I hate traveling alone. So when my editor asked me if I wanted to go on a trip — by myself — and write about it, I shocked myself by saying “yes.”
Don’t get me wrong: Getting paid to go on vacation? No-brainer. But there was one big catch.
Pack Up + Go, a Pittsburgh-based travel agency, launched in January 2016 and has sent about 16,000 travelers on 8,000 trips to 90 destinations across the country.
The catch? The whole trip, from the destination to what to do there, is a surprise. Pack Up + Go functions like a regular travel agency — and is a fully accredited one, according to founder and CEO Lillian Rafson — it’s just that travelers have no idea where they are going until the day of departure. Now it was my turn to test it out.
Here’s what happened, from when I clicked “purchase” on my trip to when I landed in my surprise destination to what I did when I arrived.
How does it work?
The premise is simple: Visit Pack Up + Go’s website, click “go somewhere” and select what kind of trip you want to take. I went for a solo traveler trip, plane or train. Every option is a three-day getaway.
You select your budget (mine was $1,000), hit purchase and are directed to a form. You feed the company a host of information about yourself and your intended plans, including but not limited to:
- Departure date (they need at least four weeks to plan)
- Several of the last trips you took/are taking next
- What types of activities you like to do on vacation
- Dietary restrictions
- What type of accommodation you’d like
- Airports you can leave from
I noted interest in live music, cocktails, LGBTQ, parks/nature, book stores, spas, history and mentioned I had spent time in larger cities like New York and Los Angeles.
Pack Up + Go was sending me … where, exactly? (Photo: David Oliver)
Pack Up + Go then works like a matchmaking service to fit the traveler with a perfect destination, using in-house travel agents to plan the trips. It’s a “low-tech, hands-on process,” according to Rafson.
Then comes the logic puzzle for Pack Up + Go: Does the traveler’s personality match the city? Does the trip fit into the traveler’s budget? Are hotels available those dates, or is there a major convention in town? Are there specific time restrictions that would make the trip not feasible?
Once the company settles on a destination, they collect sample itineraries laden with recommendations and place them in a thick, white folder to be mailed to the traveler.
It’s clear it behooves the traveler to give as much information as possible. “We always try to include recommendations for every single box that’s checked off,” Rafson told me.
The anticipation and the big reveal
A week before the trip, Pack Up + Go gives travelers a weather forecast for the destination, plus a few not-so-subtle hints about the place. In my case: Thunderstorms.
First thought? Uh-oh.
Pack Up + Go sent me this forecast a week ahead of my surprise trip. (Photo: Pack Up + Go)
The company then told me what to pack (walking shoes, a big appetite, clothes for a night or two out); how to pack (allowed one personal item and a larger carry-on suitcase); and where to go and when (7 a.m. at Washington Dulles International Airport, two hours ahead of departure).
An envelope arrived several days later, which I was instructed not to open until the morning of departure. I could see a “no peeking” warning through the large white envelope.
Based on the above hints — as well as mentioning the city is known for “vibrant culture” and “colorful streets” — I wagered it was New Orleans or Miami.
At this point, a possible hurricane was threatening New Orleans and flooding had already occurred. I started panicking. I kept Googling New Orleans weather and was thrilled (for the city and selfishly, myself) when the storm seemed to have left the city unscathed. Keep in mind this may not have been my destination at all!
I decided to purchase TripAssure travel insurance recommended by Pack Up + Go though, which clocked in at just above $35.
Rafson told me that had there been a formal travel alert from the airline on my departure date, the company would have reached out about possibly rescheduling.
I packed the night before and left the thick, white envelope next to my backpack and suitcase. When my alarm clock went off early the next morning, the first thing I did was grab it and furiously rip it open, the anticipation reaching an anxiety-fueled breaking point.
It was New Orleans after all!
New Orleans it is! (Photo: David Oliver)
What was the trip actually like?
The trip itself was — overwhelming! I’m a person who will happily go along with what the majority of a group wants to do on a vacation. But by myself? I clung to the two tours the company set up for me to create a semblance of a schedule for myself. Tours were not guaranteed and depend on leftover funds, so I felt lucky to have these tours at all.
The first day I was set for a food tour from 4 to 7 p.m., though Pack Up + Go emailed me just after noon to tell me the tour had been canceled due to flooding at several locations. I’m glad I checked my email; otherwise, I would have shown up confused! Pack Up + Go ultimately rebooked me for a different tour the following day, ahead of a planned ghost tour starting at 7:30 p.m.
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