After the delights of Porto and walking the Portuguese Camino, I knew I wanted MORE TIME in Portugal.
The next walking adventure I planned in Portugal was the surprisingly perfect Rota Vicentina! In fact I have spent so much time documenting the Rota Vicentina on this blog that I have neglected my city visits to Portugal (until now).
But if you are looking for your next beautiful trail to walk, please add the coastal Fisherman’s Trail to your list. What’s wild is that my first days on that trail were really just an add-on to a trip to Lisbon that I had planned with my sister, a happy, fortunate find after some city wandering.
Since that first trip, I have returned to Lisbon two more times, so this collection of photos and ramblings is from all three trips: January 2023, March 2023 (yes, I went RIGHT back two months later!) and December 2024/January 2025 (New Year’s).
I honestly didn’t expect to love Lisbon as much as I loved Porto. But after my first trip to Portugal, I read Night Train to Lisbon (also a film) and The Night in Lisbon, and I knew I had to go for myself and see Lisboa, (which I learned to pronounce properly by listening to Portas do Sol on repeat after Shazam-ing it in a cab in Porto).
As soon as I realized that Lisbon was a city with which I wanted to become acquainted, I asked my sister, Anna, to meet me there. We both were smitten from the start.
One of the best ideas we have ever had is to meet somewhere in January after all of the holiday hullabaloo has passed.
We put our trip to Lisbon on calendar in late September. We bought plane tickets and I made reservations for the city and for a few days of walking afterwards. Then we put our heads down, kept our busy autumn schedules with high school boys and an even busier Christmas season with college and adult kids visiting.
I tend to be a little numb after the holidays.
I think it’s as much a product of the historical holiday drama as it is any of the actual current events. I’m always trying to disrupt my usual Christmas pattern of unrealistic expectations followed by an inevitable disappointment. I have tried moving Christmas celebrations to neutral locations, pretending it’s not really December, and on other years, going all in on what everyone else in my family wants to do, but none of my strategies seem to “work.” Christmas is a time that I simultaneously dread and look forward to. Then when it has come and gone, I am both sad and relieved. And these paradoxes seem to show up every year no matter what I do.
So honestly, I wanted to just crawl in bed for a couple of days (or all of January) after the holidays were over in 2022. It was our first Christmas in our new home in Bristol. It had been cold, dark and rainy. And decidedly anti-climatic.
But instead of getting in bed, I packed my backpack and hopped a flight to Lisbon.
Again…SUCH a good idea!
I arrived a day before Anna, which I spent dodging the rain at Calouste Gulbenkian Museum, an astonishingly varied art collection amassed by one man in his lifetime, in the midst of escaping multiple wars. (Sidebar: I’m adding collecting art and then making it public for all to see to the list of things I prefer that wealthy people do with their money – right up there with building libraries, schools and theaters – instead of increasing military surveillance, shutting down entire cities for personal events, taking eight minute flights on private jets, and funding fascism.)
I often “meet” a city for the first time in the rain. Maybe it’s because I prefer cities in winter when they are less crowded, but I have wandered Paris, Siena, Edinburgh and of COURSE Bristol in the rain.
That’s why hiking boots are the BEST travel shoes.
This is especially true in Lisbon where the streets are made of marble cobblestone!
Even in hiking boots, I had a few near misses on the slick cobbles.
They are EXQUISITE though.
The cobbles were the first thing about Lisbon I noticed (after the easy metro ride from the airport).
I emerged from the underground into a square covered in these black and white cobblestones. I snapped lots of photos of all the different patterns. A city so dedicated to the artisan work that maintaining these streets requires is one that puts a high value on art.
There is even a monument to the craftspeople who maintain this extensive network of art on the ground.
In Rossio Square, the cobbles are laid in a pattern that is meant to make you feel like you’re on the waves of the sea, a nod to Portuguese maritime history.
The center of Lisbon is a flat section of squares and streets on a grid. This area is surrounded by hilly neighborhoods that rise up around its edges, and all of it is bordered by the Tejas/Tegas River that flows from the ocean.
The grid-like center of town was built in such uniform structure after an earthquake flattened the city in 1755.
We stayed at the Pessoa Hotel, which is named for one of Portugal’s most celebrated writers, Fernando Pessoa.
The hotel was located on the hill west of Rossio Square, near the Chiado district, where we enjoyed rooftop breakfasts while looking out over the city.
From the hotel, it was a short walk down cobbled steps into Lisbon’s main thoroughfares.
On the way down from our hotel each day, we would pass a window where they were serving warm Pasteis de Nata. And of course, we would always stop for one!
The pastel de nata, immortalized by Emma Stone in Poor Things, is a Portuguese Egg Custard Tart that is available on just about every corner in Lisbon.
We ate SO many of them, not all at once, but here and there at different bakeries. I love them warm (and they were always warm at this little window), but my favorites were the ones from Belem, out by the Jerónimos Monastery where the monks started making them in the 18th century.
In the 18th century, nuns and monks were using a copious amount of egg whites to starch their habits and robes. So they invented the best treats with the leftover egg yolks, pasteis de nata being the most famous one. But we tried many other egg yolk treats and our favorites were some little cookies from the national bakery in one of the main squares of Lisbon. I returned to this bakery for a little box of treats on every trip to Lisbon.
On my second trip to Lisbon, with three friends in March 2023, I think we ate even MORE of these tarts than on my first trip. My friend Kristie LOVES them and she was keeping track of which ones were her favorites.
I still held to the best ones being from Belem, which I confirmed again a year later when there with my family. They have the flakiest crust! When I think about the warm filling topped with a little sprinkle of cinnamon and sugar, my mouth starts to water!
Honestly, you could easily book a trip to Lisbon just for the food, especially if you love seafood and fish. I think the best seafood I’ve ever eaten has been on trips to Portugal, washed down with a glass of Vinho Verde, another uniquely Portuguese experience.
Next to the Pasteis de Belem, is the Jerónimos Monastery, which Anna and I visited together.
It’s one of the main attractions in Lisbon, and it’s definitely worthy of its spot on all the Lisbon Listicles. When we came back in March, the lines to see it were so much longer, so I recommend visiting in winter when it is quiet and the line to get in is short.
Deep within the quiet cloisters of the monastery, we walked by Fernando Pessoa’s simple tomb.
It is quite the contrast to the sculptures inside the neighboring church of Santa Maria that celebrate Vasco da Gama and other “heroes” of Portugal’s colonial expansion.
The monastery and church were built with money from Vasco da Gama’s and other Portuguese explorer expeditions. If you were traveling along the river from the city to the ocean, you would pass the monastery last, and hope that your contribution to its beauty would keep you safe at sea.
The unique Portuguese Gothic architecture has elements of a ship built into it.
I do love a cloister and I found the ones in the monastery to be as beautiful as any I’ve ever seen.
I could have wandered these courtyards in silent prayer for days, but the ship ropes in the arches and other nautical elements were a reminder that the Portuguese empire was built on exploration, and exploitation. It’s a troublesome history that includes the origins of the Atlantic Slave Trade.
In fact, it was a Portuguese man (Gomes de Zurara) who came up with the construct of race. He literally invented “blackness” (and then also whiteness) in order to justify the slave trade. His writing was actually commissioned by slave-trading leaders in Portugal in the 1450s in order to justify their subjugation and trafficking of people whom they deemed lesser than themselves.
Portugal is a stark reminder that all empires DO eventually fall. Portugal’s post-empire phase was long and rough, including 45 (!!!) changes of government between 1910 and 1926, which was followed by Western Europe’s longest-lived dictatorship.
A right-winged, authoritarian regime suppressed civil liberties and political freedom until a (mostly bloodless) coup in 1974.
In 1940, under Salazar’s dictatorship, Lisbon hosted the Portuguese World Exhibition where a statue of explorers was built to celebrate 800 years of Portuguese exploration. Then in the late 50s, the regime built a larger, permanent version of the statue overlooking the river called the Monument of the Discoveries.
The explorers represented on the statue include Vasco da Gama, and even the writer Gomes de Zurara got a spot on the boat. Standing beneath the structure, I was reminded of Confederate War monuments, and how many of them were put up in the southern United States during the civil rights movement of the 20th century, actually at the same time this statue was being built. Revisionist odes to a history that could only ever have meant success for a few at the cost of the many.
Listen closely and you can almost hear Salazar whispering back in 1960:
Remember when we were great.
Don’t pay attention the slums, to the growing poverty, to how filthy our capital city has become. Instead look at this bright shiny statue and celebrate when we were great.
As humans, we are so easily sold a stories about the past. What fools we are.
But look at Lisbon and Portugal now: an example to all of us about how to learn from our mistakes, however slowly.
I would argue (from my extremely limited perspective) that Portugal is as great as it has ever been, and looking towards a bright future.
And it’s not just because of those shiny tiles and artisanal cobbles!
Portugal has made some WILD decisions as a nation to actually build a society that is for the many, rather than for the few.
They’ve done some research about what works well for communities, and here’s the crazy bit…someone in power actually paid attention to the researchers!
They have implemented some of the most progressive and exciting changes in the world. For example, in 2001, Portugal made the stunning decision to decriminalize drugs. All drugs are not legal, but the possession of drugs is not treated as a crime.
Instead of spending more money policing drugs, they increased funding of rehabilitation programs.
Health and healing instead of harm!
Policing drugs has been proven again and again to only increase the demand for, price of and crime around drugs. The research on decreasing drug misuse is overwhelmingly in favor of putting energy towards healing instead of punishing, but few governments have paid attention to this research.
These policies were put in place mainly because Portugal was leading Europe in deaths related to drug use and HIV. Decriminalization was complemented by the expansion of a welfare state which included resources put towards harm reduction, social reintegration and a guaranteed minimum income.
Studies I’ve read suggest that the wider health and social reforms in Portugal have helped the decriminalization policies to achieve the positive societal outcomes seen in the country today.
Of course Portugal is not perfect, but when I walk around Lisbon, I see a city (and country) that feels like it’s looking towards a future that is greater than its past.
Most of the time, I can’t fathom what it would look like to have leaders who have an imagination for a better world for the many instead of increasing the wealth of a handful of billionaires. But when I walk around Lisbon, I get a picture of what it could look like…
Independent bookstores on every corner.
Exquisite museums, including a gorgeous museum dedicated to the history of azulejos (Portuguese tiles) housed in an old convent.
The expansion and maintenance of affordable public transportation.
More spaces for tram lines than for cars.
Beautiful public spaces where people gather. Public squares and well-kept streets.
More than anything, I think being in Lisbon encourages imagination. It’s a space to dream. Maybe that is true of any beautiful city that is organized around human beings…I’ve definitely felt that way in Amsterdam watching bikes and in Paris as they have increased green space and bike lanes radically there in the last ten years.
But somehow it feels even more true to me that today, Lisbon is a place of possibility for dreamers.
And so after leaving a second time, I started to dream about bringing my whole family back there.
On New Year’s Eve in 2024, Taido and I were celebrating 30 years of marriage. It seemed like a great excuse to gather in Lisbon. I put the word out that all I wanted for my anniversary (and Christmas that year) was for my family – whoever wanted to – to join Taido and me in Lisbon.
I rented an apartment in the Alfama, the historic district east of the city center and invited everyone to make their requests about our time there together.
If I had to choose one theme for my third trip to Lisbon, it would have to be food, and maybe even specifically, coffee!
We wandered the beautiful streets together, but in between walks, we ate a lot. And we drank so much coffee.
We haunted old cafes like A Brasilieira and new ones from a list my son Ben made.
One of our favorites was the Copenhagen Coffee Lab, which has several locations around Lisbon.
In addition to coffee, they do brunch and matchas.
Almost every day, at least some of our group would make a stop in one of these coffee spots.
And we brought their bread back to the apartment by the loaf to have with soup and breakfast. In fact, for two months after this trip, I tested recipes until I had perfected my own version of their dark rye Danish bread, which I have been making ever since. It’s now a Chino House staple!
Between coffees, we visited several museums, wandered from one miradouro (hill top viewpoints) to the next and ate all the seafood!
When you’re a group of this size, someone is always hungry.
Often my only photo from a meal would be a pile of empty plates after we devoured every bite.
In addition to Taido and me, our Lisbon crew was our three of our kids (Ben, Mary Polly and Simon), my sister, and my niece and her partner who popped over from Dublin.
We ended up being in two apartments down the street from each other, but we would host meals and play cards at night in ours.
Early in the morning, Taido and Anna would go for a run as the sun came up along the river. Each day one or two kids would wake up to go with them. And sometimes I went and walked. We would get to where a lot of the clubs were located, and folks would still be lined up outside to get in at 7am. It amazed me every time.
Lisbon is definitely a city that doesn’t sleep, although the main squares were much quieter on those early morning walks. In the afternoons the same squares were packed with people.
We enjoyed being in Lisbon in time to catch some of the holiday vibe after Christmas.
I asked everyone later what their favorite things were about Lisbon, and again, the food was a recurring highlight. One group did a food tour that I booked but opted out of myself (since I’m a vegetarian) and they loved all the spots they hit on the tour.
When Ben got home, he recreated some Mozambican sandwiches they had that their guide told them was everyone’s hangover cure in Lisbon.
We also took the kids back to some of the places Anna and I had loved so much. Of course we went to Honest Greens, which we’d discovered first in Porto.
But some other favorites included Chapito a Mesa for seafood, Cantinho do Avillez for shared plates, and the rooftop bar at the top of Pollux for drinks with a view.
We made lots of meals at the apartment. We couldn’t believe the seafood offerings at the local supermarkets.
And we had pizza one day, because Anna and I had found a collection of divine restaurants inspired by Italy (and Portugal and Nepal!) on our first trip to Lisbon.
We had our anniversary dinner at Decadente, now called The Gandaia Club, which was divine!
And then we walked down to the river just before midnight to see the New Year’s Eve fireworks. It’s not often that I stay up until midnight on New Year’s Eve (also our anniversary), but being along the riverfront with the masses for the fireworks going off above the city AND out on the river was worth being out past my bedtime for sure.
Even though we had to bundle up a bit, it was so fun to be outside and often in the sun in January.
One evening some of us walked up to a sunset bar with books and cards to see the sun go down from above the city.
We warmed up every time we went uphill, which is often in Lisbon.
A lot of the days we would split up into smaller groups depending on who was interested in what, but one morning we all did a bike tour together that was so fun.
We rode along the river all the way to Belem, and our guide stopped along the way to tell us about different parts of the city.
We rode to the top of the architecture and technology museum, which the boys ended up coming back to the next day.
And we visited the LX Factory which is an old textile factory that has now been turned into a hub for artists, restaurants and shops.
We rode to have the Pasteis de Belem and again to the problematic Monument of the Discoveries, and then we rode all the way back. It was the longest I’ve biked in a little while and I definitely felt it.
I love doing a bike tour of a city, but then I’m glad to be back on my two feet again.
Walking the Lisbon city streets is how I spent my first hours there in 2023, and we ended our trip in 2025 doing much the same.
After a week in Lisbon, we had seen what we wanted to see, so we walked the Alfama neighborhood, had our favorite coffees one more time, and said goodbye.
Hopefully it’s not the last time I’ll be in Lisbon. I feel sure I’ll be back for another walk on the Rota Vicentina, but I don’t know that I’ll ever have a whole week in Lisbon again so I’m recording these memories now to treasure later.
I’m so grateful to everyone who came to Lisbon to help make my Lisbon family travel dreams come true.
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PS. If you go to Lisbon, please write and tell me how much you love it. And also, here’s my Lisbon Google map with all my saved spots, as well as a playlist for Wandering Lisboa.
Annnnd, if you enjoy my rambling posts about places I visit and walk, you can subscribe to get them straight to your inbox right here.
