10 tips for how to plan and execute your own big adventure.
“You’re so brave.” That’s what I hear a lot when I plan a solo trip. I don’t think of myself as a solo traveler — or brave — but somehow I’ve ended up recovering from Covid on a vineyard in Mendoza, kayaking Hawaii’s Napali Coast under a full moon, hiking the black sands of Dominica, and traveling to 19 destination weddings from Oregon to Oaxaca, mostly alone.
Safety aside (which is a legitimate concern, of course), why does traveling solo require bravery? Yes, the fear of the unknown can be intimidating, but most of the other big concerns are pretty easily dealt with. Afraid to be somewhere you don’t speak the language? There’s usually an English speaker somewhere nearby, and the Google Translate app is easy enough to navigate. Worry about figuring out the train schedules/routes? Your hotel or host can definitely help. Hate having dinner alone? I do that most nights anyway. And yes, it might seem better to share an experience with someone you love. But if that’s not in the cards right now, why miss out on the world?
People might see me as brave, but I think I’m just more willing to tackle the small obstacles that make travel challenging. And there are ways around all of them. Here’s how to embark on a solo journey of our “Lonely Planet” without feeling like you’re alone on the planet.
1.) Map Out Your Vision
Be methodical in creating your trip; build the foundation and framework ahead of time, so you don’t have to book travel while you’re traveling. Start with your ideal locations, then find places to stay, then figure out transportation between places A, B, C, and D. Restaurants can be booked in advance, but if you’re alone, it’s better to sidle up to the bar at a local enoteca than sit alone in a fancy restaurant. At least you know the bartender will talk to you (and feed you).
Once your reservations are set — at least for sleeping and transit — you can spend your time discovering hidden gems, ordering vino, and enjoying your gnocchi, not trying to connect with WiFi to reroute a flight. (Planning in advance goes for when you’re traveling with others, too; no one wants to chat about train schedules while they’re trying to enjoy the view.)
2.) Connect With People From Your Past, Present, and Future
Just because you’re going alone doesn’t mean you’ll be alone the whole time. Find people who live where you’re traveling: I DM’d my friend Elizabeth on Instagram even though we hadn’t spoken since the 1980s, saying, “Remember me?” She lives in Bologna and was so kind; she picked me up at my rental car drop-off, invited me to apertivo with her friends and dinner in her home, and told me where (and how) to go for coffee and catch the bus. People like to help you succeed on your adventure. Besides, you’ll meet more people when you’re alone instead of focused on a partner.
3.) Find a Group Activity
Group tours and classes, whether for a week or an afternoon, come pre-packaged with other travelers to talk with. My recent trip to Italy was planned around two major group activities: a wine-blending lesson in Montalcino and a healthy hiking adventure in the Apennine mountains. I met up with friends who’d just been at a painting school called PleinAirTuscany, where they created DIY masterpieces while staring out at the countryside.
Day-long activities are easy to book: In Bologna, I toured the food markets with Curious Appetite. The next day I met Maribel, a chef who teaches cooking classes in her home via Taste-of-Italy.com and serves her own Nocino, a liqueur she makes from green walnuts. I learned to make pici (hand-rolled pasta) in Montalcino with Magida from BrunelloCookingClass at Castello Tricerchi, a 13-th century castle and vineyard with a view. And Airbnb offers plenty of “Experiences” led by locals in virtually every well-touristed town across the globe.
4.) Pack Light, Physically and Mentally
Here’s what not to bring: a cowboy hat, your yoga mat, high heels, a bathrobe, or a hair dryer. These items are available pretty much wherever you go. (Other than the cowboy hat, but do you really need one?) Instead, bring one of each of these: a day dress, dinner dress, jeans, sneakers, sandals. Worst-case scenario, you can always find somewhere to do a quick load of laundry (or your hotel might do it for you). And think about multipurpose pieces: My Echo lightweight topper poncho served as an airplane blankie, day jacket, and evening wrap. Plus, half the fun of travel is finding gems wherever you are: I bought fluffy slippers on a side street in Siena for $16, enjoyed them all trip long, and then left them in my last hotel. Leave your “nice” jewelry at home — no one wants that kind of worry.
Psychologically, try to leave your baggage — and rigid planning habits — back home, too. Part of the joy of traveling solo is the freedom and ability to pivot and change plans at the last moment. Ideally, you want to be agile enough to say yes to a dinner invitation, beach party, or extended stay, should they pop up.
5.) Check Your Inbox and Make an Itinerary Before You Go
A lot of hotels and Airbnbs send confirmation emails and messages that require you to take action, like submit passport details or even a photo of you holding your passport. That’s much easier to do from the comfort of your own desk at home, so make sure to stay on top of deadlines before you go, with plenty of time to spare.
Once everything is booked, make one master document that has the addresses of everywhere you’re staying and all your important confirmation codes. Print that document and save a copy of it in your email and/or on your smartphone. A paper copy might feel old-school, but you’ll be grateful for it when you’re somewhere WiFi-less. In general, you’ll need to be organized, since there’s no one else to consult about the itinerary but you.
6.) Keep Up Your Health Routine
Don’t abandon your healthy habits just because you’re on vacation. Try to maintain the rituals that keep you grounded at home, because they’re even more important on the road. I travel with SEED probiotics and packets of AG1 powdered greens along with my drink shaker. So my morning routine on the road is the same as it is at home; taking care of my gut is especially important when traveling and eating all sorts of new things. While traveling, I do my Zoom yoga with Global Tribe Yoga whenever the timing works — if you meditate at home, meditate on the road.
7.) Bring a Book
When I traveled in Vietnam, I brought Stanley Karnow’s Vietnam so I could read about what I was seeing. My BFF Marcia DeSanctis is a travel writer, and her essays on journeying solo in A Hard Place to Leave are also inspiring. On my most recent trip, I read Pema Chödrön’s When Things Fall Apart, chock-a-block with life wisdom. A book keeps you company at dinner, in the hotel room, or on a train. And yes, you can download it to your Kindle if you’d like, so you don’t have to lug a hardcover everywhere.
8.) Make Google Maps Your Friend
Alone in Berlin, I chose a different museum or monument each morning, put it into Google Maps, and walked there. Google Maps works on GPS, not WiFi, so it functions whether or not you’re connected to a network. Just make sure your phone doesn’t accidentally slip into airplane mode, in which case Maps won’t work. Then you may end up wandering around aimlessly, as I did in Rome (which, to be fair, wasn’t the worst thing in the world).
9.) Stay in Touch With People Back Home
It’s OK to FaceTime your mother while you’re away. (The one time I didn’t leave an itinerary with anyone was when I traveled to Southeast Asia during what happened to be a tsunami in 2004; trust me, it’s better to stay in touch.) Assuming your phone plan functions overseas, FaceTime is completely free. When I had Covid in Argentina and was truly isolated because I had to be, I FaceTimed my friend Charlie every night, and we had a glass of wine together as if I were down the street. Though they may be many miles away, your friends and family are still there for you, even if you’re only connecting with them via Instagram. So you can view any loneliness you experience on the road as a truly temporary feeling.
10.) Remember That Leaving Is Harder than Arriving
You may get a little panicky when you’re departing alone for your big excursion — I did, on my recent trip (and took a Xanax). After all, you may be going far from loved ones, your pet, or your work. But leaving security behind is part of any journey, and you won’t think of them so much when you’re navigating daily life in a gorgeous foreign country (which that can be a very good thing). If you’re curious about a solo journey, I strongly encourage you to take a step into the unknown. As the saying goes, “Feel the fear but do it anyway.” That’s what traveling is all about.
Follow Martha on Instagram @marthamccully
