10 Best Cities in the World to Get Lost In: The Anti-Itinerary

From London’s hidden alleyways and Venice’s winding canals to Tokyo’s bustling backstreets and New Orleans’ historic French Quarter, discover 10 of the best cities in the world to get lost in, where unexpected detours, secret neighbourhoods and spontaneous discoveries make for unforgettable travel experiences.

Some of my most memorable travel experiences have had absolutely nothing to do with the itinerary. As a travel writer, I’ve travelled across continents, checked into extraordinary hotels, lingered over unforgettable meals and wandered through some of the world’s finest museums. Yet, when I think back on my travels, two rather less glamorous adventures come to mind. Both involved getting spectacularly lost.

The first was at London’s Bank station. Despite having visited the city more times than I can count, I found myself hopelessly disoriented in its labyrinth of underground passages, trying to work out which of its 12 exits would lead me to a friend waiting at a nearby pub. Then there was New Orleans, where a friend and I spent an afternoon going round in circles through the French Quarter, determined to track down a particular voodoo shop and the famed Faulkner House Books. Somewhere between the cobbled streets, colourful storefronts and our increasingly questionable sense of direction, the search became an adventure in itself.

Perhaps the most rewarding way to discover a city is to abandon the very thing that brought you there: your itinerary.

There is a particular pleasure in wandering without a destination. A wrong turn might lead to a tucked-away café, a neighbourhood you would otherwise have overlooked or an unexpected conversation with a local. It is often in these unplanned moments that a city reveals its true character, far removed from its celebrated landmarks and carefully curated tourist trails.

Of course, there is an art to getting lost. The trick is to do it deliberately, with time to spare, comfortable shoes and just enough battery on your phone to find your way back.

So turn off Google Maps, forget the must-see list and embrace the occasional wrong turn. From winding medieval lanes to wonderfully chaotic neighbourhoods, here are 10 cities where getting lost might just be the best part of the journey.

London

London is a city where getting lost is remarkably easy, whether you’re navigating the sprawling King’s Cross and St Pancras stations, trying to find the right exit from the labyrinthine Bank and Monument station complex, or wandering through the vast green expanses of Hyde Park and Regent’s Park. Yet London is a city best discovered above ground. It’s tempting to hop on the Tube and emerge at the next landmark, but doing so means missing much of what makes the British capital so captivating. Wander without a destination and you might stumble upon a secluded garden, an elegant Georgian square, a centuries-old pub or an independent bookshop tucked away on a cobbled lane. From the hidden courtyards of Mayfair and atmospheric backstreets of Covent Garden to the colourful mews of Notting Hill, leafy paths of Hampstead Heath and historic alleyways of the City of London, the capital rewards those willing to take the long way around.

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Fez, Morocco

Having visited Fez recently, I discovered just how easy it is to lose yourself in its extraordinary medina, one of the world’s largest and most intricate urban labyrinths. Unlike cities laid out on a grid, Fez evolved organically over centuries, its winding lanes shaped by climate, commerce, privacy and neighbourhood life. Narrow alleyways offer respite from the Moroccan sun, while traditional houses conceal tranquil courtyards behind unassuming doorways. Entire streets are devoted to centuries-old crafts, from leather tanning to intricate metalwork. Historically, this maze-like layout also made the medina difficult for outsiders to navigate, while locals knew every twist and turn. Here, getting lost is almost inevitable—and entirely part of the experience.

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Venice, Italy

Few cities make getting lost quite as enchanting as Venice. A maze of narrow alleyways, arched bridges and secluded campi (squares), the city was built around its canals rather than conventional streets. Follow a winding passage and you might emerge at a magnificent church, stumble upon a tiny neighbourhood trattoria or find yourself at a dead end overlooking a canal. Forget street names; Venetians navigate by bridges, churches and familiar landmarks. Here, boats deliver everything from groceries to furniture, waterbuses replace city buses, and daily life moves to the rhythm of the tides. Beyond the crowds of St Mark’s Square and the Rialto Bridge, Venice reveals its quieter, more intimate side to those willing to wander without a destination.

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Hong Kong

In Hong Kong, getting lost is a multi-level adventure. A city that rises as dramatically as it sprawls, its steep hills and soaring skyscrapers have created an extraordinary network of elevated walkways, escalators, underground passages and interconnected shopping malls. In Central and Admiralty, you can wander between office towers and shopping centres without ever setting foot on the street. Take the wrong escalator or exit and you might find yourself in an entirely different world, from the gleaming boutiques of Central to the bustling wet markets and traditional shops tucked away in its backstreets. Follow the Mid-Levels Escalator past lively bars, hidden cafés and neighbourhood restaurants, or head down to the waterfront, where ferries crisscross Victoria Harbour. In Hong Kong, the secret to exploring is to look up, look down and occasionally forget which floor you’re on.

Istanbul, Turkey

Istanbul rewards those willing to venture beyond its celebrated landmarks and bustling bazaars. Leave the tourist crowds of Sultanahmet behind and wander into neighbourhoods where traditional tea houses, colourful markets and quiet residential streets offer a glimpse of everyday life. Explore the cobbled lanes of Balat, the bohemian cafés of Cihangir and the steep backstreets of Galata, where every wrong turn promises another discovery. The city’s famously hilly terrain may leave you breathless, but the reward is often a spectacular, unexpected view of the Bosphorus, its passing ferries and minaret-studded skyline. In Istanbul, getting lost is as much a workout as it is an adventure.

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Tokyo, Japan

Tokyo is a city where getting lost can lead to the most unexpected discoveries. Beyond the neon-lit streets of Shinjuku and the famous scramble crossing in Shibuya lies a fascinating maze of narrow lanes, hidden shrines, tiny ramen bars and family-run shops. Even finding your way out of a railway station can be an adventure, with sprawling underground passages, interconnected department stores and dozens of exits. Wander through the nostalgic backstreets of Yanaka, the fashionable lanes of Daikanyama or the atmospheric alleyways of Golden Gai, where intimate bars are tucked into the most unlikely corners. Away from the city’s futuristic skyline, traditional bathhouses, neighbourhood shrines and handwritten menus offer glimpses of everyday Japanese life. In Tokyo, the most memorable discoveries often lie a few streets beyond the familiar.

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Boston, Massachusetts

Boston is a city where history has a habit of leading you astray. Unlike many of America’s neatly gridded cities, its winding streets evolved over centuries, with some following old colonial routes and others seemingly heading nowhere. Lose yourself in the cobblestone lanes of Beacon Hill, where gas lamps, red-brick townhouses and hidden courtyards evoke another era. Wander through the narrow streets of the North End, Boston’s Little Italy, where family-run trattorias, historic churches and irresistible cannoli shops await around unexpected corners. Follow the Freedom Trail, or discover the quiet squares, independent bookshops and waterfront passages that make Boston such a pleasure to explore on foot.

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New Orleans, Louisiana

New Orleans is a city where getting lost is half the fun. The historic French Quarter, with its network of one-way streets, confusing intersections and corners that look remarkably similar at every turn, can disorient even seasoned travellers. Beyond the jazz clubs and lively bars of Bourbon Street lies a maze of wrought-iron balconies, hidden courtyards and centuries-old Creole townhouses. Wander down Royal Street, with its antique shops, art galleries and street musicians, or take an unexpected turn into a quiet residential lane where the city’s old-world charm comes alive. Seek out Faulkner House Books, tucked away in Pirate’s Alley, explore the intriguing voodoo shops or follow the sound of drifting from a club on Frenchmen Street. In New Orleans, every detour comes with a little history, a little mystery and perhaps a Sazerac or two.

Canberra, Australia

Canberra’s sweeping boulevards, circular roads and seemingly endless roundabouts can turn even a short drive into an exercise in navigation. But beyond its meticulously planned avenues and monumental government buildings lies a city worth exploring without an itinerary. Venture into the neighbourhoods of Braddon, Kingston and Manuka, where independent cafés, acclaimed restaurants, boutique shops and lively weekend markets reveal a more intimate side of the Australian capital. Or head towards the bushland trails of Mount Ainslie and Black Mountain, where panoramic views of the city reward the occasional wrong turn. In Canberra, the real discoveries often begin where the grand boulevards end.

Paris, France

Paris is a city made for getting beautifully lost. Its 20 spiralling arrondissements, winding boulevards and labyrinth of historic side streets can confound even seasoned visitors. Venture beyond the grand avenues and familiar landmarks into the cobbled lanes of Le Marais, the hidden courtyards of Saint-Germain-des-Prés and the steep, village-like streets of Montmartre, where independent boutiques, neighbourhood boulangeries and intimate wine bars invite spontaneous detours. Cross the Seine to discover the quieter corners of the Latin Quarter, or wander through the covered passages of the Grands Boulevards, with their vintage bookshops and charming cafés. In Paris, the pleasure lies not in finding your way, but in discovering what you weren’t looking for.

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Rome, Italy

Rome is a city where getting lost feels like travelling through centuries of history. While its historic centre is relatively easy to explore on foot, the labyrinth of ancient streets, winding alleyways and unexpected piazzas can quickly lead you off course. Beyond the Colosseum and the Trevi Fountain, wander through the cobbled lanes of Trastevere, the atmospheric streets of Monti and the hidden courtyards surrounding Campo de’ Fiori, where ivy-covered façades, neighbourhood trattorias and artisan workshops reveal a more intimate side of the Eternal City. Follow a narrow passage and you might emerge at a magnificent Baroque fountain, stumble upon a centuries-old church or discover a tiny café tucked away from the crowds. In Rome, every wrong turn has the potential to become a journey through history.

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Perhaps the greatest pleasure of travel lies in discovering a city without following a prescribed route. The anti-itinerary isn’t about abandoning plans altogether, but leaving enough room for spontaneity, curiosity and the occasional wrong turn. Learn a few local phrases, embrace unfamiliar customs, strike up conversations and linger wherever something catches your eye. Keep Google Maps handy, but resist the temptation to consult it at every intersection. After all, years later, you may forget the landmarks you ticked off your list, but you’ll remember the hidden café you stumbled upon, the stranger who pointed you in the right direction and the afternoon when getting lost became the highlight of your journey.

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