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(Photo: Pack Up + Go)

Would You Book a Trip Without Knowing the Destination? These Travelers Did.

Ever wonder what it would be like to embark on a journey someone else planned for you, down to the lodging and airfare? Or does that thought send your brain and your wallet into a worried tizzy?

The outcome of a long-awaited trip often depends on how prepared you are for it. But one new travel service is taking all the planning out of the vacation process by sending travelers to mystery destinations—and it’s got the formula down to a science.

Pack Up + Go has sent hundreds of people to surprise U.S. cities since it started in early 2016. Based on some simple quiz feedback, the service sends you on a three-day trip for $650 to $2000 via your chosen mode of transportation (a flight/train/bus option, or a road trip). The price tag includes transportation and lodging, as well as a curated a list of locally recommended activities based on your given preferences. You don’t find out where you’re headed until the day you leave.

The process packs an element of surprise as well as the advantage of having a local expert plan your trip for you. But who exactly is willing to put their money and vacation time in someone else’s hands? What if you’re not crazy about the destination, show up ill-prepared, or the lodging isn’t what you want?

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I talked to three Pack Up + Go users to find out. Here’s why they opted to hit a mystery destination without any hand in the plans, and how that process plays out:

Tricia Moye, a Washington, D.C.-based attorney, tried it out for the first time this month. John and Sharon Shingara, from York, Pennsylvania, also tried the service recently.

Editor’s Note: These responses have been edited for clarity.

What made you want to use the service?

TM: I was intrigued by the idea of going on a surprise trip—both for surprise’s sake and for the convenience and time-saving aspect of not having to decide on a place and plan all the details.

J&S: John heard about the service on a Catholic podcast about letting stuff up to God and going with the flow. One of the commentators mentioned the service. … It sounded intriguing so he went online and looked it up. He’s a planner by nature and plans all of our travel, but we decided to book a trip through Pack Up & Go for his birthday so he could relax for a change and not worry about the travel arrangements.

Are you a planner when it comes to travel, or would you rather go with the flow?

TM: I tend to be a bit of a planner, although I don’t plan every second of a trip. I usually book my flights and hotel well in advance and research things to do … but I tend to see how I feel when I get there before deciding what activities to do. My last “big” trip was a week in Iceland with friends last October. 

J&S: John is a planner. I (Sharon) like to go with the flow. I travel for work on occasion but mostly within Pennsylvania and the surrounding states.  John doesn’t travel much for work.  We travel for pleasure. Our last trip was a cruise to San Juan, St. Thomas, St. Marten and Haiti.

What’s it like to hand over money for a vacation that you know nothing about? Were you nervous?

TM: I wasn’t very nervous about the location itself—I’m of the mindset that there’s always something cool to discover, no matter where I end up.  The wild card for me was the lodging—the survey didn’t seem to have a lot of questions geared specifically towards that, so I had no idea what the standards would be. But, I was pleasantly surprised—I stayed in a great hotel.

J&S: We were a little nervous about paying for a trip that we couldn’t control, but that turned out to be part of the fun. John was worried that he wouldn’t like the destination and was concerned about staying in a bed and breakfast. We had never stayed in one and didn’t know what to expect, but we loved it and had a great time. Our hosts were really gracious. We took a look at the places other Pack Up and Go travelers had visited before (on the website) to get an idea of what we were in for. He was hoping we would go to Denver or Nashville. I really wanted to go somewhere down south.

What kind of questions did Pack Up + Go ask you to begin the booking process?

TM: The survey included a few open-ended questions so you could include any restrictions. You could list recent trips and upcoming trips … I had the opportunity to list any dietary restrictions, strong likes or dislikes, etc.

Then there were boxes to check off whether you prefer action, relaxation, or culture when you travel … you can check as many as you like. You can also select a variety of activities for their recommendations—hole-in-the-wall restaurants, cocktail bars, live music, flea markets, spas, family activities, and more. 

J&S: You take a survey and they ask personality questions. Like where you have traveled before, and your last trip.

How did you feel when the mystery destination was revealed?

TM: They sent an email about a week before the trip with the weather forecast for the mystery location, as well as a few suggested items to pack and the time I needed to be at the airport.

They also mailed an envelope to my house that contained the information about where I’d be going, my hotel, and all of the recommendations for restaurants and activities. I wasn’t supposed to open it until I arrived at the airport, and it was quite hard staring at that envelope all week! I finally discovered at the terminal that I was heading to Charleston, South Carolina. 

J&S: We received an email a week before the trip with the weather, our departure airport details, an arrival time, plus some hints about our destination. They told us the weather was in the nineties. We received a travel package four days before we left and didn’t open the destination envelope until we were at the airport.

I jumped around like a little kid when we found out we were going to New Orleans! I had always wanted to visit, but John hadn’t.  I felt a little guilty since it was his birthday weekend, but he ended up loving the food, music, and atmosphere. We are making plans to visit again for a week or so next year.  We would have never visited if it wasn’t for this mystery trip. What a great way to discover the city.

What was your favorite and least favorite part of the trip?

TM: My least favorite part of the trip was how hot it was. It was hard going to a walking city with such intense heat and humidity, but it was bearable.

There was so much great food—seafood, barbecue, Southern food. I had craft beer from local breweries and amazing handcrafted cocktails. A lot of the trendy restaurants required reservations ahead of time, which were not an option since I didn’t know where I was traveling.

But Pack Up + Go did a great job recommending restaurants with very high quality food and a fun atmosphere that you could walk into without a reservation. I wandered through some historic graveyards and did a walking ghost tour one evening, as recommended.

J&S: We loved the spontaneity of the whole experience. It was fun reading the information they included in the package about New Orleans on the plane, so we could plan out where we were going to visit during our weekend.

Our friends and family all had bets going on about where we were going to end up. Really smart on the marketing front because we told at least 50 people about our trip and posted about it on Facebook. Our least favorite part was we didn’t have enough time to see everything. A weekend was not long enough to enjoy New Orleans.  I hope Pack Up + Go adds longer trip offerings in the future.

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Associate Editor Shannon McMahon writes about all things travel. Follow her on Instagram and Twitter for more insight and adventures.

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