It was 5AM and still dark when the tall Brit whose name I’d forgotten told me to get on the back of an idling motorbike. “This is Wa-Wa,” he said, gesturing to the gangly teen at its helm. “Go with him.”
I was standing barefoot in a bikini on the side of a pitted road in the Philippines, surrounded by a handful of strangers, and clutching my water bottle like a teddybear. I took a deep breath, ditched the bottle and got on.
My new buddy Wa-Wa pointed at the two surfboards teetering off the side of the bike and told me to hold them. I stretched one arm around the boards, the other around him and I’d barely lifted my feet before we were off. Twenty minutes or maybe two hours later, the bike veered sharply to our left and went flying into the jungle. That’s what you get for getting on the back of a motorcycle with a 15-year-old, I thought to myself. Also: my mother is going to kill me.
Before I could catch my breath, I realized we hadn’t crashed and were instead on what I can now, thanks to the generosity of hindsight, call a trail. 15 more minutes of bumps and branches and the jungle spat us out onto a tiny, white sand beach with crystalline waves rolling 50 feet off shore and, I shit you not, a rainbow arched across the sky.
I never thought I’d be so happy to find myself alone and half naked with a strange and pubescent boy on an empty beach on an island 48 hours and four flights away from my apartment in New York City.
I took my first solo trip almost exactly one year ago, at the ripe age of 31. It was a whim, mostly. I was long overdue for a vacation and decided to plan a girls’ trip to Nicaragua to learn to surf. But something happened as I researched. The more I read, the more excited I became, and the more I realized this wasn’t a trip I wanted to share. My time was precious—it had been a while since I’d had any days off—as was my money. The thought of compromising on a hotel or giving up a potential stop was already making me resentful—and I hadn’t even booked anything yet. I emailed my friends and bailed. (Technically speaking, I uninvited them. Sorry, guys!) It was the best decision I’ve ever made. (Well, at least one of the five best decisions I’ve ever made.)
Traveling alone for the first time is terrifying, especially as a woman, and especially especially if you’re someone who errs towards the more practical and responsible side of the life-living spectrum. What if something happens to me? What if I get lost? What if I’m miserable and do all the wrong things and end up regretting the whole trip? These are all valid thoughts—and, actually, important ones to consider when making the decision to go it alone.
To ease my own mind for Nicaragua, I ended up following in the footsteps of friends and acquaintances who had been before, which made me feel like my decisions on where to stay and what to do had been vetted. I also opted to dedicate half my trip to a retreat-like setting, specifically Buena Vista Surf Club in Playa Maderas, which is a great way to take some of the guesswork out of solo travel. (So great, in fact, that just a few months later, I booked myself on a five-day boating adventure in Palawan. And I’ve currently got my eye on this surfing retreat in Sri Lanka.) Pick something you’re into — yoga, photography, sailing — and I can guarantee there’s a retreat for it. Less into activities? Instagram geniuses El Camino Travel organize delightfully curated and immersive group trips to places like Colombia, Trinidad and Tobago, and, yes, Nicaragua.
Traveling alone leaves you eminently more open to meeting people, which is one of the best ways to explore a foreign place and immerse yourself in an unfamiliar culture. And probably what you’ll notice most quickly when you’re flying solo is how many other people are also traveling alone. Before the Philippines, I don’t remember the last time I made a brand-spanking-new friend out of a stranger. But on that aforementioned boat trip, I ended up camping most nights with a fellow solo female traveler named Kate. We still talk almost weekly.
In some ways, safety is the easiest hurdle to jump. There are plenty of things you can (and should!) do to be safe. Put together a detailed itinerary (including flight info and hotel numbers) and share it with your family. Pack lightly. Leave your jewelry at home. Check in with your family by sending a quick email or text, if you can, whenever you get to a new location. Don’t accept mixed or unopened drinks from strangers. Be mindful of your surroundings. None of this is earth-shattering stuff; just plain old common sense.
But the best part of doing anything alone is, well, being with yourself. Some of my favorite memories from these trips exist only in my head. There was no one else there to see it. No one to take a photo of me experiencing it. And trying to recount those particular moments, those sunsets, that taxi driver who took me to his favorite roadside fruit stand, the silent boat ride at sunrise out to a hidden reef, or, say, an empty white beach on a tiny island in country far, far away, is the perfect kind of impossible.
Which brings me back to that beach in the Philippines. I’m going back in November. This time I’m bringing my friends with me — and I can’t wait for them to meet Wa-Wa.
Photographed by Krista Anna Lewis; Flatforms designed and created by L. Michelle Reneau. Check out her Instagram @flatforms; flatforms are wearing Prada with a Steamline luggage stowaway and Dries Van Noten with a Prada carry-on.