Travelling without a plan: How I came to like, if not quite love, Sydney

I've never found a thrill that I was looking for. They always seem to pop up by accident, unexpectedly. That goes double for the past week, which I spent in Sydney, Australia. For most of my life, ever since the first time I heard Men at Work's "Down Under" in 1984 -- I've been dying to go. Maybe I was expecting too much. Love at first sight is rare indeed, with people and with cities. Although my greatest love of all (I'll always heart you, London!) hit me like a thunderbolt, it took me a full week to fall for Buenos Aires's charms.

I rarely travel with an agenda, any set game plan. I prefer to experience a city the way the locals do and leave all those unforgettable travel experiences, the stories still worth telling 10 years later, entirely up to chance. As I write, I'm newly arrived in Melbourne and torn between what I should be doing (seeing the sights) and what I want to be doing (writing this post). "So what do you have planned in Melbourne?" my friend Andy asked me several times before I left Sydney. It's a reasonable question, but one I didn't have, or want, an answer for. Isn't planning a trip to the other side of the world difficult enough without having to account for the hour-by-hour particulars?

For me, yes. "I need a vacation from my vacation," I've heard people say countless times. No wonder. They try to pack so much activity into what's supposed to be quality rest-and-relaxation time that holidays become more stressful than a 9-to-5 job. My vacation motto: I'll know what I'm going to do when I'm doing it.

For Sydney, however, I went against my own golden rule and opted for several introductory days of sightseeing. The first thing that struck me about the city was how much it reminded me of so many others: Boston here. Washington D.C. there. A little bit of Chicago. A touch of Toronto. A dab of New York City. Even a taste of Istanbul (thanks to the hills-and-water combo).

Oh, yes, the hills. I wasn't expecting such a curvy walking experience. The views were lovely, if not quite breath-taking, and the people were ridiculously friendly. The only thing missing was something that was uniquely Sydney, something (aside from the Opera House) that wouldn't make me think of any other place. I was glad to be there, but it wasn't exactly the ultimate fulfillment of a life-long dream.

Andy told me that Sydney is a city best experienced in summer. That's when the outdoors scene -- the sun, the heat, bbq's, swimming pools -- takes over. It struck me as a ringing endorsement that could apply to any number of cities, including the one I live in! But I understood where he was coming from. Every time I've ever fallen for a city, I've been doing something that I could be doing anywhere when suddenly, I realize, Wow, I love this place!

For me, this serendipitous moment arrived on the morning of my sixth day in Sydney, during a grueling eighth-floor workout at Fitness First gym in King's Cross. I looked out the window, surveyed the scenery, and there it was: The Sydney Opera House. I'd gone there twice before and had been disappointed both times. Not only is it not as white as it appears in photos (see the photo above, from my second trip), but it looks like it could use a good scrubbing. This morning, though, standing majestically in the distance below, it was everything I'd always wanted and expected it to be. I sighed and took it all in. Finally, Sydney had given me something special, something specifically Sydney, to remember. And I wasn't even looking for it.