This was published 7 years ago

Cities you need to travel to more than once to appreciate

By Ben Groundwater

Updated March 15, 2017 — 2.34pm

It's not always love at first sight when you're travelling. Some of the destinations that end up being all-time favourites won't necessarily impress you straight away.

Maybe they'll seem boring on that first visit. Or dangerous. Or lacking in character. The reality is that some cities are just better at hiding their charms than others, refusing to reveal them to casual visitors, forcing you to take another look if you really want to appreciate what they have to offer.

Once you get to know these places, you'll love them. But that first visit? Prepare to be unimpressed.

Finding little back alley restaurants is half the charm of Bangkok.Credit: iStock

Los Angeles, USA

From the window of the plane on that first approach, LA looks like a horrific urban sprawl, a true concrete jungle (although low-set, so maybe concrete scrubland). It's ugly. So you go to Hollywood, because that makes sense, but it's all rundown and charmless. You try to get to the beach, but there's no public transport and cabs are rare. LA, on that first visit, is a frustrating, confusing place. It's only after a few return trips that you discover Santa Monica, and Los Feliz, and the revitalised Downtown area, and the Sunset Strip, and realise that there's plenty about this city to love.

Roller skating at Venice Beach, Los Angeles.Credit: Alamy

Dubai, UAE

If you really enjoy gigantic resorts and flashy extravagance, endless shopping malls and big business, then maybe you'll have fun in Dubai the first time around. If, however, you like good, affordable Middle Eastern food, and boutique art galleries, and little drinking holes populated by a fun expat crowd, and being able to walk places, then it will take at least two or three stopovers in this booming megalopolis to discover its true charms.

See also: Why Dubai is worth a visit

The Palm Jumeirah in Dubai.Credit: iStock

Bangkok, Thailand

The obvious thing to do in Bangkok is to book a cheap hotel somewhere near Khao San Road and go live the dodgy backpacker dream. Only, it's kind of a nightmare, and the heat of the Thai capital, coupled with all of the scammers giving naïve travellers their best shot, will render your first visit to the city an unenjoyable one. It's only after spending a little longer exploring, checking out the street food hubs, finding little back-alley restaurants or fancy rooftop bars, and learning to deal with the scammers, that you'll begin to love Bangkok.

See also: 20 reasons to visit Bangkok

Bangkok's weekend Vespa market near Chatuchak.Credit: iStock

Naples, Italy

If you're hoping for the dream version of Italy, the fantasy that's contained in the canals of Venice and on the beaches of the Amalfi Coast, then you'll be disappointed by Naples. This is no one's fantasy. It's grimy, it's a little dangerous, and the attractions are nowhere near as obvious as they are in other parts of the country. Naples does, however, have a rough charm and a lived-in vitality that will slowly become apparent to anyone willing to give the city a second chance.

Typical neighborhood in Naples.Credit: iStock

Moscow, Russia

Moscow is the epitome of the big, bad city, all grey skies and towering Brutalist architecture, crowded streets and unsmiling faces. It takes a while to adjust to Moscow, to get accustomed to its ways and its rhythms – a few days isn't enough. Once you begin to get it, however, the romance of the Russian capital becomes clear. This is a city of writers and artists, dancers and philosophers, and it suddenly seems so full of culture instead of so devoid of charm.

Jakarta, Indonesia

Most people spend plenty of time during their first visit to Jakarta wondering what possessed them to book their first visit to Jakarta. None of the things that make Indonesia great seem to be here: no beautiful beaches, no smiling Balinese, no backpacker bars or good times. Just traffic; so much traffic. Just hustle and bustle and pollution and cars. But Jakarta can be fun if you give it a chance. It can be enjoyable if you know where to go. Just try to stay off the roads.

Dutch colonial facades of Jakarta.Credit: iStock

Santiago, Chile

When you arrive in South America excited for the romance of Buenos Aires, the edginess of Lima, the sex appeal of Rio de Janeiro, and the otherworldliness of La Paz, of course you're going to be disappointed with Santiago. The Chilean capital is just a city, devoid of big attractions, a little shabby and plain. But there's fun to be had here. There are great restaurants in the Lastarria neighbourhood, great bars in Bellavista, shopping in Vitacura, plus access to wineries, ski resorts, and the coastal fun of Valparaiso. It's worth revisiting.

See also: 20 reasons to visit Santiago

Toronto, Canada

Toronto is another city that suffers by comparison to its neighbours. When you're being held up against the likes of Montreal and Quebec City, of Vancouver and even Calgary – not to mention all of the amazing natural attractions in Canada that exist outside the urban hubs – it's easy for people to be disappointed. But Toronto will gradually charm you. It'll allow you to discover its multicultural neighbourhoods, its outdoor lifestyle (in the summer at least), its friendly locals and its great music scene. But only if you give it a second chance.