A Trust Fall Into Solo Travel: I Took a Mystery Vacation

Solo travel has always been on my radar, but taking the plunge and going on my first trip alone was daunting. Where should I go? What would I do when I get there? A million questions spun through my brain. Instead of picking a destination and planning a trip, I outsourced it to my siblings and decided to do a mystery vacation. 

They planned the entire thing and gave me an envelope the night before my flight with my mystery vacation revealed. It was a trust fall into solo travel that might not be for everyone, but it certainly was for me. 

What is a mystery vacation?

There are plenty of companies that specialize in planning a mystery vacation. You’ll give them a list of all the places you’ve traveled, your domestic/international travel preferences, your budget, etc., and they will plan the entire vacation for you. All you do is show up at the airport with an open mind.

They are also rather expensive. Brothers and sisters are free!

When I pitched the idea to them, they were immediately on board. Of course, I had to set the rules for this mystery vacation:

• 4-day trip, including travel days
• They cannot send me somewhere I’d already been (I gave them a list)
• Must stay within budget (spoiler: they did not)
• Must leave Louisiana (prankster family, this was an important rule)

I let them plan everything. It was equal parts refreshing and stressful. I was more stressed that they would break the rules and send me on some prank travel adventure where I’d be sent to Shreveport (no offense, Shreveport). 

Since I live in New Orleans, I also feared they would send me next door to Mississippi or along the Gulf Coast. I grew up on those beaches, so taking my first solo trip there was much less exciting than, say, anywhere else.

The day before the trip, my brother told me the weather predictions (so I could pack) and my flight time and gave me an envelope that would reveal my destination. I went home, packed, and the next morning, I headed off to the airport. 

Since I would only be gone for four days, I left my car at the airport. Once I parked, I opened the envelope to finally see where I would be spending the next four days. 

Charleston, South Carolina!

At first, I was slightly disappointed. I was sure they would send me to Chicago, Seattle, or Denver. Charleston completely blindsided me! I didn’t know anything about Charleston, and I only had a three-hour flight to figure it out.

Once I got on the plane, I went to work. I had no plans, so I had to figure out things to do in Charleston, where to eat, what to see… all the things! That part was sneakily stressful, and I didn’t account for the Supermarket Sweep-style planning I would have to do in such a short amount of time (and on the plane’s infamously bad WiFi).

My first hiccup was transportation. The envelope also revealed the Airbnb I would be staying at. My siblings didn’t choose an Airbnb in the most convenient location. I was neither downtown nor on the beach—just somewhere in the middle. It was a safe location, and the Airbnb was very nice—it just wasn’t close to anything. I had to rent a car at the airport, which was a surprise $300. A valuable lesson was learned on both sides of this mystery vacation. 

I spent the next two days wandering around downtown Charleston, visiting various beaches, shopping, and overall just enjoying my first solo travel adventure. I made sure to find a good spot for sunrises and sunsets. I was surprised at how many similarities there are between New Orleans and Charleston. It felt a bit like home!

I didn’t visit any museums, nor did I take any tours. I just merely existed in Charleston for four days by myself. And it was amazing. 

My goal wasn’t to go clubbing until the wee hours of the morning or have some profound moment of self-discovery. My goal was simply to take my first solo trip—mission accomplished. I’m sure most would find my itinerary rather disappointing. I didn’t visit any museums, nor did I take any tours. I just merely existed in Charleston for four days by myself. And it was amazing. 

I took this mystery vacation in 2018. Since then, I have traveled all over the world by myself, finding my soul in the Nordic countries underneath the Aurora Borealis. I fell in love with solo travel, and Charleston will forever hold a special place in my heart because of it.

I haven’t done another mystery vacation since Charleston, but I think it’s time. There’s something so freeing about relinquishing control and traveling just to travel. My sister is dying to have a second go at planning it, and maybe this is the year I’ll take her up on it.

I’d encourage everyone to do a similar travel trust fall and have a friend or family member plan a mystery vacation for you. It doesn’t need to be a grand, 10-day exotic adventure. It can be a long weekend like I did. You make the rules. 

Heck, e-mail me, and I’ll help you plan it.

Would you take a mystery vacation? Drop this article in the group chat and see who is willing to step outside of their travel comfort zone. If you need some travel inspiration, check out my picks for the best U.S. cities to travel solo.