The wine glass and bottle fit so perfectly with Ribeiro’s gesture, we almost didn’t realize they weren’t meant to be there.

Poet Antonio Ribeiro


Bairro Alto

Known for its night life, Bairro Alto is where you’ll find the best bars and Fado restaurants.


See What to See and Do



During our ten day stretch, the weather was warm and sunny almost every day with temperatures ranging from 11 to 16 degrees Celsius. The winter months in Lisbon can be rainy, but lucky for us the worst weather we had was an overcast 11-degree day. After shivering our way through the North Sea wind in Amsterdam a few springs ago, we were slightly concerned about wind from the ocean, but most days there wasn’t even a breeze. In other words, perfect conditions for my “try to look local” uniform of sweater and dashing scarf.


What to See and Do


Belém, meaning Bethlehem, is the site of one of the first, and arguably one of the most important, ports in recorded history with mentions dating back to 1295. The district was the very birthplace of the Age of Discovery and, as such, is home to some of the most historic monuments in Lisbon. A day can easily be spent sightseeing and walking the pathway that runs along the Tagus River estuary between the Monument to Discoveries to the Tower of Belém and beyond. Just make sure you leave time to grab a couple of Pastéis de Nata at Pastéis de Belém, their tarts are some of the best in Lisbon.

Pastéis de Nata


Mosteiro dos Jerónimos (Jerónimos Monastery)

Construction on the Jerónimos Monastery began in 1501 and finished approximately one hundred years later. Considered to be one of the finest examples of Manuline architecture, so named for Manuel I the first ruler of the Avis-Beja dynasty who commissioned the monastery as an everlasting monument to the dynasty. Yep, you read that right. Manuel commissioned the monastery to be built in honor of his rule, had a style of architecture named for him, and then filled that monastery with monks whose main purpose was to pray for his soul. Maybe I’m being a little hard on Manny, because the Jerónimos Monastery is rather spectacular and includes access to the Church of Sta. Maria. The church houses the tombs of several of Portugal’s kings and of Manuel I’s children as well as the tombs of both Portugal’s greatest explorer, Vasco da Gama and it’s greatest poet, Luís de Camões.

Cloisters at the Jerónimos Monastery


Padrao dos Descobrimentos (Monument to the Discoveries)

Commissioned for the 1940 Portuguese World Exhibition, Monument to the Discoveries was originally sculpted using gypsum. It was later restored using cement and Leiria stone and the figures were carved with limestone from Sintra. The monument is bold, imposing and inspiring; it is a monument to Portugal’s Golden Age of exploring and trade and is situated in the exact place where many voyages of the Age of Discovery began. There is a small museum inside the monument and a viewing platform with views over the Tagus estuary. It is a great place to get a good look at the Ponte 25 de Abril suspension bridge, sister bridge to San Francisco’s Golden Gate Bridge, and to catch a glimpse of the Cristo Rei watching over the city of Lisbon from the south side of the estuary. The day we visited was warm and sunny making an enjoyable 2 km walk along the river pathway that runs between the monument and the Torre de Belém.

Monument to the Discoveries


Torre de Belém (Tower of Belém)

The Tower of Belém was finished in 1516 and used as a bulwark in the defense of the port of Lisbon. The tower is accessed by bridge and entered by crossing the drawbridge that is the tower door. Once inside, visitors can see cannons positioned at cannon holes along the interior wall, behind them is a central open-air courtyard that allowed for the ventilation of cannon smoke. Visit the very low-ceilinged dungeons in the basement and climb the stairs to the tower overlooking the Tagus estuary. My favorite part of the tower was the bulwark terrace where you could slip into one of the projected turrets and imagine the ships of weary explorers returning to the harbor after a long journey, looking to catch a glimpse of the statue of Our Lady of Safe Homecoming on the parapet of the tower.

Tower of Belem


Calouste Gulbenkian Museum

Many of you know how I feel about art museums. Some of you have even had to endure visits where I kept you from eating for extended periods in order to really let my art history freak flag fly (again, I truly apologize Michelle). So, it will come as no surprise when I say that I absolutely loved this museum. At this point, you may be asking yourself if I’ve ever met a museum that I DIDN’T love and, well, the answer would be no, but there are definitely some that I’ve loved more than others. This is one of them.

The museum was named after Calouste Gulbenkian, an Armenian and avid art collector who made is money in oil. Gulbenkian arrived in Lisbon during the second world war, leaving behind residences in Istanbul, Paris and London. After his death in Lisbon, a foundation bearing his name was established to care for his “children” (if I am ever lucky enough to amass any sort of art collection, you can bet that I too will most certainly refer to the pieces as my “children”), a large and impressive collection ranging from antiquities and sculpture to Frans Hals and early 19th century masterpieces by Manet. The museum opened in 1969, and has continued to expand on the original “Founder’s Collection” adding the Modern Collection and has become known, fittingly, for its significant collection of Portuguese art.

I’m sure due in no small part to the time of year, we pretty much had the run of the place allowing as much time to be spent admiring the works as we could bear. Some of us held up longer than others, and after finally scraping our children off the last of the contemplation benches (where the only thing they were contemplating were the answers to the BuzzFeed quiz they were taking) I knew in my heart that the least I could do was take them to an aquarium.

Calouste Gulbenkian Museum


Oceanário de Lisboa

Admittedly, I’m not much of a zoo person and I had never set foot in an aquarium, so I can’t say I was dying to go to the Oceanário, but it was our son’s 14th birthday and he could not have been more excited. My attitude changed completely when we arrived at the first exhibit. We were lucky enough to catch the tail end of Forests Underwater by Takashi Amano and it was one of the most beautiful things I have ever seen. Takashi Amano was a landscape photographer who created a 40-metre-long aquarium that holds 160 thousand litres of fresh water. Forests are literally submerged into the tank and fresh water tropical fish wind their way through the foliage while music specially composed for the exhibition plays. Magical doesn’t even begin to describe it.

After reluctantly leaving the Forests Underwater exhibit, we continued on through the aquarium, immediately encountering one of those massive, multi story wall tanks with sharks, sting rays, and fish unlike any I’d seen before. It was completely mesmerizing. We saw penguins, a little mini shark showing off in a pond, and the most designer-y of all marine life, the Jelly Fish, so graceful and delicate. But I have to say the real show stopper was the otters. Hilarious, adorable and so full of life, we probably spent a little too long enjoying their antics and watching them be fed. The whole aquarium experience was definitely a highlight, and that’s coming from me.

Forests Underwater by Takashi Amano


Castelo de S. Jorge

This fortification sits high above the city of Lisbon on Castelo hill, and was built by the Moors in the mid 11th century. Archeologists have found evidence of human life on Castelo hill dating back to the Iron Age (which began in 1200 BCE). In both Lisbon and Sintra we ran into these little food truck vehicles called Wine with a View that sell glasses of white, red and rosé, to drink as you gaze out over the city. I thought this was just about the best idea ever until I started walking the ramparts approximately 3 stories from ground level with shin high barriers to death and stairs so steep I wanted to go down on my bum. Imagine how impressed I was with the lady descending the stairs in front of me wearing skinny jeans and stilettos while balancing a glass of wine and carrying a large handbag. Not all heroes wear capes, people. But in all seriousness, the Castelo was one of my favorite places, the view was spectacular, the grounds amazing, and the fog rolling in from the ocean provided even more atmosphere to an already cinematic setting.

Wine with a View



About a 40-minute train ride from Lisbon, the city of Sintra, a UNESCO World Heritage Site, sits perched in the hilly Portuguese countryside. Sintra has long been a summer escape for the wealthy and the royal which accounts for its high concentration of palaces, castles and lush, sprawling parks, most of which are also classified UNESCO World Heritage Sites. We spent a day in this picturesque playground but could easily have spent more as we saw only a fraction of what it has to offer.


Castelo Mouros (Moorish Castle)

The Moorish Castle is nestled high in the hills of Sintra. The castle was built sometime during the 8th century by Moorish troops occupying the Iberian Peninsula. On the morning we visited, the mist was still clinging gently to the hillside and the sunlight filtering through it gave the whole place an ethereal feel. The views of the surrounding hillside are incredible, and the neighbouring castles can be seen in the distance. Inside the castle walls, pathways lead from section to section and large boulders sit amidst lush foliage. In the west wall of the castle you’ll find the Door of Betrayal, a small point of entry allowing enemy access or escape. Although almost nothing remains of what was inside the castle walls, with the exception of a few walls in the castle keep and the cistern, these atmospheric ramparts were well worth the trip.

Ramparts of Moorish Castle


Palacio Nacional da Pena (National Palace of Pena)

Bold, colorful, irreverent, the National Palace of Pena is a spectacle. Built in the Romantic style of architecture, the palace has been home, since the Middle Ages, to the Our Lady of Pena chapel built on the site after an apparition of the Virgin Mary. In the 15th century King Manuel I (remember him?) commissioned a monastery to be built on the site for the monks of the Jerónimos Monastery, and in the early 19th century, King Ferdinand II acquired the earthquake ravaged monastery and decided to construct a palace to be used as the summer residence of the Portuguese royal family. In 1910, the palace was declared a national monument and in the 1990’s it was restored to its original glory as the vibrant colors had long turned gray with age. We didn’t pay to visit the palace interior, but the exterior and grounds were spectacular and like nothing we’d ever seen before. My first impression was that of a theme park castle, the bright yellow, red and periwinkle blue making for an unusually unreserved royal residence. However, bright hues and vividly patterned tiles are so integral to Portugal that somehow you just can’t image a royal palace of any other kind.


Quinta da Regaleira

I’ve saved the best for last. The Quinta da Regaleira was my favorite of the three places we visited, much smaller in scale and much more recent, finished in 1910. Situated in the city of Sintra, the mansion was built by Carvalho Monteiro, also known as Moneybags Monteiro, and designed by Italian architect and set-designer Luigi Manini. Unfortunately, the upper floors of the mansion were closed for renovation, but the main floor was no disappointment: carved wood coffered ceilings, mosaic tile and parquet floors, original wallpaper, and painted murals. I would have given my left arm to have seen the kitchen, visions of Mrs. Patmore danced in my head. In addition to the mansion, the grounds feature a chapel, a network of tunnels, several lakes, extensive footpaths and, much to my delight, a little something called the Initiation Well. This inverted tower plunges deep into the ground, a 27-metre spiral staircase allowing visitors to wind their way to the bottom to see symbols most commonly associated with the Knights Templar. These wells were never used to hold water but were meant for ceremonial purposes, the number and spacing of stairs having direct links to the Tarot. The entrance to the Initiation Well is unassuming to say the least, nothing more than a narrow opening between rocks, giving no clue as to what’s in store. As this was our last stop of the day, we didn’t get to spend as much time as we would have liked exploring the grounds but trust me when I say this is a must see.

Quinta da Regaleira


The Initiation Well



So disappointed we weren’t able to make it to Porto. I have heard nothing but great things about this vibrant and historic city and I hope to make a return trip to Portugal for the express purpose of visiting it (and Cascais, and Algarve).


What Not to Do: An Unpopular Opinion

I have one tip, and one tip only. Don’t ride Tram 28. Although we took many tram rides while in Lisbon, they can be an absolute lifesaver when faced with dragging yourself up yet another steep hill at the end of a long day of sightseeing, I really wouldn’t recommend riding the iconic Tram 28. Pick literally any other tram to ride and you will have the same, but likely better, experience. Why? Tram 28 is SO. BUSY. We visited Lisbon during the off season and still waited in line for at least an hour to board the tram. By the time it was our turn to board, the only seats left were priority meant for those who require a seat. This meant we stood the entire ride, which was fine, but it also meant missing the historic sights the tram was known for passing. The trams have a seated capacity of roughly 24 with the remaining space standing room only, and that standing room is packed. And just when you think it can’t get any more packed, the tram makes its next stop and more people hop on. There are many other tram routes to enjoy, and the experience of riding one really shouldn’t be missed. It is an inexpensive (€2.90 per person for two trips or €6.30 for a 24-hour ticket) and fun way to get around the areas of Lisbon not accessible by Metro. By all means, take that iconic Tram 28 Instagram shot, just don’t ride it.

Historic Tram 28


What and Where to Eat

I do believe I may already have mentioned sangria and the Pastéis de Nata (Portuguese custard tarts) and if it was possible to subsist on those alone, I would have. One of the best pieces of advice we were given by a local was, when looking for an authentic Portuguese experience, look for a place that is lacking in design savvy, which is to say it looks the same today as it did twenty years ago, and serves pan fried fish for no more than €10. Excellent advice that never let us down. We had fantastic Mexican food at El Clandestino (which also had a bar called Frida, as in Kahlo), and for our son’s birthday meal we went to Jamie’s Italian, which was just at the top of our street. It was really delicious, and the restaurant design was pretty great too. The only regret I have restaurant-wise was that we didn’t make it to A Cevicheria, which we passed almost daily, known as much for it’s ceviches and Pisco Sours as it is for the giant octopus that hangs over the bar.



At the tippity-top of my shopping destination list sits A Vida Portuguesa, a charming boutique with three locations in Lisbon and one in Porto. A Vida Portuguesa carries an assortment of quality products that are made in Portugal and have been around for generations: ceramics, textiles, gourmet food items, jewelry, books, housewares, and stationery to name a few. The stores themselves are beautifully designed, the interiors in keeping with the character of their products: established, timeless, effortlessly chic. I visited two of the locations while in Lisbon and if we’d have been there a few more days, I would have gone to the third.

Next up is the oldest bookstore in the world, Livraria Bertrand. My love of  bookstores rivals my love of art museums and this store’s carved wood shelving and sections connected by barrel vaults made it the physical embodiment of the bookstore of my dreams. If only I could read Portuguese.

A major benefit of travelling after Christmas is the post holiday sales. European staples like Zara and H&M had major sales as did Portuguese department store El Corte Inglés. We popped into any shop that looked vaguely interesting, which is how we stumbled upon Chi Coração, a lovely little store carrying Portugal-made woven wool blankets and scarves. Needless to say, there was no shortage of places to shop, and I didn’t even make it to the antique Portuguese tile shop I was dying to see or to Embaixada, which was in our neighborhood but I somehow managed to miss. It’s probably for the best…Clint’s best.

Finally, a special mention to the Calouste Gulbenkian Museum Shops (Oh yes, there’s more than one!), where I literally had to tell myself “No, Regan. No.” to the amazing selection of art books and decorative items.


Livraria Bertrand


That’s It!

I guess if I haven’t convinced you to visit Lisbon by now, there’s nothing really left to say. I hope you’ve enjoyed this record length post and that maybe it’s given you just the nudge you needed to consider Portugal your next vacation destination, you won’t regret it.



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