It’s sunset and I’m on a boat. “Fly Me to the Moon” is playing on some speakers. My hair is full of salt and sea air; in my hand is a glass of assyrtiko, Santorini’s traditional white wine. Do an online image search for “romance” and something like this will crop up. Except in the foreground there’ll be a couple. I’m here on my own.
When I told people I was going away alone, reactions were mixed. “That’s brave,” some said. “Good for you,” others condescended. Then I told them where I was going — and patronization turned to pity. Look, I get it. When you’ve never done it before, traveling solo to a honeymoon haven might seem a little masochistic. But for me that was part of the challenge.
I’ve long turned my nose up at the rising solo travel trend, particularly when it comes to women: what about safety? Aren’t they lonely? Don’t they get fed up with people looking at them as if they’re Bridget Jones?
Such concerns put me in the minority. Because research from British Airways found that more than 50 per cent of women have taken a holiday by themselves. Meanwhile, Google searches for “solo travel” almost tripled between 2015 and 2020, and there are currently more than 7.6 million #solotravel posts on Instagram.
Evidently going away solo is no longer unusual. Nonetheless it wasn’t until I’d gone through a break-up and realized that all my friends already had their annual leave all mapped out that I found myself contemplating taking the plunge. If I wanted to go on holiday, I had no choice but to go it alone. So I did.
I’ve always loved Greece: delicious food, kind people and the most beautiful beaches I’ve ever seen. With its dramatic landscape, unique architecture and famously spellbinding views, Santorini had been on my list for a while — and so, feeling resentful that its romantic reputation might put off single people, I decided to head there first. Then, for the sake of contrast, I’d visit Paros, a two-hour ferry ride away.
Obviously I was nervous. And in the run-up to the trip I had several visions of myself sobbing into a bowl of feta surrounded by couples snogging. Thankfully these feelings started to subside as my plans for the week came together.
In order to grasp the full experience of what it’s like to travel solo, I decided to split my time between rented accommodation and hotels. First up was a traditional cavelike villa tucked into the caldera in Firostefani, kitted out with an infinity pool and a view over Santorini’s famous volcano, both of which inevitably went down well with my Instagram followers.
Having arrived at sunset, I was thrown straight into the romance deep end. “You’re here alone?” my Australian neighbor asked, audibly shocked. “Yes,” I replied, proudly. “How’s that going?” he said, smiling and embracing his wife. “I’ll let you know,” I said before heading inside to get changed.
There are currently more than 7.6 million #solotravel posts on Instagram.
Dining alone was probably the thing I was most nervous about. This was remedied by going in armed with a fully charged phone and some books — I had a preview copy of Monica Heisey’s upcoming debut, Really Good, Actually, which provided plenty of laughs; Catherine Gray’s The Unexpected Joy of Being Single offered some much-needed enlightenment, even if it did feel a little too on the nose. It also helped that I limited my alcohol consumption, with most evenings involving two glasses of (dry white) wine and the occasional cocktail (always a negroni). Any more than that and I’d be drunk, which I thought was a state best avoided when traveling solo.
Food was one of the reasons I chose Greece, and even the simplest of meals didn’t disappoint — my lunchtime staple Greek salads, or the $3 street-food falafel I had for dinner one evening. Despite what I’d feared, restaurant staff never once looked surprised or confused when I said the words “table for one, please”. This was even the case at Lauda, a gourmet restaurant so romantic it has a special table with thronelike chairs that must surely be reserved for engagements.
Nongastronomic highlights of the trip came by way of Santorini’s famous hike from Fira to Oia — a difficult three-hour journey on which I fell over not once but three times because I was trying to take a selfie, ostensibly to show off the cliffs, but really to show off my new bikini; some people call this a “thirst trap”.
Then there was that boat trip: a five-hour tour to the island’s most scenic spots, including its red-sand and white-sand beaches. It was on this trip that I came to appreciate one of the most important parts of solo travel: meeting other people. With 16 on board, the boat’s cohort included Margot and Jack (a middle-aged couple from upstate New York), Dionne and Margaret (a professor and social worker from northern California) and their two teenage daughters, and Nico and Athena, a young couple visiting from Athens.
Within an hour all of us were huddled on the front deck, sharing stories about our lives. Heartbreak, divorce, existential crises — and Margot’s list of “hard nos” for Jack, which include letting him give directions (they’re always wrong) and driving (he once sat “in traffic” behind a parked car). Something about being a lone traveler made those conversations feel more intimate, the fleeting connections more meaningful. We all exchanged numbers.
I met others too. Like Maria, the Norwegian woman I shared a cigarette with on the ferry to Paros. And Josephine, the French octogenarian on the beach who asked where my lipstick was from.
There’s something about traveling alone that helps you to engage with everyone and everything around you on a deeper level (though I did love the quiet haven of my room at Andronis Concept, the hotel where I spent my final night on Santorini). Gone are the distractions of constant company and negotiations about which restaurant has a better Tripadvisor rating; it’s just you, so you notice more. Like the way that sand sticks to your stomach when you walk into the sea. The softness of cool bed sheets in an air-conditioned room. And the smell of sweat mixed with suncream that you wash off at the end of the day.
I had several visions of myself sobbing into a bowl of feta surrounded by couples snogging.
It was this mindset that took my trip to a higher plane even in the most seemingly isolating of circumstances. I’d go to a wine bar before dinner and be surrounded by couples — but instead of feeling lonely, I’d feel grateful. I’d look around and feel empowered by the fact that I’d chosen to come here on my own. That I could be perfectly content in my own company. That I was enough.
For whatever reason I felt this most viscerally in Paros, where my trip came to an end. The island was sleepier than Santorini, its towns less built up, its landscape more rugged. Even in the popular port town of Naoussa, where I spent my last night, there was an ease to the atmosphere. After failing to get into any of the restaurants that had been recommended by friends — being a solo diner does not give you an advantage here, sadly — I wound up in a cozy taverna called Yemeni, sitting at the bar, twirling pasta around my fork.
My phone stayed in my bag the entire evening as I sat there, recounting all of the highlights from the week in my head. When I returned to my hotel — a sustainable wellness retreat in the southwest of the island called Mythic Paros — I practically floated back to my room, a paragon of peace.
Whether you’re single or not, I couldn’t recommend a solo trip more highly. It has made me feel more liberated than ever, knowing that I don’t need a companion to travel with. Not having one was, in retrospect, the best thing I could have done for myself right now. Detractors might dismiss solo travel as Eat, Pray, Love fluff, but for me this trip really was a moment of self-development. I am proud of myself — and plans for my next solo trip are already in the works.
Olivia Petter is a freelance journalist who specializes in relationships, fashion, pop culture, and violence against women. She is the author of Millennial Love