When I was in my twenties I used to ride the metro there with a good friend who was French, and she always was annoyed (“Why do you care?”) with my habit of choosing which car of the train to board so I’d be lined up with where I was going. I still do it, and I’d say honestly that it’s probably a marker of a certain type of obsessive personality which I now understand and confess to.
Like my friend, Mexico too is the opposite of that personality. A few nights ago I rode the metro back to our rental and across from me was a family, three generations riding together. A couple with what looked like the woman’s mother, and her two children. Her husband held an oversized girl (probably about five) in his arms as she slept and the mother read her other younger daughter from a paperback book. I almost stayed on the train past Tacuba (where I needed to transfer) just because I was enjoying watching them. If I really knew how to live slow I probably would have stayed on the train.
A couple of days ago I received a screed from a good friend asking “Why should it be more difficult to turn on a TV today than it was 50 years ago?” I think that’s a good question. I’ve spent several days trying to craft a workaround so I can import captions into the picture galleries on this blog, almost a complete waste of time since I never got it working. I still position myself on trains, and am still hyper-aware of timings that most people hardly pay attention to.
Sometimes it’s good to be in a place that’s just the opposite of who you are. I’d like to think I share some characteristics with the people in Mexico City – and that’s true – but there’s certainly a lot of foreign territory.
Sadly, I’m not still friends with the woman from my twenties. Her email address hides behind multiple layers of verification codes, and I’ve never been willing to jump through the hoops. But I actually would like to compare notes and see where she ended up too.
I feel it’s my compassionate duty to beam back warmth and color to my northern friends enduring the gnarly part of winter. As we took off from the Montreal airport the landscape was a frozen monochrome white. Beautiful, in a graphic way, once you got off the ground but still hard ice.
A friend from home has been reminding me almost daily of the countdown to changing our clocks, a small encouragement and marking of spring’s impending arrival. I hope some of these photos will work to warm you. Some are from previous visits to Mexico City, but they are all taken at this time of year, when the city breaking out into spring.
If you wanted to choose a city that’s diametrically opposed to Montreal’s cranky winters, Mexico City would be a good choice. The high altitude brings spring-like weather all year round, with warm days and cool nights. In February the mornings start at 12C warming to 20-25. Only pollution downgrades its perfect ranking.
As penance for posting the deep-of-winter photos last week, I offer these to warm you up, or at least make you feel better.
▲ Catania Fish Market The star of this market is the swordfish, but even the sardines are unusual. It’s true that plastic crates and digital scales abound, but still there’s a feeling of the market being enmeshed in long-running traditions, which gets reflected in the city’s approach to urban planning as well.
The Irresistible Pull of Gritty Cities: Understanding Why We Love What We’re Missing Part II
One of the most striking features of these older cities is their incredible diversity of housing types and price points, often within the same neighbourhood. In Damascus, you might find a restored 17th-century merchant’s house next to modest apartments that house working families, with both sharing the same narrow street and the same access to local amenities. Palermo’s neighbourhoods mix recently built condos (often retaining traditional facades) with affordable housing apartments, creating the kind of economic integration that many newer developments actively prevent. To give Montreal credit, some neighbourhoods share this diversity, but it’s often frowned on as “gentrification”.
▲ No problem with gentrification here This street was founded by Greek colonists in Agrigento, on the southern coast of Sicily, probably around 580 BCE. I would surmise that the Greeks used slaves to haul the blocks used in the construction.
This mixing isn’t just socially beneficial – to me it’s economically essential for urban vitality. It’s what helps create a local economy with non-chain, locally owned businesses. Diverse housing types create diverse local economies, supporting the small-scale entrepreneurship that makes a neighbourhood interesting and economically resilient.
The housing diversity in these cities also reflects their adaptability over time. Buildings that were constructed as grand single-family homes can be subdivided into apartments when economic conditions deteriorate, or combined back into larger units when gentrification pressures increase. We’re often critical of this, but it ‘s a flexibility built into the architectural DNA of older cities that allows them to respond to changing demographics and economic conditions without wholesale demolition and reconstruction.
▲ Even in ancient neighbourhoods like this one in the Sicilian hill town of Piazza Armerina you can differentiate the renovated houses by window style and roofing.
The Art of Adaptation and Resilience
Perhaps the most remarkable quality of these beloved gritty cities is their capacity to adapt and evolve while maintaining their essential character. They’ve survived empires, wars, economic collapses, and social upheavals not by standing still, but by continuously adapting their built environment to new needs while preserving the underlying urban logic that makes them work.
Damascus offers perhaps the most dramatic example of this adaptability. The old city has continuously evolved over millennia, with Roman columns supporting Islamic arches, Byzantine churches converted to mosques, Ottoman palaces repurposed as museums, and traditional courtyard houses transformed into restaurants and cultural centres. Each layer of history adds to rather than erases the previous ones, creating the rich texture that makes the city so compelling.
▲ Damascus is probably the best example of a living city, with Roman, Ottoman, and “contemporary” structures all sharing space in this photo.
The Integration That Creates Magic
What makes these cities truly special isn’t any single characteristic but how all these elements work together to create something greater than the sum of their parts. The human scale enables walkability, which supports diverse public spaces, which creates markets for diverse housing types, which generates the economic activity that supports adaptation and renewal. It’s a virtuous cycle that has been refined over centuries of urban living.
What We’re Missing at Home
Standing in my ordered, well-regulated neighbourhood in Montreal, I often think about what we’ve traded away in our pursuit of efficient, predictable urban environments. Our streets are wider and cleaner, our building codes more rigorous, our public spaces more carefully maintained. These aren’t bad things – they reflect genuine improvements in public health, safety, and accessibility.
▲ The Montreal Plateau is relatively flat as its name implies, with spikes of church spires and an occasional out-of-place apartment tower. The visually boring cookie-cutter buildings in the foreground enforce a visual style, but their predictability saps vitality.
But in our effort to eliminate the inefficiencies and unpredictabilities of older urban forms, we may have eliminated some of their essential vitality as well. Our zoning codes separate uses that these older cities mix naturally. Our building standards favor large-scale development over the small-scale, incremental growth that creates diverse, affordable neighbourhoods. Our traffic engineering prioritizes movement over lingering, getting through rather than being in.
▲ Exceding all predictions The Décarie autoroute as it was designed in the early 1960’s was supposed to max out at 90,000 cars per day. It now handles an average of almost double that.
The question isn’t whether we should abandon our standards and return to some romanticized past, but whether we can learn from what these older cities do well while maintaining the genuine improvements of contemporary urban planning. Montreal offers some lessons in this direction. The city’s pedestrianization of portions of Ste-Catherine Street shows how even established cities can evolve toward more human-centred design.
Living in the Tension
Perhaps what I’m really drawn to in these places isn’t their grittiness per se, but their willingness to live in productive tension between competing values. They’re not trying to optimize for a single goal but rather to balance multiple, sometimes contradictory objectives: old and new, local and global, efficient and experiential, ordered and spontaneous.
The cities I love aren’t perfect, and I certainly wouldn’t want to eliminate building codes or return to pre-modern public health standards. But they offer something that our more regulated urban environments often lack: they feel like places where humans have lived, adapted, and created something together over time. They feel like home not because they’re comfortable or convenient, but because they’re complex and alive.
The narrow streets of Damascus, the piazzas of Palermo, the pedestrian rhythms of Thessaloniki – these aren’t just tourist attractions or nostalgic throwbacks. They’re working examples of urban principles that we ignore at our peril. As cities around the world grapple with climate change, housing affordability, and social isolation, these older urban forms offer tested strategies for creating places that are not just efficient but truly livable. The question is whether we’re wise enough to learn from them.
▲ A couple in a Piaggio Ape, a vehicle nimble enough to navigate easily through town, and displaying the icons of their traditions. Piazza Armerina, Sicily.
The Damascus photograph in this post is taken from a book I’m just finishing (Return to Damascus: A Personal Journey) on the experience I had in returning to where my father had been born.
▲ Catania Open Market I envy the Sicilians and their abundant produce, even at the end of November. Their markets are noisy and colorful. The produce feels close to the farm, which it is.
The Irresistible Pull of Gritty Cities: Understanding Why We Love What We’re Missing
I’ve always found myself drawn to certain cities with an almost magnetic pull – places that feel lived-in, weathered, and wonderfully imperfect. From the narrow stone alleys of Damascus to the chaotic vitality of Mexico City, from Palermo’s winding streets to the crumbling decadence of Thessaloniki, these are cities that seem to embrace their contradictions. They’re places where modernity coexists awkwardly but beautifully with centuries of accumulated history, where every street corner tells multiple stories, and where the urban fabric feels genuinely human in scale.
▲ Thessaloniki Old City We drove our car through these streets and it was definitely a social experience, since traffic was both directions and each encounter was a negotiation. The stairs on the right definitely would not satisfy Montreal’s setback regulations.
As someone who calls Montreal home – a city that sits comfortably between order and character – I often wonder what it is about these grittier places that captivates me so deeply. Is it simply the allure of the tourist’s gaze, romanticizing what locals might find frustrating? Or is there something more fundamental about how these cities are designed and how they’ve evolved that creates genuinely superior urban experiences?
I believe it’s the latter. These cities embody qualities that many of our more regulated, sanitized urban environments have systematically designed out – and in doing so, we’ve lost something essential about what makes a city truly livable.
▲ Jean-Talon Market Montreal Our winter markets are abundant but everything is quite orderly, and (sadly!) imported from afar, especially when compared to Catania.
The Human Scale That We’ve Forgotten
Walk through the old quarters of Damascus or wander the residential streets of Palermo, and you’re immediately struck by how perfectly sized everything feels for human beings. Buildings rise to four or five stories – tall enough to create urban passageways but low enough that you can still make eye contact with someone leaning out a third-floor window. Streets are narrow enough that neighbours can converse across them but wide enough for the essential choreography of urban life: children playing, vendors selling, neighbours meeting, deliveries being made, life happening.
▲ Damascus Street Football Other than there not being any women in this photograph, a lot is happening on the street. This was in the Old City.
This isn’t accidental. It’s the result of centuries of organic development where buildings were constructed at the pace and scale that individual families and small communities could manage. In Thessaloniki, the traditional urban fabric prioritizes pedestrian comfort over vehicular efficiency. The narrow streets that might frustrate a traffic planner become perfect corridors for social interaction, where the pace naturally slows and encounters become inevitable.
▲ Palermo’s streets pick up on the city’s ancient layout, with automobiles present but taking a backseat.
Contrast this with our modern approach to urban development, where efficiency and standardization trump human experience. Even in Montreal, our newer developments tend towards what we define as modern experience – wider streets, taller buildings, larger blocks that prioritize movement over lingering. We’ve optimized for cars and commerce rather than for the casual encounters and spontaneous connections that actually make urban life rich.
▲ Looking north in Montreal from Côte-des-neiges at residential and commercial buildings in one of the fastest expanding parts of the city.
The smaller scale of these older cities creates what seems to me the conditions necessary for urban vitality. Even though they may look to be museum pieces, they aren’t. They are living examples of urban design that puts human experience first.
Public Spaces as the City’s Living Rooms
Perhaps nothing distinguishes these gritty, beloved cities more than the quality and accessibility of their public spaces. Not just parks or grand plazas, but the everyday spaces where public life unfolds: the stepped streets of Damascus that become impromptu gathering places, the piazzas of Palermo that serve as outdoor living rooms for entire neighbourhoods, the casual sidewalk life of Mexico City where sidewalks and public spaces encourage people to meet and relax”.
These cities understand something fundamental: public space isn’t just about recreation, it’s about democracy. It’s where different social classes, ages, and backgrounds encounter each other naturally. When public space works well, it becomes the foundation for social cohesion and civic engagement.
▲ Preparation for Women’s Day March International Women’s Day has been commemorated in Mexico City since the 1930s, but the massive street mobilizations began gaining momentum in more recent decades as a response to Mexico’s epidemic of gender-based violence.
Mexico City is often dismissed as sprawling and car-dependent, but alongside that reality I see a lot more going on. The city’s downtown areas have spacious parks and sidewalks, accommodating an unending ballet of commuters, tourists, and street vendors. On Sundays, major arteries like Paseo de la Reforma are closed to cars and opened to pedestrians and cyclists, temporarily transforming the large parts of the city into one enormous public space.
▲ Mexico City’s less romantic side The city government has tried different approaches at reducing car traffic, all with little success. Nevertheless, there is an inexpensive and well-used public transport system used by 14 million people a day. The open lane is a reverse direction lane for buses.
What these cities understand is that public space isn’t a luxury – it’s infrastructure. Just as essential as water pipes or electrical grids, public space is the network that allows urban society to function, providing the venues for the informal encounters and casual sociability that bind communities together.
Walkability as a Way of Life
In these cities, walking isn’t exercise or a lifestyle choice – it’s simply how you get around. This creates a fundamentally different relationship between residents and their urban environment. When you walk regularly, you notice things: the quality of surfaces, the presence or absence of shade, the rhythm of street life, the small businesses tucked into ground floors.
▲ Damascus Old City Bakery Man carries away hot bread purchased from a small bakery.
Thessaloniki, despite its challenges with broken pavements and sidewalks, illegally parked cars and motorcycles, kiosks and coffee tables, has a vibrant street culture. I look forward to going back soon to see how the city has adapted to its newly-opened metro system, which hopefully will reduce the perpetual gridlock many of its streets experience during the day. Hopefully the ongoing integration of walking and public transit has created an even more layered urban experience.
Mexico City exemplifies this integration beautifully. Despite its size and complexity, the city maintains an impressive pedestrian culture. Under the leadership of mayor Claudia Sheinbaum (who has a background in environmental engineering) the city dramatically expanded its network of public transit, bolstering its generous public spaces with wide sidewalks and creative public squares.
▲ Mexico City’s Metrobus System provides rapid transit with a two dedicated lane system. Multi-unit buses (some all electric) load in stations much like a metro line. Claudi Sheinbaum was instrumental in launching the system as Secretary of the Environment (2000-2006) under then-mayor Andrés Manuel López Obrador, who went on to be President, as she has too.
Next week: Housing. The Damascus photographs in this post are taken from a book I’m just finishing on an experience I had with my father, returning to where he was born.
