This travel agency is planning a surprise vacation

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 saying “yes”.

Don’t get me wrong: getting paid to go on vacation? No fuss. But there was a big catch.

Pack Up + Go, a Pittsburgh-based travel agency, launched in January 2016 and sent approximately 16,000 travelers on 8,000 trips to 90 destinations across the country.

The problem? The whole trip, from the destination to what to do there, is a surprise. Pack Up + Go operates like a regular travel agency — and is fully accredited, according to founder and CEO Lillian Rafson — travelers just have no idea where they’re going until the day of departure. Now it was my turn to test it.

Here’s what happened, from the moment I clicked “buy” on my trip to the moment I landed in my surprise destination to what I did when I arrived.

How it works?

The principle is simple: visit the Pack Up + Go website, click on “go somewhere” and select the type of trip you want to take. I left for a solo traveler trip, by plane or train. Each option is a three-day getaway.

You select your budget (mine was $1000), click buy, and are taken to a form. You provide the company with a wealth of information about yourself and your projects, including, but not limited to:

  • Departure date (they need at least four weeks to plan)
  • Several of the last trips you took/do next
  • What types of activities do you like to do on vacation?
  • Dietary restrictions
  • What type of accommodation do you want
  • Airports you can depart from

I noticed an interest in live music, cocktails, LGBTQ, parks/nature, bookstores, spas, history and mentioned that I’ve spent time in bigger cities like New York and Los Angeles.

Pack Up + Go then functions as a matchmaking service to provide the traveler with the perfect destination, using in-house travel agents to plan trips. It’s a “low-tech, hands-on process,” according to Rafson.

Next comes the logical puzzle of Pack Up + Go: does the personality of the traveler match the city? Is the trip within the traveller’s budget? Are hotels available on these dates or is there a big convention in town? Are there any specific time restrictions that would make travel impossible?

Once the company settles on a destination, it collects sample itineraries loaded with recommendations and places them in a thick white folder to send to the traveler.

It is clear that it is up to the traveler to provide as much information as possible. “We always try to include recommendations for every box checked,” 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, as well as some not-so-subtle clues about the location. In my case: Thunderstorms.

First thought? Oh oh.

Pack Up + Go sent me this forecast a week before my surprise trip.

The company then told me what to pack (walking shoes, big appetite, clothes for an evening or two); how to pack (allowed one personal item and one larger carry-on); and where to go and when (7 a.m. at Washington Dulles International Airport, two hours before departure).

An envelope arrived a few days later, which I was told not to open until the morning of departure. I could see a “no gaze” warning through the large white envelope.

Based on the clues above—along with mentioning that the city is known for its “vibrant culture” and “colorful streets”—I bet it was New Orleans or Miami.

At this point, a possible hurricane was threatening New Orleans and flooding had already occurred. I started to panic. I kept googling the 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 that this may not have been my destination at all!

I decided to purchase TripAssure travel insurance recommended by Pack Up + Go, which was just over $35.

Rafson told me that had if there had been an official travel alert from the airline on the day of my departure, the company would have contacted a possible postponement.

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 rip it furiously, anticipation reaching an anxiety-fueled breaking point.

It was New Orleans after all!

It's New Orleans!

How was the trip actually?

The trip itself was — overwhelming! I am a person who will be happy to accept what the majority of a group wants to do on vacation. But by myself? I clung to the two circuits organized by the company to create a semblance of a schedule. Tours were not guaranteed and depend on remaining funds so I felt lucky to have these tours at all.

On the first day I was scheduled for a food tour from 4-7pm, although Pack Up+Go emailed me just after noon to say the tour had been canceled due to flooding at several places. I’m glad I checked my email; otherwise I would have appeared confused! Pack Up + Go finally booked me in for another tour the next day, before a scheduled ghost tour starting at 7:30 p.m.

Day 1

  • Accommodation: I arrived in New Orleans late morning and checked into the Ace Hotel New Orleans, a 15 minute walk from the famous French Quarter, just after noon. Jazz music permeated the room from a radio.
  • Food:Willa Jean near my hotel was on the list of recommendations for brunch, so I stopped there for an avocado toast. I know, I know, not exactly New Orleans food, but I thought I was heading for a food tour later today. Southern hospitality was welcome: “Are you still well, darling?” asked a waitress. I ate at Sylvain, an American restaurant in the French Quarter, for dinner. Pack Up + Go made a reservation for me but did not pay for the meal.
  • Exploring: I walked through the arts district on my way to the recommended Ogden Museum of Southern Art. Next, I visited Jackson Square in the French Quarter, which lived up to its fine reputation, from the vistas of the Mississippi River across the street to the magnificent St. Louis Cathedral across the way.
  • Night life : I could not not go to the infamous Bourbon Street, where I witnessed lawless open container debauchery and enjoyed the bartenders doing karaoke at gay bar Bourbon Pub & Parade. No LGBTQ locations were on my itinerary which was a shame. Rafson told me that the LGBTQ box generally helps them figure out which cities might be more accommodating for certain travelers. I also stopped at Café du Monde, where you are apparently have to get donuts. It was worth it, despite the powdered sugar engulfing my face.
An overview of Jackson Square and St. Louis Cathedral in the French Quarter of New Orleans, from Washington Artillery Park.

Day 2

  • Breakfast:Luke in the Central Business District was on my Pack Up + Go list of places to go, and I enjoyed a hearty Southern breakfast. Between the bacon strips and the melt-in-your-mouth oatmeal, this wasn’t the best meal to eat before my food tour.
  • Book stop:Beckham’s Bookshop was a used bookstore that smelled of old books, which is the nicest kind of smell you can think of, so I was glad to see this as a Pack Up + Go recommendation .
  • On my own: I stumbled across the New Orleans Pharmacy Museum (not a Pack Up + Go recommendation) and discovered everything from ancient medicines to voodoo dolls. It was as scary as it sounds.
  • Gastronomic visit:Doctor Gumbo Tours introduced me to all kinds of New Orleans cuisine: fried pork skins, crawfish stuffed donut, all kinds of hot sauces, okra, po’boy, muffuletta and more. The tour also focused on history, where we learned who New Orleans belonged to (the French, then the Spanish, then back to the French and finally to the United States), among other interesting facts.
  • Ghost tour: After a quick dip in my hotel’s rooftop pool, I arrived at a vampire shop (yes, really) for my pre-arranged Pack Up + Go ghost tour. No one else signed up, so the New Orleans Secrets tour was just my guide and me. She told me everything from the wicked and murderous Madame LaLaurie to the convent the vampires were supposedly smuggled into with shutters on the top floor. Yeah.
  • More nightlife and food: I still felt good walking alone to Frenchmen Street, where I walked into a few places and heard live music. I ended the evening with a port d’ecall burger recommended by a friend and Pack Up + Go, possibly one of the best burgers I’ve had in my life, no exaggeration. Meaty, cheesy and arrived in minutes: A+.

Day 3

  • Food: District was another place recommended by Pack Up + Go, and I ordered a cinnamon donut and an egg and cheese cookie.
  • Culture: I walked from the Central Business District to the Garden District after hearing a friend talk about the beautiful architecture. The cemeteries in the city are constructed differently (i.e. graves above ground, due to lower sea levels) and are worth seeing.
  • Bye: Headed to the airport around 10:30, drunk and wishing we could stay longer.

Who should take a surprise trip?

I probably wouldn’t go on a surprise vacation again, at least not by myself. I would prefer this kind of adventure with at least one other person. But I learned that when traveling alone, I would prefer a more robust route than what Pack Up + Go offers.

Next time I’m in New Orleans, I’ll want to leave plenty of time for a swamp tour and a steamboat trip down the Mississippi, not to mention a visit to the WWII museum and… a host of restaurants that I couldn’t try. With Pack Up + Go’s three-day itinerary, there was no way to go to everything.

Still, this type of trip is for everyone, if only to expand comfort zones. After all: the best things in life often happen when ― and in ways ― you least expect them.

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