Surprise Trips Are More Popular Than Ever—Here’s What It’s Like When a Stranger Plans Your Vacation

One AFAR editor let the surprise travel agency Pack Up and Go plan a mystery road trip—one where she didn’t find out her destination until the moment she walked out the door.

Surprise Trips Are More Popular Than Ever—Here’s What It’s Like When a Stranger Plans Your Vacation

AFAR went on a surprise road trip to Newport and saw historical landmarks like The Breakers.

Photo by Lyndsey Matthews

After I zipped up my weekend bag and put my shoes on, I eagerly ripped open the envelope that read, “Warning: No Peeking Until the Day of Your Departure!” The envelope had arrived on Tuesday, but through sheer force of will, I had managed to keep its contents—the destination of a weekend getaway planned by Pack Up and Go, a surprise travel agency—a secret until the moment I was ready to depart on Saturday.

I pulled out a thick piece of card stock that read, “You’re going to Newport, Rhode Island!” in big teal letters. And with that, I added the envelope—which also contained a pre-planned itinerary—to my bag and headed off on a road trip to the coastal New England city.

At AFAR, we’ve been big fans of surprise trips for a long time. Ever since our first issue in fall 2009, we’ve been sending writers like Alton Brown and Charmaine Craig to destinations such as New Zealand and Lisbon with just 24 hours’ notice in our “Spin the Globe” feature. Surprise travel has become a full-blown trend in recent years as more companies start to offer these trip-planning services.

In fact, Pinterest discovered that searches for “Surprise Destination” increased 192 percent in the last six months of 2018, beating out other popular travel terms like “Hot Springs” and “Autumn Scenery.” The desire to be more spontaneous appears to be at the root of this trend. In their 2018 Travel Trends Report, Ford Motor Company found that 52 percent of U.S. travelers said they enjoy getting lost and spontaneously discovering hidden restaurants and shops to create unique memories when they travel.


Exploring Newport in a 2018 Ford Mustang

Photo by Lyndsey Matthews

I’m the kind of traveler who finds great joy in researching destinations and poring over guidebooks months in advance of my trips, but when Pack Up and Go and Ford offered to let me borrow a 2018 Ford Mustang for a three-day surprise road trip, I jumped at the opportunity. As a travel editor, whenever I take off with my friends or family, I tend to handle most of the reservations and research. But sometimes, it’s nice to let someone else do the planning. For group travel it can be hard to pick one destination that checks all the boxes for your group.

But that doesn’t mean Pack Up and Go picks a place at random and sends you there. When I booked the trip, I took a short survey that asked me about the last few places I had been and where I was planning to go next (to make sure they wouldn’t send me on a repeat trip), and details about the kind of traveler I was. Do I prefer museums to shopping? A quiet night in or one out on the town?

Other than that, all I knew before I left were a few vague details. The trip would be in a midsize city within a four-hour drive of my home in New York (Pack Up and Go also plans air and train trips within three to four hours of your home for people without access to cars). I also received a weather report a week before departing. While the details I was given eliminated larger cities farther away like Boston and Washington, D.C., my mind swirled with the possibilities.

Technically, there was nothing stopping me from ripping open that envelope the second it arrived, but the secret was half the fun. The week before I left, my friends all sent me their destination guesses. Some thought Philadelphia, others were convinced it was either Baltimore or Annapolis, while exactly one friend guessed Newport correctly.

Pack Up and Go had also printed out directions to and from Newport’s Mill Street Inn, where they had booked me for two nights. The Mustang I borrowed was kitted out with Wi-Fi and Apple CarPlay, which made it easy to listen to my own music and get directions at the same time—without burning through my entire data plan.


No trip to Newport is complete without sunset drinks at Castle Hill Inn.

Photo by Lyndsey Matthews

In addition to providing suggestions for things to do once I arrived in Newport, Pack Up and Go also gave me conveniently timed suggestions for places to stop for lunch along the way (I never would have happened upon the SoNo Baking Co. in South Norwalk, Connecticut, otherwise). It was also nice to get off the highway and into Narragansett—home to one of the best beaches in Rhode Island—for a quick detour. When I arrived in Newport, I found the Mill Street Inn to be a bit understated for my tastes. But after waking up the next morning, I realized it was in the most peacefully quiet location while also being within a short walk or drive of other recommendations like the White Horse Tavern, Cliff Walk, and Castle Hill Inn. I can deal with beige decor for an undisturbed night of sleep and convenience any day. While Pack Up and Go’s suggestions were spot-on, Instagram was another trove of information for the spontaneous trip. I got brunch recommendations from a friend’s wife who had gone to high school in Newport, and also found out that a past colleague’s brother ran the Midtown Oyster Bar on Thames Street. So while I was enjoying a glass of sancerre and a half-dozen local oysters, chef James Mitchell gave me tips for where to find affordable lobster rolls (Anthony’s Seafood, just a 10-minute drive away in Middletown) and the best place to drink a pint next to locals (Pour Judgement on Broadway).

How to plan your own surprise trip

Pack Up and Go offers two-night, three-day surprise trips starting at $400. But Magical Mystery Tours, Surprise Me Trips, and the Vacation Hunt also offer these kinds of trip-planning services. If you’re confident in your trip-planning skills, you can also surprise a family member, friend, or significant other with a trip (FYI, Valentine’s Day falls right before the long Presidents’ Day weekend this year).

You can take one of two approaches: To build anticipation—and give your travel partner a little bit of a warning—pick a weekend that you’re both free and drop hints in the weeks leading up to it with details about the weather and any special gear to pack. Then when you get to the airport or load up your car’s GPS, reveal the secret destination. If your travel partner really enjoys being spontaneous, you can also secretly clear his or her schedule ahead of time and pack their bag for an even bigger surprise the day you depart.

>> Next: The Best Weekend Getaways in the United States

Lyndsey Matthews is the senior commerce editor at AFAR who covers travel gear, packing advice, and points and loyalty.
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