Tbilisi is not the kind of city that politely introduces itself. It rushes at you all at once — a jumble of medieval alleys, baroque balconies hanging by a miracle, Soviet boulevards, and glass bridges that look as if they landed here from another galaxy. For an urban planner, walking through the Georgian capital is like speed-dating with every planning doctrine of the last five centuries. Some encounters are charming, some awkward, and some you’d rather forget.
Take the Old Town. Wooden verandas lean over cobblestones at angles that would make any structural engineer sweat. Families sip wine in shady courtyards while tourists snap pictures of laundry flapping above their heads. It’s picturesque, yes, but also precarious. Earthquakes, humidity, and speculative developers all eye these fragile houses with different plans. And yet, somehow, against all odds, much of it still survives — a living reminder that heritage can thrive if locals keep using it instead of embalming it.

Then came the wild years of deregulation in the 2000s, when Tbilisi decided that urban planning was overrated and that free-for-all construction might be more fun. And fun it certainly was — for investors and architects with an appetite for spectacle. Suddenly, there was the Peace Bridge, gleaming like a giant pair of sunglasses across the river. Next came glass police stations, tube-shaped concert halls, and towers that seemed to have been ordered from an international catalogue of “Things Cities Buy When They Want to Look Modern.” It was exhilarating, chaotic, and occasionally ridiculous. Imagine SimCity played by someone who keeps hitting the “random building” button.

Of course, the bill came due. Green spaces shrank, traffic multiplied, and the skyline began to resemble a family photo where no one knew there was a dress code. Yet amid the chaos, some of these experiments worked. The Peace Bridge, once ridiculed, is now one of the city’s best-loved landmarks. The point, perhaps, is that Tbilisi has a talent for embracing the absurd until it somehow feels authentic.

Up the slopes above the river, a new Tbilisi is taking shape. Hillsides that once framed the city like a natural amphitheatre are now sprouting terraces of concrete and glass. Developers promise “living above the city” with postcard views of the old town and the Caucasus beyond. And it’s true — the sunsets are spectacular — but so are the questions: how do you get a school bus up a road that feels like a ski run, and what happens when the hillside decides it prefers sliding down to holding still? From afar, the new neighbourhoods look like a daring experiment in vertical living; up close, they feel more like a tug-of-war between ambition and gravity.
Meanwhile, everyday life goes on in ways that defy official planning. After the Soviet Union collapsed, many residents built their own solutions: glassed-in balconies, rooftop sheds, stairwell kiosks. From above, apartment blocks sprouted like wild plants. From below, they looked like stubborn declarations of survival. To outsiders, these add-ons can seem messy; to locals, they were necessary. And in a way, they reveal a truth planners often forget: cities are not made only by regulations and masterplans, but by ordinary people hammering together what they need.

Transport, naturally, is another battlefield. The narrow valley funnels cars into endless traffic jams. For decades the solution was: build more roads, widen boulevards, let the marshrutkas (minibuses) buzz around like caffeinated bees. The result? A city where honking sometimes feels like the official soundtrack. Lately, though, Tbilisi has started to rediscover public transport, bus lanes, and even bike paths. Progress is slow, but the mere sight of a new bus fleet is enough to make locals feel like something is finally moving in the right direction — besides cars stuck in gridlock.
And this is perhaps the most endearing thing about Tbilisi: it is gloriously imperfect, forever caught between the urge to preserve its fragile past and the temptation to chase glittering futures. Some cities try to iron out their contradictions. Tbilisi flaunts them. It’s chaotic, beautiful, frustrating, and inspiring — often all at the same time. For planners, it’s a warning and a delight: a city that proves urban life is not a tidy blueprint but a messy experiment, improvised daily, with a glass of wine waiting at the end of it.