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If you’re in a bit of a travel rut, a travel company called Pack Up + Go is here to change all that. Buzz60’s Josh King has more.
Buzz60

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 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.

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!

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.

Day 1

  • Accommodations: I arrived in New Orleans late morning and checked into the Ace Hotel New Orleans, a 15ish-minute walk to the famous French Quarter, just after noon. Jazz music permeated the room from a radio.
  • Food: Willa Jean near my hotel was on the recommendations list for brunch, so I stopped there for an avocado toast. I know, I know, not New Orleans food exactly, but I was thinking I was headed for a food tour later that day. The Southern hospitality was welcome: “You still doing OK, sugar?” one waitress asked me. I ate at Sylvain, an American restaurant in the French Quarter, for dinner. Pack Up + Go made a reservation for me though didn’t 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 beautiful reputation, from the Mississippi River outlook across the street to the stunning St. Louis Cathedral on the other side.
  • Nightlife: I couldn’t not go to the infamous Bourbon Street, where I witnessed expected no-open-container-law debauchery and enjoyed bartenders belting karaoke at gay bar Bourbon Pub & Parade. No LGBTQ locations were on my itinerary, which was a bummer. Rafson told me the LGBTQ box generally helps them determine what cities might be more accommodating for certain travelers. I also stopped by Cafe du Monde, where you apparently have to get beignets. It was worth it, despite the powdered sugar that engulfed my face.

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 strips of bacon and melt-in-your-mouth grits, this wasn’t the best meal to eat before my food tour.
  • Book stop: Beckham’s Bookshop was a secondhand bookstore that smelled of old books, aka the happiest kind of smell you can think of, so I was glad to see that as a recommendation from Pack Up + Go.
  • On my own: I stumbled upon the New Orleans Pharmacy Museum (not a Pack Up + Go recommendation) and discovered everything from ancient medicines to voodoo dolls. It was as creepy as it sounds.
  • Food Tour: Doctor Gumbo Tours introduced me to all kinds of New Orleans cuisine: fried pig skins, a crawfish-stuffed beignet, all kinds of hot sauces, gumbo, a po’boy, a muffuletta and more. The tour also focused on history, where we learned about who owned New Orleans (the French, then the Spanish, then back to the French and finally to the U.S.) among other interesting facts.
  • Ghost tour: After a quick dip in my hotel’s rooftop pool, I arrived at a vampire boutique (yes, really) for my Pack Up + Go prearranged ghost tour. No one else signed up, so the New Orleans Secrets tour was just my guide and me. She told me about everything from the villainous, murderous Madame LaLaurie to the convent that vampires were supposedly smuggled into with shutters boarding up the top floor. Yikes.
  • More nightlife and food: I somehow still felt OK walking by myself to Frenchmen Street, where I popped into a few places and heard some live music. I finished the night with a burger at friend- and Pack Up + Go-recommended Port of Call, perhaps one of the best burgers I’ve had in my life, no exaggeration. Meaty, cheesy and arrived within minutes: A+.

Day 3

  • Food: District was another Pack Up + Go-recommended location, and I ordered a cinnamon doughnut and egg-and-cheese biscuit.
  • Culture: I walked from the Central Business District to the Garden District after hearing from a friend about the beautiful architecture. Cemeteries in the city are built differently (i.e. graves above ground, because of the lower sea levels) and worth checking out.
  • Goodbye: Headed to the airport around 10:30 a.m., stuffed and wishing I could stay longer.

Who should go on a surprise trip? 

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

The next time I go to New Orleans, I’ll want to leave enough time for a swamp tour and steamboat trip down the Mississippi, not to mention a visit to the WWII Museum and a host of restaurants I didn’t get to try. With Pack Up + Go’s three-day itinerary, there was no way I was going to get to everything. 

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

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The mayor of New Orleans says the city is “beyond lucky” after tropical storm Barry failed to cause significant flooding or damage in the city over the weekend. (July 14)
AP, AP