The Real Santorini

The true story behind "Santorini Solo Travel: Surviving Greece's Romantic Island." In the fiction, a newly divorced man named Jeff takes the second-honeymoon trip he'd booked before his wife left and goes to Santorini alone, trying to survive an island built entirely for couples. I could write Jeff because I'd been Jeff, the lone backpacker among the honeymooners, doing the math on the nearest volcano. And then, years later, I came back as the other kind of traveler entirely.

How I Knew the Feeling

Here's the confession that makes the whole story honest: I didn't invent Jeff's loneliness. I'd field-tested it.

The warm-up was Lake Como. I went solo, flew into Turin, took the train up, and spent a few days as the only person in the most romantic lake town in Italy wearing a hoodie and a backpack. George Clooney famously loves the place, but he has a house there, so his opinion is compromised. Mine wasn't. I felt the stares. I was a single hiker-shaped smudge on everyone else's honeymoon postcard.

And then I did Santorini. Solo. Which is Lake Como times a thousand.

I'll quote myself, because I apparently saw the story coming years before I wrote it: Santorini, I once put in my old blog, has so many lovers staring into each other's eyes that "it makes a solo traveler consider leaping into a live volcano." That was a joke. Mostly. But it's also the exact emotional coordinate of Jeff's entire trip, the man on the sunset terrace surrounded by couples, pricing out the caldera. When I gave Jeff that feeling, I wasn't imagining it. I was remembering it. One difference: I was staying in Fira, not Oia.

The Volcano You Joke About Leaping Into

The real highlight of my solo trip, and this is true, not a bit, was the volcano boat tour. Santorini is a volcano; the whole impossible crescent shape is the rim of a caldera that blew itself apart. You sail out across the water to the still-steaming center of it, and on the way the wind kicks up and the boat pitches and I, a person who was at the time literally in the U.S. Navy, came embarrassingly close to being seasick. We stopped at the little island of Therasia; the views back toward Oia were the best of the trip.

In the story, the volcano boat tour is where Jeff finally meets someone who gets it, a recently divorced mom on the ride back. That's not an accident. The volcano is the one place on Santorini that isn't romantic, which makes it the one place a lonely person can breathe. I put Jeff's only real human connection out there on the water, as far from the sunset terraces as the island will take you.

The Beaches That Beg for a Metaphor

Santorini's beaches come in colors, courtesy of the volcano: the Red Beach near the Akrotiri ruins, the black sand of Perissa and Kamari. As a kid I wanted to be Indiana Jones, so wandering the actual Bronze Age ruins at Akrotiri was its own small thrill. But it's the colors that did me in as a writer, a beach that is visibly, literally red or black is practically begging to be turned into a feeling.

So I let Jeff do it. He reads the black sand as the shock of the betrayal, and then stands on the Red Beach watching a honeymooning couple and wonders, bitterly, where the green beach is, the one for his jealousy. Those metaphors are a little unhinged, which is the point. But I'll admit the beaches handed them to me. I just stood there, years earlier, and felt the island inviting the comparison.

Oia at Sunset, or: the Loneliest Crowd on Earth

Everyone tells you to watch the sunset from Oia, and everyone is right, and nobody warns you what it's actually like: hundreds of couples packed onto the Byzantine castle ruins, each convinced they're having a private moment, competing politely for the same six feet of golden light. It is the single most beautiful place to feel alone that I have ever stood.

That's the scene the whole story is built to survive. Jeff sits in that crush while a woman on FaceTime angles her phone to avoid including him in the frame. I didn't make that up either. When you're the solo one at the Oia sunset, you become something people subtly compose out of their photos. You are a flaw in the postcard.

A Word About the Donkeys (and Hector)

In the story there's a donkey named Hector who hauls tourists up the stone steps from the old port to Fira, and whose handler, asked why the animal does it, shrugs: "What else would he do? This is his purpose." Hector is invented. The donkeys are not. They really do work those steps, and I'll be honest that watching how hard they're worked sat uneasily with me, the same discomfort that, in another life, once turned me vegetarian for five years. I gave Jeff a moment with Hector because the donkeys were the one thing on that glossy island that looked as tired as he felt.

The Confession I Owe the Island

Full disclosure, since this is the Notebook and not the brochure: three of the photos doing real work in the story were never shot on Santorini at all. They're from Naxos.

Here's the thing nobody tells you, all the Cyclades wear the same whitewashed, blue-domed uniform, so a picture from one island slips cleanly into a story about another. The smiling dumpster that finally cracks Jeff up near the end? Naxos. The hollowed-out cucumber he stares at as a metaphor for his emptied heart? Naxos. Even the Mother Teresa quote painted on a wall, the one that lands like a cosmic insult at exactly the wrong moment? Also Naxos. I spent time there too, in a white-marble mountain village called Apeiranthos that honestly felt more real than Santorini's Instagram crush, and those three odd little shots came home and quietly stood in for the famous island. Three of the story's beats are wearing a disguise. Now you know which. And here’s a small happy ending the story never gets to show: at a cooking class in a Naxos home, I watched that same hollowed-out cucumber, Jeff’s emptied heart, get stuffed full again, beef and vegetables and all. The emptied heart, refilled. Which, it turns out, is the end of my story too.

The Part Jeff Doesn't Get to Have

Here's how I know the island isn't cruel, only honest: I went back.

Years after the solo trip, after Lake Como, after the volcano math, after being composed out of a hundred strangers' sunsets, Santorini became part one of my honeymoon. I returned as exactly the kind of traveler I used to watch with such resentment: half of a couple, with a reason to be there, a person to hand the camera to. I have stood on that same Oia terrace from both sides of the glass.

Which is probably why Jeff's story doesn't end in romance. It ends with him realizing the island's magic isn't only for couples, that beauty and a bad joke and a stranger on a boat are available to anyone who shows up. I believe that, because I was the lonely one first. Jeff doesn't get the honeymoon. But he gets the thing I actually needed on my solo trip, which wasn't a partner. It was permission to be there anyway.

"Not the kind of love I expected," Jeff says at the end. "But maybe the kind I needed." I wrote that line on the far side of my own honeymoon, about the version of me who hadn't had it yet.