I came to the airport with a backpack, carry-on luggage, and no idea where the plane I was about to get on would land. In my hands I held a large white envelope that I was forbidden to open until I had arrived at the terminal. (Inside: Information about where I was actually…going.) The arrangement made me feel like a secret agent or a mafia assassin or James Bond. In fact, I was off on a weekend adventure somewhere in the United States.
I had been smarting from a recent breakup when I saw a post from Pack Up + Go on Twitter. The service bills itself as a “surprise travel agency,” and I clicked through, intrigued. Pack Up + Go promises to handle logistics and booking. The catch, as the company puts it, is that the destination is a surprise.
It was about to be Valentine’s Day, and a vacation seemed like the perfect distraction from a weekend that I would have otherwise spent scrolling through other people's romantic Instagram posts while bingeing on drugstore chocolate and Bon Appétit YouTube videos in bed. Instead, I resolved to become the kind of person who took impulsive vacations without panicking at all. This Dana was bronzed, with nice sunglasses. She could paddleboard with perfect form. She never overpacked.
I can be impulsive—I’ve gotten piercings on a whim, and I’ve traveled alone before—but I often find I like the idea of spontaneity more than I actually like the spontaneity itself. More than once I’ve RSVP’d to an offbeat event on the other side of town—trivia! a concert!—only to realize that I would much prefer cuddling with my cat in my own home than talking to strangers.
The benefits of the surprise trip, I figured, would be twofold: The weekend would keep me from thinking too much about my ex, and it would give me several chances to take cute photos that I could post on Instagram so he would know just how little I was thinking about him.
Since its founding in 2016, Pack Up + Go has planned more than 12,000 trips for more than 22,000 travelers. Each trip is customized down to the smallest detail. “We have a team of in-house travel planners that plan all of our getaways,” says Corinne Hogge, the company’s director of marketing. “As our team grows, we’re starting to incorporate more data, but our destination-selection process is still hands-on.”
Once the travel planner has a destination in mind, that person works out logistics—finding a flight or train ride from the traveler’s home base, booking a hotel, and making sure the trip comes in within budget. (On the website, users can select how much they’re willing to pay for a weekend. For a solo trip, the budget options range from $1,000 to $5,000.)
One week before the trip, I got an email laced with clues like it was the first act of an Agatha Christie novel: the time I needed to show up at the airport, a weather forecast for the weekend, suggestions for what to pack, and a few tantalizing hints. (I was quite pleased to see “This city has some seriously good food!” among them.) Around the same time, a white envelope arrived, and within it the details of where I was headed on vacation.
I had promised myself that I would follow the “Don’t open until you’re at the airport” instructions. But that didn’t stop me from holding the envelope up to the window, hoping I could read the destination through the paper. The Pack Up + Go people were cleverer than me: Spoilers were blocked with a piece of paper that said: “No peeking.” Stupid psychic geniuses.
A mere 24 hours before takeoff, another email arrived: an updated weather forecast, and the terminal I would be departing from. A travel planner checked me in for my flight, so there was nothing I needed to do except get a good night’s sleep and make sure I remembered to pack headphones and a phone charger.
I knew it wouldn’t be a place I had traveled to before, which knocked out Chicago (where I was from), Providence (where I went to school), and New York (where I had lived). Cross off other random cities I had traveled to in the United States—Boston, Seattle, Orlando—and that still left a vast swath of most of the United States. I had guesses, but I didn’t know for sure until I pulled into the drop-off zone of Terminal 2 at LAX and decided I had waited long enough. I was going to…Austin, Texas!
Perfect! People seemed to like Austin! Austin was chic! I wouldn’t have to deal with the humiliation of returning to work the next week and trying to hide the crack in my voice as I told coworkers all about my fantastic mystery vacation to…Milwaukee. (Sorry, Milwaukee, I’m sure you’re great.)
The envelope also contained a folder of cheerful and well-organized information, providing me not only with fun facts about Austin—did you know the Texas State Capitol building in Austin is the largest state capitol building in America?—but also suggested stores and restaurants to visit and intel on the activities the good people at Pack Up + Go had booked for me. (After booking your flight and hotel, Pack Up + Go will spend whatever cash is left in your budget on add-ons. In my case, I got an Uber credit to help me get around the city, a restaurant reservation and prepaid meal, a “brunch tour,” and a massage.)
Usually, when I plan a vacation for myself or with a partner, I spend weeks reading blog posts and Rick Steves books. I download maps on my phone and punch in every location so I’ll never be disoriented. I look up the hours of museums and restaurants I want to visit so I never have an “Aw, I guess they’re closed on Tuesdays!” mishap. Call it being controlling or being a Capricorn, loving research or loving order; I am not the type to ever take anyone’s word on anything. I like to know where all of the pieces are on the board at all time—what’s happening with my job, my cat, my family, my boyfriend. Except now he was my ex-boyfriend. And he could be off doing anything with anyone he wanted (oh God). And I was here, learning that sometimes other people could plan things and it could turn out okay.
The real test of traveling alone came the next morning, when the time for that “brunch tour” arrived. It meant piling onto a bus with strangers while drinking mimosas as we drove from hot Austin brunch spot to hot Austin brunch spot. I arrived at the designated meeting place about 10 minutes ahead of schedule, prepared to befriend the tour guide and be the one sitting in front of the bus with her like the kid next to the teacher on a field trip. But the guide wasn’t there: I was faced instead with large groups of established friends in casual circles.
I approached a large knot of people who looked to be about in their early thirties. “Hey, you guys here for the tour?” I chirped. They murmured their assent and went back to their phones. I would need to try harder. “I’m Dana. Where are you guys from?”
One by one, they introduced themselves (they were nurses from Nebraska; these were their boyfriends and husbands) with varying degrees of complete disinterest. I felt like a college freshman desperately trying to make friends at orientation week, playing the role of the guileless, perky co-ed and not realizing everyone is just rooming with a friend they already knew from back home.
When I could no longer feign interest in the Nebraska boyfriends (“Oh, so you work in IT? Fascinating! What’s that like? No, really! I’m fascinated!”), I looked for a new mob of people to glom onto. A tall boy was checking his phone by a garbage can, next to a woman I assumed was his grandmother. I was right. They were from Canada, and every year the boy and his grandma planned a trip somewhere around the world—Tokyo, Paris, New York, and now Austin. I didn’t have to pretend to care this time. They were warm and charming, instantly adopting me into their little circle, sharing their beers with me on the bus and indulging me when I sheepishly asked for a photo of myself for the ’gram.
But then, one stop into the tour, the bus came to a complete standstill. It was the morning of the Austin marathon, and I had noticed that the past 20 minutes of driving had taken us in a big, slow circle.
The tour was an hour behind schedule. (The bus had been late getting to us…because of marathon road closures.) We had been sitting in traffic so long that two of the nurses asked to be let out to find a bathroom.
I had before me a daunting to-do list of all the places I still wanted to check out in Austin and a choice. And so I leaned into the best part of traveling alone: doing exactly and only what you want to do. I got the hell out of there.
With the help of an electric scooter and feeling just a little Bond-like, I whizzed around Austin, finding the indie bookstore that everyone had been telling me about, eating a doughnut the size of my face, seeing the LBJ Presidential Library, and capping off the day with an amazing meal at the bar of a gourmet restaurant.
Yes, going on a literal surprise trip meant there were little inefficiencies and doubling back. The trip didn’t work like a Swiss watch, but it didn’t have to. With the big-picture stuff taken care of, I just got to enjoy myself and come back to Los Angeles totally ready to take myself on a solo date to find breakfast tacos that can compare with the ones I had in Austin.
The notion of “dating yourself” always sounds like such a dusty prospect, like something from Bridget Jones or a self-help book. But when you’re zipping through a brand-new city, being alone didn’t feel sad or cheesy. It feels like freedom.
Originally Appeared on Glamour