From Florence brilliance to Seville chaos, here’s what 53 walking tours taught us, and why we built a flexible, story-first way to explore on your terms.
You don’t do 53 walking tours without collecting a few great stories, a few hard lessons, and at least one moment where you think, why am I standing in a crowd staring at a wall while someone argues about tipping?
We’ve always loved the concept. A walking tour can snap a city into focus in the first hour, like adjusting the lens on your camera. That’s exactly why a guided tour app ended up on our minds long before we ever built one: we were chasing that feeling of walking past an ordinary doorway and suddenly realising it’s where something genuinely wild once happened.
When a tour is good, it’s ridiculously good. You start noticing the small stuff: the worn dip in a stone step where thousands of feet have passed, the way a laneway changes temperature in the shade, the half-hidden symbols above a shopfront that you’d never clock if you were just marching to a “must-see” list.
The best guides don’t just recite dates, they give you a plot. You find yourself following people, scandals, power plays, love stories, revolutions, and the kind of petty rivalries that make history feel very human. You leave with context for the photos you took, and that smug little joy of knowing the story behind what everyone else just walked past.
Then there’s the other side of city walking tours: the logistics.
Sometimes the only slot is right in the middle of the day you planned for a long lunch, a museum, or simply sitting in a square doing absolutely nothing, which is a deeply underrated holiday activity. Other times it’s “free”, except it’s not really free, because the tip conversation arrives early, returns often, and concludes with the emotional intensity of a final bill.
And guides are human, which means you get the full range. Some are brilliant storytellers who could make a cobblestone sound interesting. Others appear to be powering themselves purely on caffeine and vague resentment. After enough tours, you start thinking: there has to be a way to keep the storytelling and lose the scheduling stress. That’s the seed of a guided tour app, whether you call it that or not.
Florence is where we felt the “this is how it should work” moment. The city has that particular hum, scooters whining in the distance, footsteps echoing in narrow streets, the occasional waft of espresso and leather. The tour we joined wasn’t just a route, it was a narrative. Each stop connected to the next like chapters in a book, and you could feel the Renaissance stitched into the streets rather than displayed behind glass.
That experience quietly shaped the way we thought tours should feel: story-led, paced like a good conversation, and built around the people and moments that made a place what it is.
Seville gave us the opposite lesson.
We turned up hopeful, ready for layered history and local colour. What we got was… unpredictable. Our guide seemed to be wrestling a post-fair headache, the kind you can practically hear behind the sunglasses. An innocent question about flamenco swerved into an impromptu dance demonstration on the street. It was entertaining, absolutely, but it also derailed the whole flow. The tour ended early, the group looked around blinking like we’d been released from an accidental performance art piece, and we were left thinking: that’s it?
It’s a funny memory now, but it highlighted a real problem with traditional tours. Your experience can hinge entirely on someone else’s energy, timing, and professionalism.
The bigger frustration wasn’t even the awkward tours. It was the absence of tours altogether.
In parts of Umbria, for example, you quickly realise how many rich, layered stories sit in towns that don’t have the tourist-machine infrastructure. These places can be every bit as beautiful as their famous neighbours, sometimes with better food and fewer queues, but finding a decent walking tour can be oddly difficult. And that’s a shame, because smaller places often have the most surprising history, the kind that makes you stop mid-walk and say, wait, that happened here?
That gap, the places with plenty of story but no easy way to access it, became a major reason we leaned into building something more flexible than the standard group model.
After enough “wrong day, sold out” moments, enough overstuffed groups, and enough tours that depended on the luck of the guide draw, the shape of the solution became obvious. We wanted the best part of a walking tour, the storytelling, the sense of place, the little discoveries, without having to structure a whole day around someone else’s timetable.
That’s where MyGuideGuru began, as a guided tour app designed to give you that narrative thread while still letting you wander at your own pace. It’s also why we care so much about the delivery, because audio in your headphones can feel surprisingly intimate when it’s done right, like someone walking beside you pointing things out that you’d never notice alone.
If you’re curious about the thinking behind the tech side, you might like reading How an AI audio guide app builds a personalised tour in minutes. And if your heart belongs to quieter streets and lesser-known towns, Is Anywhere Really Off the Beaten Path Anymore? is very much your vibe.
We’ll always have a soft spot for classic walking tours, even the brilliantly awkward ones. They’re how we learned what travellers actually want: stories with texture, freedom to pause when something grabs you, and the ability to explore without a timetable breathing down your neck.
If that sounds like your kind of travel, MyGuideGuru is built for exactly that. Download the app, pick a place, choose a theme, and let the city tell you its secrets as you go, no crowds required.
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