Portugal: Lisbon & Sintra City Guide

While waiting patiently to find my seat on my first TAP Portugal flight – as everyone, ever so leisurely, stores their belongings overhead – my ears perk up the moment the stewardess begins her announcements in a language I have yet to hear. 

Rather than feeling lost and overwhelmed when unable to understand, I immediately feel encouraged and compelled to learn the language and norms of the Portuguese. I even find a bit of tranquility in it all. And just as I finally make it to my seat, I realize this is where I find my comfort. Not at home, but in the unknown.

After a 6-hour flight full of free wine, but lacking in sleep, I arrived at 7am local time in Lisbon (2am est). With a few hundred pounds of luggage and eight hours to kill until my Airbnb check-in, I found myself in the middle of Rossio Square deciding my next move.

Just when I thought I had escaped the paparazzi in Asia, I looked to my right to see a few fellow tourists snapping my photo as I sat on one suitcase and rested my legs on a pile of others (in hindsight, I guess it was a bit of a sight to see).

Rossio Square
Rossio Square

With no locker luck (nothing big enough), I opted to cause a minor scene at the restaurant next door, Confeitaria Nacional, by lugging all five bags up their semi-spiral stair case during morning rush and proceeded to sit there for breakfast… and several hours more.

Full disclosure – I sat in Confeitaria Nacional for so long, wishing we could be outside exploring sans bags, that I took about 48 variations of this photo out of pure boredom.

Dazed and overtired, I finally arrived at my quaint Airbnb apartment in the heart of Lisbon’s oldest and most picturesque neighborhood, Alfama, where I immediately proceeded to take a long overdue nap.

Technically, this trip to Portugal was only an extra long layover; a stopover. TAP Portugal offers free stopovers when booking a flight with a layover in Lisbon. I chose the longest option – 72 hours – and it didn’t even take me that long to fall in love with the city.

With so much to see in so little time, I clocked over 50,000 steps in three days. Only ever stopping to take in the sights, snap a few photos, get a tapa (small bite) or two, or take a siesta before seeing Lisbon by night.

The Tram 28 runs through the city day and night, sharing its tracks with cars and motorbikes.

While three short days doesn’t make me an expert by any means, here are the few places to see, eat, and explore I felt worth writing home for.


Neighborhood: Alfama

As the second oldest in Europe, Lisbon’s medieval district, Alfama, is found just on the outskirts of the bustling downtown area. Walking aimlessly through the labyrinth cobblestone streets seems to be the best way to take it all in. Vibrantly colored tiled buildings complete with window boxes overflowing with greenery line the alleys, and every so often a peak through just the right one can give a glimpse straight through to the mouth of the Rio Tajo (Tagus River).


Just after dusk, you can hear the faint sounds of live, traditional Portuguese Fado music coming from cozy wine and tapas bars. Wander into any for a taste of authentic bites accompanied by glasses of wine, too delicious for the price you’ll pay.  

If you’re looking for a quieter location, with an easy walk to all the action – Alfama is it – and I can’t recommend our Airbnb enough (more info at the end of the post)!



img_5715Castello de Sao Jorge at sunset
R. de Santa Cruz do Castelo, 1100-129 Lisboa

Well known as the best place to see the sunset over Lisbon, Castello de Sao Jorge is a must see 11th century Moorish castle overlooking the layers of clay-tiled roofs leading down to the city center.

Be on the lookout for the beautiful peacocks roaming the grounds!

Arco Triunfal da Rua Augusta
R. Augusta 2, 1100-053 Lisboa


Not far from Alfama or downtown Lisbon, it’s hard to miss the Rua Augusta Arch. Originally built to showcase Portugal’s wealth to incoming traders, the arch is now a staple of splendor for all visitors. Take in the elaborately detailed architecture, then walk to the adjacent waterfront where you’ll find stairs leading into the Tagus. Accompanied by a chill vibe, thanks to live musicians and sand sculptors posted up alongside the small strip of beach, its the perfect place to take in the 360° view.



Santa Justa Lift 
R. do Ouro, 1150-060 Lisboa

Between the arch and Rossio Square, look up for the Santa Justa Lift.  Skip the long lift lines to the top and get the real views from Castello de Sao Jorge instead. ⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀


Food & Drink

Turn down almost any side street in Lisbon and aromas of freshly baked bread from the padarias (bakeries) consume your senses, luring you right in. Feel warm and welcomed as your waitress sings along to the live music while pouring you a glass of the perfectly aged red wine. A precious place where even a small market stall takes the time to make a proper sangria, freshly sliced fruit and all.

R. Tomás da Anunciação 63, 1350-166 Lisboa
Serving up croissants filled with anything of your choosing – sweet or savory – complete with  jugo naranja fresco (fresh OJ…to die for). Giallo is the perfect place for both café and breakfast or artisan gelato for dessert. 


A Gingha 
Largo de Sao Domingos 8 |1150-320, Lisboa

Stop in this famous, hole-in-the-wall bar just northeast of Rossio Square for a sweet shot of traditional Portuguese liquor made from infusing gingjas (sour cherries) in alcohol.

My said, freshly mixed sangria, complete with a cinnamon stick!

Mercado de Fusão
do, Praça Martim Moniz, 1100-341 Lisboa

This lively square has a taste of Portuguese and international fare. Several food stands, Japanese to Mexican, surrounding the sunny seating, makes this the perfect place for a quick drink or bite to eat while resting your feet.

Primo Basílico
R. dos Remédios 37, 1100-441 Lisboa

Vegan pizza alert!  With owners from Italy, these slices are authentically appetizing, with toppings ranging from traditional margherita to mushroom artichoke pesto. ‘Real’ cheesy and non-vegan options are available too!
(I didn’t even stop to take a photo before devouring, so you know its good.)

Marcelino Pao e Vinho
Rua do Salvador 62, 1100-466 Lisboa


Post-nap on my first night in Lisbon, I wandered the small alleyways of Alfama and began to follow the sound of acoustic Beatles, which brought me to this hidden gem, Marcelino Pao e Vinho.

As I peaked in through the glass windows, a kind waiter caught a glimpse and came to the door to welcome me in. I sat and had a hearty red wine and warm bread just inches away from the musician, sitting alongside a big family seemingly finishing a long, filling, and loving dinner.


Princesa do Castelo Restaurante Vegetariano 
Rua do Salvador 64A, 1100-466 Lisboa

I must admit it isn’t always easy when it comes to being vegan. I have a hard enough time ordering limited options in the States, let alone abroad, so, when I came across Princesa de Castelo, I was in heaven.

Serving up a few plant-based dishes on their daily menu, this warm and inviting restaurant with a cool, English speaking staff is a must try, vegan or not. The Kung Pao rice with tofu was better than any I’d had in Asia and when my waiter asked if I wanted ‘Chocolate Salami’ with my espresso, I was able to say yes without hesitation, knowing it was safe. The fudgy – salami-shaped – dessert was the perfect ending to the best meal I had in Lisbon.

Cinco Lounge
R. Ruben A. Leitão 17A, 1200-392 Lisboa


To switch up the copious amounts of wine, head to Cinco Lounge. An upscale cocktail bar with unique drinks worth paying the price – and still cheaper than New York City vodka soda prices.

Order any cocktail on the menu and it’s always a surprise as to how it’ll be served. In a simple cocktail glass, on fire, or in a “soup-style” can, freshly sealed, only to be opened right at your table. My drink to the right was a bourbon cocktail of sorts, made using a gassing chamber, served upside down and pressurized, allowing the drink to siphon out as I sipped.

Confeitaria Nacional
Praça da Figueira 18B,
1100-241 Lisboa, Portugal

Previously mentioned, a great cafe in Rossio Square if you need to sit for several hours with luggage and/or try some traditional Portuguese pastries.

Ordering Tips:
*On many menus you may see 1/2 dose or 1 dose as options for salads and entree plates. A half dose is usually plenty for one and a full dose can be shared by two.

*The next size up from a glass of wine, is usually 1/2 to 1 liter, if not the full bottle (definitely not complaining).

fullsizerender-6*Airplane Food Tip:
Order a special meal, even if you’re not vegan/vegetarian… my food always gets served first – and so far, our meals have always looked better than the standard ones – served after we’ve already finished.


Affordable clothing, shoes, and souvenir shops can be found all over town, especially surrounding Rossio square. But head to the Tuesday & Saturday flea market, Feira da Ladra, for an eclectic mix of local vintage finds scattered throughout detailed, century-old tiles and knickknacks.

Feira da Ladra
Campo de Santa Clara, 1100-472 Lisboa


If you choose to surpass the dimly lit streets of Alfama after dusk, tourists and local partiers tend to head to The Pink Street. The discotecas bring the crowds, as the street gets livelier late into the night. If you want to fit in, don’t bother arriving before midnight.


Rua Nova do Carvalho
1200-371 Lisboa

I stumbled into a small bar I overheard playing live English music and met a traveling couple from the States, whom I agreed to migrate with for another round of drinks. In attempts to find a ‘level 1 discoteca’ (we joked, not ready for the full ‘level 5’ party scene) I suggested a place recommended by our Airbnb host, Pensão Amor.

Pensão Amor
R. do Alecrim 19, 1200-014 Lisboa

It didn’t take long for us to notice the decor, hinting that the place was once a brothel. Our inclining was later confirmed after realizing us girls had seemingly been ’em exibicao’ (on display) in the bathroom, per the sign above the door. Inside the restroom, the decor matched the theme, with a Barbie and a bullet positioned in an assuming manner.  We left soon after, in attempts to find a classier place, only to see the entrance queue taking over Pink Street. Apparently, the place to be, as long as you don’t mind possibly being watched while you pee.

After our night searching for the perfect music, we decided the restaurants have better music than the disotecas – most of which we opted out of when the music choice was ’70s/80s techno’ – being played on…CDs.

Escape the City to Sintra 


Sintra, Portugal 

A day trip to Sintra is an absolute must, whether you have one day or twenty in Portugal. A town well deserving of its own post, where centuries-old castles and palaces line the Sintra Mountains.

Just forty minutes north of Lisbon, take the train for only €5 roundtrip, with a 20-minute walk from town to the sights. Or, splurge with a €30 uber all the way up from Lisbon – this will save you a hike up the mountain – and then opt for the cheap train ride home.

Parque e Palácio Nacional da Pena
Estrada da Pena, 2710-609 Sintra


The story of Pena Palace dates back to the Middle Ages when its construction atop the Sintra Mountains began, making its mark as the first center of the artistic Romanticism movement. I spent about two hours exploring the grounds, built quite literally into the rocky terrain, and admiring the original interior decor throughout its lavish rooms. Looking out upon the breathtaking details and vast views from the Queen’s Terrace, I couldn’t help but feel like a Queen…even if only for the day.

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Castelo dos Mouros
2710 Sintra

Enjoy the panoramic views from the winding staircases of this medieval castle. I found myself in disbelief that a castle so old and so vast has stood the test of time. And as I left the magical town of Sintra that day, I found myself believing in fairy tales again.

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Incredibly affordable at under $40 a night, our small, yet spacious, apartment was equipped with everything we needed for a short stay. Our host, Andreia, was exceptionally helpful and responsive, completing the package.

She welcomed me with a book of everything to know about Lisbon’s hot spots, and was so responsive, that when I accidentally left the keys upstairs in the midst of checking out, she was able to write back via message in less than a minute with the door code, and the ‘I’m going to miss my flight’ crisis was averted.

You can check out Andreia’s place here! If you’re new to Airbnb, sign up here and receive over $30 off your first trip with this promo code!


Thus far in Europe, I’ve found Airbnb’s are much cheaper than what’d you’d get for a decent hotel, more updated, and gives you a sense of being a local.

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My wonderful, whirlwind exploration of Lisbon was over too soon. If I had to choose one major take away from this country, it would be the genuine love for life that can be felt at every turn. Where instead of ‘goodbye’ it’s ‘enjoy life’ & graffiti-ed streets act as daily reminders that love – for oneself, each other, and everything in between – is all there is.

I’m taking off on my second flight of many, with my heart full. Obrigada, Lisbon.

4 thoughts on “Portugal: Lisbon & Sintra City Guide

  1. in 72 hours you’ve seen a lot of Lisbon and Sintra, well done 🙂 I live close to Cascais, which is also a great area to visit, specially in the summer, to go to the beach eheh happy week, PedroL


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