I admit it:  I’m a big planner.  Generally my detail orientation and organizational prowess are quite handy, even desired skills, and yet I’ve learned–both in planning my life and in planning trips–that sometimes you need to let go.  It’s not necessary to plan every single moment of your day.  While this may seem obvious to you, for those of you reading this who are just like me, you know what a revelation this is.

When I’m travelling, though, I am far more relaxed than I am at home and have always had an easier time giving myself up to the moment.  Yes, I do my destination research beforehand, and I do purchase the museum tickets and make a reservation or two before leaving home, but I also allow for flexibility and even whole chunks of free time.

And this is where Serendipity often seizes its opportunity.

One particular instance comes to mind.  Two years ago, on a trip to Florence, Italy, I was on a mission to buy leather boots.  As my partner, Ken, supported me in this effort, pointing out potential shops, we came upon a gelateria and decided to take a break and indulge ourselves for the second time that day.  We sat on the stone steps of (what else?) a cathedral while eating our cups of pistacchio and melone decadence when Ken nudged me and directed my attention toward an especially fine specimen of Italian manhood.  (It should be noted that Ken is very secure in our relationship!)

Aurelio looked to be George Clooney’s taller, better looking, younger brother.  Seductively slumped against a Vespa, smoking a cigarette as if he were whispering sweet nothings into its ear, wearing a blue sweater that was only almost as blue as the inviting sky of his eyes (I could tell even from a distance, so piercing were they!).

I licked my gelato.

(About now, you’re thinking, but what does this have to do with serendipity.  Be patient!)

Aurelio flicked his cigarette away and entered the leather shop he’d been loitering outside.  We finished our gelato and I said, “Maybe they have boots.”

No boots, but jackets, bags, and other objets d’leather and nothing, really, that I wanted to buy or could afford.  While I browsed, Ken struck up a conversation with Aurelio and we wound up chatting with him for about 45 minutes.  We even took his picture!

Aurelio and Me

When we were finally ready to leave, I had one last question for Aurelio.  Where does he eat in Florence?  Because we had been trying to find a restaurant frequented by locals, not tourists–not the easiest of undertakings in a city like Florence.

While he demured that he rarely eats out because his wife (drat!) is such an exemplary cook, he did give us a suggestion.  Not only did he provide us the name, but he drew us a map from our hotel to the restaurant and even told us what to order.

We followed his instructions and ordered what he told us (a good thing, since the menu had no English and our waiter wasn’t exactly bilingual) and it was hands-down the best meal we had in Florence, if not on our entire trip in Italy.

More than two years later, at the mere mention of the phrase bistecca fiorentina, I can taste the garlic and lemon and olive oil sizzling on my tongue, and everything about that magical night in Florence comes flooding back:  the warmth of the late September evening, the strings of lights dancing in the breeze, the desolate cobblestone street we strolled down, my shoes in my hand, the moon our only eyewitness.

For such Proustian memories as these can we thank Serendipity.