Experience a Surprise Vacation to Savannah, Georgia

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 organizes a trip for you based on a survey you fill out weeks in advance. They send you a suggested and detailed itinerary that you’re supposed to open when you’re about to leave. 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 iBestTravel. “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 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 reduce 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.”

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. However, trying to cram all of that into a few minutes at the airport wasn’t feasible. Consequently, I decided to give 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 oak trees and Spanish moss. The latter hung over the city’s cobblestone streets, creating a swaying canopy that resembled ghosts whispering to each other. That’s the thing about Savannah; ghost stories remain a popular pastime, with tales circulating about the city’s past on a nightly basis.

Exploring Savannah’s Unique Attractions

Learning about this undead history was one of Pack Up + Go’s recommendations, which I embraced by choosing a lightly comedic version of a historical tour as I roamed through the city at night. Old Savannah Tours, which also operates hop-on-hop-off trolley tours, began offering the “BOO Y’ALL” comedy tour in March. It made for a hilariously ghoulish few hours.

While stopped at a playground ironically 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.”

From a culinary perspective, Savannah’s food scene was delightful. Instead of researching countless restaurant recommendations and feeling overwhelmed, I opted for Pack Up + Go’s list of eateries, starting with a.Lure, where they secured a reservation for my first night. After enjoying deviled eggs and a creamy dijon pasta, I leisurely walked back to my hotel, the walkable Kimpton Brice Hotel, with a plastic cup of prosecco in hand, relishing the historic district’s open-container policy.

The next night, I indulged in gazpacho with a pimento cheese garnish and sweet potato ravioli with pecan cream sauce at The Olde Pink House. This 1771 Georgian mansion turned restaurant features a collection of small rooms, each with unique attributes—such as sloped ceilings and stately fireplaces.

From the lush squares to the sandy shores of nearby Tybee Island (another recommended spot on the itinerary), I explored Savannah with insights that would typically take weeks of research to acquire. It was a delightful fusion of spontaneity and rapid planning, as I absorbed the wealth of recommendations in just a few hours.

I realized that when I plan everything in advance, the day’s schedule occupies my mind, leaving me anxious about the next item on the list. This time, however, I played by the rules and only discovered my destination at the last minute. Consequently, I enjoyed the moment much more.

As I boarded the plane home three days later, I vowed to embrace a more relaxed approach to planning in the future.

Then, I discovered that my next surprise destination would be London, prompting me to make a list. Like Savannah’s ghosts, I guess bad habits die hard.