Solo on Santorini with romance in the air

"Lisa, you should go to Santorini with a boyfriend," one of my Greek relatives said while hosting me in the Athens suburbs for a few days before I left for a week in the islands.

"She will meet a Greek boyfriend!" her husband countered.

"Or an American one."

It was not my safety as a solo traveller that my hosts seemed to be concerned with, but my heart.

I interpreted their question as: How could you go to one of the world's most romantic spots on your own?

Perhaps. But I had always wanted to visit the Greek islands and I was done with waiting.

Santorini was on the top of my list and I was going.

In my 20s, I had spent most of my vacations visiting family and going to other people's weddings.

At 31, I needed an itinerary that was entirely my own.

All I wanted to do was traverse Santorini's dramatic calderas, relax on the beach and take in some extraordinary sunsets.

As far as companionship, Henry Miller's account of his travels in pre-war Greece would do just fine.

But on my second day on the island, I stumbled upon a bookstore run by a gaggle of Americans and Brits and promptly changed my mind about that no-romance pledge.

Bounding down the stairs into a subterranean shop with books stuffed in every nook and cranny, I locked eyes with a bearded man at the cash register. I smiled at him, but mostly to myself.

Oh, it is on, I thought.

I did not know if he was single, but I knew he looked like my type.

After dinner, I returned to the bookstore's patio to watch the sunset with a bottle of wine.

While sharing it with that bearded cashier, he asked if I had planned this vacation with someone else, as if I had been tragically marooned with a honeymoon suite all to myself.

"No, I planned to come here alone," I said, noting that it had been a rough couple of years, romantically.

A lot of promising starts, but nothing lasting. The least I could do was to take myself on a getaway, never mind that I was surrounded by lovers and families.

Over the next few days, I tagged along with him and the rest of the bookstore crew.

I joined them for a twilight swim and a home-cooked meal on a neighbouring island one night, and that bearded cashier invited me out for a one-on-one dinner the next.

He was, in fact, single and we were hitting it off.

Back in my real life in Washington, DC, the men I usually dated ranged from boring lawyers to interesting-yet-flailing creative types.

There was no one who had done something as sexy and risky as opening a bookstore in a foreign country.

During our date, we talked more about our lives: mine in Washington, which I often found lacking in the love department, especially as 20somethings moved in and out of town so often.

Rarely did I meet someone looking for something real right when I was.

And he talked about how lonely it could get, living in a place where everyone else was perpetually on holiday.

He proceeded to fantasise about what a relationship between us might be like, joking about reserving a ticket to Dulles International Airport and all that might entail.

Clearly, this was a man who made his living selling fiction, yet I took in every word.

And why not? What is a vacation if not a break from reality?

Every good trip, no matter the traveller's relationship status, entails some kind of romance.

Not necessarily with a person, but with the question: What would life be like if we ditched our life back home and stayed?

Here was someone who had done just that and I found it incredibly intriguing.

Like me, he was surrounded by honeymooners - not for a week but all year round.

Suddenly, my own solo trip here made more sense.

I also realised that dating on vacation, while seemingly pointless, was actually liberating.

In DC, my dates often felt forced and rote - as if we were auditioning one another for a life together.

Now here I was, enjoying myself with someone I had stumbled upon and connected with, rather than selected from a crowd of online-dating profiles.

That serendipity, plus the knowledge that a vacation fling would not go anywhere lasting, resulted in that rare date where the pressure was off and the romance was on.

Later that night, after a climb through an old castle and more carousing with customers at the bookstore, he told me to hang on to our time together, saying: "When you're back in your real life, whenever you're sad, just know that I'm a little bit in love with you."

I did not say it back, but I was too.

When we said goodbye the next morning, he told me to write to him and come find him some day.

A few weeks later, I did send him a handwritten note... and never heard back.

Nonetheless, our fling seemed to hold me back in my real life.

I would think: "What, you don't own a bookstore on a Greek island? How ordinary."

Eventually, I did move on and let the memories just be.

Three years later, when a mutual friend was visiting Santorini, bookstore guy and I hopped on FaceTime together. His fantasies about our relationship were alive as ever.

This time, though, I told him to stop with the storytelling.

Now, whenever I am worn out or underwhelmed by the DC dating scene, instead of thinking of him, I occasionally think back to that trip as a symbol of romantic possibility.

At any moment, my luck might change. There really are a world of options out there.


A version of this article appeared in the print edition of The Sunday Times on June 25, 2017, with the headline 'Solo on Santorini with romance in the air'. Print Edition | Subscribe