The thing about serendipity, which is obvious but stay with me here, is that you cannot predict it. If you are a control freak, and some of us may be, this is quite maddening. It means that I had no idea when I went to a party and bought £10 of raffle tickets for a good cause that I was, in fact, picking my next holiday.

I couldn't quite believe that I had won anything, much less the grand prize, but, eventually, I ventured up to receive... an A4 manila envelope.

In it was a picture of a view of the sea from an apartment in a place called Cupra Alta. It seemed fabulous in every way, except one: it was in Italy. This would be a cause of rejoicing for most people, I know, but I had never really been on holiday in Italy and I suspected that, though it was undoubtedly nice, it was also full of Italians who would be speaking, yes, Italian.

The truth is that my holidays had become a little predictable - my only destinations being America and France - and I must admit that I rather liked it that way. I wanted a holiday like an old slipper, not a dangerously teetering stiletto. And the inescapable fact about Cupra Alta, a tiny hilltop village in the Le Marche region, is that it's very Italian indeed.

I considered not going but that seemed ridiculous. The only thing I know about random luck is that only a fool flouts it. Fairy godmothers are not to be trifled with. So we booked our flight to Ancona and headed out. On arrival, I was still somewhat surprised to find everything quite so Italian: the car-hire staff who spoke no English, the road signs, the drivers, the toll-booths. It seemed a triumph to get to the flat.

The learning curve was as steep as the Z-bends leading up to the apartment. It seemed that this bit of Le Marche (pronounced Markay) really is unspoilt. The tourists it caters for are Italian. In the tiny ancient hilltop villages we visited daily, we met only one other English tourist all week. Shop and restaurant opening days and times remained an utter mystery.

Ludicrously my partner and I had come armed only with a “Key Phrases Bookmark” and an ancient phrasebook. The first night, on visiting the local fish restaurant, none of the words on the menu matched any of the words in the phrasebook. We started pointing at other people's plates. The waitress looked alarmed when I whipped out the bookmark and tried to read from it.

The local café, in nearby Cupra Marittima, got used to the bookmark, and us. It's a good thing the Italians are so genuinely warm and relaxed. In France, we probably would have been barred. The high point came one morning when I ordered “tea with lemon” and the owner brought us plates of freebie crisps and tiny sarnies, a bottle of tonic and a glass full of clear liquid that turned out be a generous helping of gin.

Maybe it was the gin, but after a while I gave up caring that we looked fools. Soon nothing fazed us and the whole experience turned out to be energising, interesting and, most of all, fun. From now on, I'm going somewhere new every year. It would be nice if serendipity could pick the destination but, irritatingly, that is hard to arrange.

Ann Treneman is The Times parliamentary sketch writer

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