It is an old cliche that travel broadens the mind. But what happens when the cities one visits become familiar favourites?

I thought about this recently when I visited London's National Gallery. Since I discovered its marvellous art collection on my first visit to London two decades ago, the Gallery has been my must-see whenever I am in the city.

I used to make a beeline for a particular gallery, where two of my favourite Titian paintings were hung side by side. I still remember the joy of stumbling onto the display on my first trip and spending 30 minutes in front of Bacchus And Ariadne and The Death Of Actaeon, just drinking in their beauty. A pilgrimage to that room has been an integral part of my London trips since that encounter.

Then four years ago, I discovered to my dismay that the galleries had been rearranged chronologically, and the early and late Titians were now separated, in different galleries. It's not the same, I grumbled to my friends, because the dynamic of seeing the works side by side is lost.

Yes, very #grumpyauntie. Which made me consider in turn how the way I travel has changed over the years.

In my 20s, it was all about the glamour and thrill of new destinations, the challenge of navigating new cities and the triumph of surviving solo expeditions into the unknown.

I felt very grown-up at 25, for example, when I survived a solo trip to New York at a time when the city's image was that of a crime-ridden urban ghetto - horrified friends thought I would get mugged or worse. Instead, I discovered the Temple Of Dendur in the Metropolitan Museum of Art, spent a fruitful day at Strand Book Store and fulfilled one item on my bucket list when I went to the jazz icon that is the Village Vanguard.

New York was a cakewalk compared with the crazy maze that was Moscow, with its different language, Cyrillic alphabet and casually erroneous and/or missing signage that made navigating in the pre-Google Maps era a challenge of 18th-century proportions. The difficulties made the tiny victories - finally finding the Novodevichy Convent and Izmailovsky Market - sweeter.

Visiting Beijing in 1998 presented a different sort of challenge, when I was confronted with the cultural chasm that separated me from the mainland Chinese. I found to my dismay that most of the Chinese service staff paid attention to me only if I made a fuss in English. A Chinese face, I learnt, was presumed local and therefore not worth any attention. I found it rather depressing and draining to have to be so aggressive all the time and have never visited the city again.

These trips were as much about self-discovery as about discovering new destinations. I learnt that nervous as I was, removed from the safety and efficiency of Singapore systems, I could manage.

As philosopher Albert Camus famously declared in his essay, Love Of Life: "For what gives value to travel is fear." Travel, he observed, takes people from the refuge of routine, "which protect us so well from the pain of being alone".

Contrary to his latter observation, however, I've discovered that travelling alone can be a pleasure, just as travelling with family and friends can be a real pain. On my own, I can spend a whole afternoon browsing in a bookshop or sit quietly in front of a work of art for 30 minutes with no one to hustle me.

But I've also come to appreciate, as I grow older, that good travel companions are one of the truest boons in life. Travelling together is a surefire way of testing friendships. You see people's true mettle when they have to cope with the unexpected, deal with delays and share a hotel bathroom.

There is also an inestimable joy when you build a storehouse of shared experiences together.

As I settle into my 40s, travel has evolved for me - from a constant hunt for the new to a comfortable return to the familiar. While I do make it a point to discover new nooks and crannies in cities I love, I also find myself revisiting my favourite spots.

In Tokyo, it is the Ghibli Museum, Blue Note jazz venue, Isetan's food basement and other assorted favourite eateries. In New York, it is The Frick Collection and the Metropolitan Museum of Art. In London, it is the bookshop Hatchards, the Tate Modern and, of course, the National Gallery.

Over the years, these venues have accumulated little "memory flags", as writer Jan Struther's Mrs Miniver says of a familiar landscape that blooms with fond associations. So my little memory flags planted in the various cities remind me of happy encounters over food and art. These treasured slivers give a place more emotion and texture, drawing me back on subsequent trips.

But the changes in the way I travel now are also influenced by technology. I used to sally forth in new cities armed with a Dorling Kindersley guidebook and printed maps. I would study these meticulously and memorise routes so as not to look like a gauche tourist (i.e. prime mugging target) at street corners with an unfurled map.

Nowadays, equipped with Google Maps, TripAdvisor, Foursquare and Yelp as well as a good data plan, it is easy to discover the "hidden" treasures of a city. On this London trip, I have been introduced to "insider" eateries by London-based Singaporean friends, only to find fellow Singaporeans occupying neighbouring tables. That Singaporean accent is at once comforting (Hey, fellow countrymen!) and comical (Oh no! Singaporeans!). We are a well-travelled bunch, citizens from this little red dot.

In this social-media age, it is easy to travel like a native. And I wonder if something is lost in the process.

The romantic view of travel, as expressed by Harvard philosopher George Santayana in his essay The Philosophy Of Travel, is "to escape into open solitudes, into aimlessness, into the moral holiday of running some pure hazard, in order to sharpen the edge of life, to taste hardship, and to be compelled to work desperately for a moment at no matter what".

I am not, nor will I ever be, the adventurous backpacker type who goes haring off into the wilderness. And working desperately for a moment seems too much like actual work, which is what I travel to escape from.

Liberation and renewal, I think, is what I seek in travel. Liberation from a workaday routine, and mental and spiritual renewal as I can dedicate the time to the theatre and museums.

The words "travail" and "travel" share etymological roots in the old French word for toil and an arduous journey. And from that root grows a philosophy to journey by: Forget the travail, and happy travels.