Why You Should Take a Romantic Vacation With Yourself

How a spur-of-the-moment trip to Greece changed this writer's life.

Photo: Getty Images

It was a rare, rainy night in Los Angeles. Sitting in a friend's apartment, fresh off a new job offer at a bi-coastal publication, lit by the glow of a sputtering MacBook Pro, and surrounded by the warmth and comfort of fluffy blankets and a micro Jack Terrier, the weather felt like a sign. Up late, scheming and googling, a $650 round-trip ticket to Athens with a 16-hour layover in Moscow, suddenly didn't seem crazy.

With a week off in between jobs, it was the ideal time to take a cheap, last-minute flight somewhere. Anywhere. Far enough to feel like an adventure, but not so far that I couldn't get back for work Monday. Newly 30, this would be my first "adult" vacation—a solid week at budget hotels instead of friend's couches or crushed into a crowded hostel—and my longest time spent alone. There was the pull to go somewhere new, experience a foreign language, cross some threshold of maturity. I had always imagined a trip like this would be with a partner—a boyfriend, fiance, a best friend—but after seven years single, and no one willing to drop everything and take a last-minute trip to Athens, I had to seize the moment, suppress the voice that says, "What if you get lonely? Or something terrible happens? What if someone needs you for work/ life/ basic home repairs?" I clicked "buy" and started googling "Greece."

I knew precious little about Greece, and to be honest, it never ranked highly on my to-see list. It seemed like a place where rich people hung out on yachts, and impossibly thin and tanned couples strolled slowly on the beach, laughing into the Aegean winds. The rest of my knowledge came from high school history classes and the vivid, illustrated books I'd read as a kid filled with vengeful gods and seductive goddesses, animals that played the pan flute, and a bull-headed monster with a giant house. None of this seemed to mesh with a single woman of limited means, living with roommates, and the deep desire to not have to spend too much time with other tourists. But some light internet research showed that Athens was not only highly walkable, it had affordable accommodations, specially in the shoulder season, and offered endless day trip potential via a cheap ferry system.

In hindsight, my only regret (other than spending 16 hours in the Moscow airport) is not springing for a nicer hotel in Athens. The off season is a great time for rock-bottom prices, and I had limited myself to $25 a day, staying in a four-floor hotel in the black market calling card district. But what the hotel lacked in ambiance and amenities, my explorations throughout the city made up for.

Each morning I'd ask myself, "What kind of adventure do I want to have?" This was an unheard-of luxury, as regular life was filled with work, after-work plans, freelance side work, and the daily obligations of being a functioning member of society. But on vacation, I could shed some of that worry and obligation. I could walk the city from dawn until I collapsed, immobilized with exhaustion, stopping along the way into tiny side cafes, drinking coffee at the base of the Parthenon, disappearing into the frenetic rhythms of the morning fish market, or exploring the city's kaleidoscopic graffiti art scene. Since I was alone, people were friendlier, more helpful and outgoing—and I also became a friendlier version of myself, joining communal dinners and toasting with a shot of Ouzo. Curiosity heightened, it attracted experiences I wouldn't have had with a partner, like spending the morning with a group of women who had set up a makeshift village to protest the plight of domestic workers, their logo a clenched fist wrapped in a red rubber glove. They were single, married, widowed, empowered, vibrant, and alive. I still have the sign they gave me, framed, in my apartment.

"I am loving your Eat, Pray, Love photos," a friend replied to one of my Instagram pics. It hadn't occurred to me I was on a journey of ephemeral self-exploration, but I had certainly eaten my weight in spanakopita. Something had changed, moved forward. Sinking into the experience, time and space felt like an option. When had I gone to the Temple of Athena as the sky turned purple? Visited Delphi to see where the Oracles had predicted the future? (The guide told us many were actually young women experiencing the effects of a hallucinogenic gas leak, but that only heightened the experience.) One of my favorite days was spent wandering the hillside ports of Hydra, where Leonard Cohen lived and wrote some of his most contemplative songs. I imagined him overlooking the harbor, the freedom of the sea and salty air, and understood, perhaps for the first time, what travel is supposed to achieve: it's not about running away, but running towards yourself.

Traveling alone, as a woman, raised eyebrows. "Are you married?" "Why not?" "Why are you by yourself?" "Don't you feel unsafe?" "What's back home?" "Does journalism pay well?" I sensed with clarity that my mind's tape recorder had not necessarily been the sole product of anxiety, but also external forces—at wanting adventure but not achieving what those expected a woman of my age to have secured.

That final weekend, I took a passenger plane to the volcanic island of Santorini, widely known as one of the world's most romantic honeymoon destinations. Mid-January, it was blissfully empty, the tourist shops closed for the season. I was one of only four people on the rickety bus from Fira to the ancient city of Oia, traveling to see the legendary sunset of postcards and hashtags. Disembarking, I walked up the hill for a better view, the only sign of life was men putting a fresh coat of paint on the island's famous bleach-white domes. At sundown, I scaled a wall for a better view. Never great at rock climbing, or really any sport, I wasn't surprised when the concrete became too slippery. I lost my footing and snagged my wrist on a sharp rock, cutting it, banging up my knee. "This is exactly what my mother worries about," I thought, frustrated. The combination of both being hurt and viewing the sunset alone made me wish I had a partner, but the thought was fleeting. I got down and walked towards the bus stop.

Sitting on the wooden bench overlooking the steep hills, leaning over the blue caldera, a man—roughly my age—came out of a nearby cafe. Tan, with thick black hair and an impenetrable beard, handsome in a way I was unfamiliar with—like he could cut down a tree and build me a home with it—he ran the cafe and asked if I'd like to try his lamb burger in flawless English. He explained that he'd spent the last year traveling through the American South to learn how to create the perfect burger. That he loved America, but Santorini was his home. That he had left paradise to chase after this singular dream was so pure that if this were a Nancy Meyer movie, we would have gotten married and made burgers on that mountain top forever. But this wasn't a movie, and to be honest, this life refresh had given new purpose to my own dreams. Because this is what travel also does: it allows you to escape the ideas you have about yourself, the script you've learned, to try on other lives. I starting seeing "singledom" not as a burden but an opportunity. Even if I never found a partner, I could, financial conditions willing, always get on a plane. I would be fine.

When I got back, things felt different. I began going to events that normally would have intimidated, took on more ambitious projects. Ironically, a few weeks after returning, I went on a first date with my current fiance. A film editor, tall, with great hair and a passion for his work, in some ways he reminded me of Mike with his burger stand. I am loathe to say that traveling alone allowed me to "find love," but it certainly left me open to meeting different kinds of people, to put myself into uncomfortable situations, and push the limits of my own heart's desires. I know I'm not alone: women are traveling solo more than ever, and American women rank first in frequent solo travel. I hadn't thought of traveling alone as a "feminist act," or even a particularly popular thing to do, but it certainly seems to be catching. And with all its benefits, why wouldn't it? Travel has the power to make people more present, more ourselves. And if that isn't worth the price of a ticket, I don't know what is.

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