I Went on a Surprise Vacation With Pack Up + Go — and It Changed the Way I Travel

Perched at a table at LaGuardia Airport in New York, I frantically thumbed through papers containing suggestions upon suggestions on what to do in Savannah, Georgia. I was minutes from boarding a flight to the southern city, yet I had absolutely no plans once I got there.

You can’t blame me of course, I only found out where I was going when I arrived at the airport.

I was headed on a surprise vacation with Pack Up + Go, a company that plans a trip for you based on a survey you fill out weeks in advance and mails you a suggested (and detailed) itinerary that you’re supposed to open when you’re about to leave. And for someone as Type A as I am, I knew it was going to be a challenge.

“These attractions and cities have the opportunity to surprise and delight you because you don't know what to expect in the first place,” Lillian Rafson, the company’s CEO and founder, told Travel + Leisure. “The idea is for you to experience a new place that you might not think to visit organically.”

Pack Up + Go has planned more than 10,000 trips since Rafson started the company in 2016. It was inspired by two women who were on a similar concept trip that Rafson met while backpacking up the Baltic coast. Pack Up + Go specializes in three-day weekend trips around the U.S., which she thinks helps with the unease of going on a trip you haven’t planned yourself.

“I think the fact that they are short trips really eases a lot of that stress and worry,” she said. “It's just a long weekend.”

So, after filling out the survey and noting that I was trying to be as spontaneous as possible — emphasis on trying — I was headed to Savannah (a city that, luckily, happened to be one of my top choices for the trip).

Normally I would spend weeks studying my destination, creating lists and itineraries — when I went on a road trip through Iceland, I had a minute-by-minute schedule — but trying to cram all of that into a few minutes at the airport wasn’t going to work. So instead, I gave up and gave in to the idea of not having a schedule and happily joined the throng waiting to board the plane.

Some of the first things that struck me about Savannah were the oaks trees and Spanish moss. The latter hung over the city’s cobblestone streets, creating a sort of swaying canopy that resembled ghosts whispering to each other. That’s the thing about Savannah, ghost stories remain a popular pastime, with hearsays circling and telling tales of the city’s dead on a nightly basis.

Learning about this undead history was one of Pack Up + Go’s recommendations, which I ran with, opting for a slightly different version that leaned heavily on stand-up comedy as I rode around the city in the dark. Old Savannah Tours, which also operates hop-on-hop-off trolley tours in a classic, black-and-white cab, started offering the “BOO Y’ALL” comedy tour in March. It made for a hilariously ghoulish few hours.

While stopped at a playground that, in an ironic twist of urban planning, was placed next to a former dueling ground, our comic tour guide joked that it was convenient “so the kids can watch if mommy or daddy won the argument.”

And diabetes is nothing to laugh at, he said, positing that “Thin mints have a higher body count than Jack the Ripper,” as we drove past the birthplace of Girl Scouts founder Juliette Gordon Low.

Thin mints aside, Savannah’s food scene was no joke. Rather than researching a million restaurant recommendations and feeling overwhelmed by the number of choices, I decided to go with Pack Up + Go’s list of eateries, starting with a.Lure, where they made me a reservation for my first night. After enjoying deviled eggs and a creamy dijon pasta, I strolled back to my hotel, the walkable Kimpton Brice Hotel, with a plastic cup of prosecco in hand — taking full advantage of the historic district’s open-container policy.

The next night I feasted on gazpacho with a pimento cheese garnish and sweet potato ravioli with pecan cream sauce at The Olde Pink House. The 1771 Georgian mansion turned restaurant includes a collection of small rooms that boast unique features — like sloped ceilings and stately fireplaces.

From the lush squares to the sandy shores of the nearby Tybee Island (another suggested spot on the itinerary), I ran around Savannah with the kind of insight I would have had if I spent weeks researching the trip. The trip was a combination of letting go and speed planning, trying to absorb the pages and pages of recommendations in only a matter of hours.

I realized that when I plan everything in advance, the day’s schedule is in my head and I’m always thinking about the next thing on the list. This time, I played by the rules (though admittedly, my mom tried to look up the flight schedule and guess ahead of time) and only found out where I was going at the absolute last minute. And I found myself enjoying the moment a little more because of it.

As I boarded the plane home three days later, I vowed to try to let go a bit more when it comes to planning.

Then, I found out I was heading to London and off I went to make a list. Like Savannah’s ghosts, I guess bad habits die hard.