When it comes to travel, I have a Type A personality. I want to know where we’re going, what we’re doing and what the menus look like. Ideally, I’m the one making the plans.
A mystery trip curated by someone else does not sound like my ideal vacation. But despite my careful orchestrations, I still love to leave a little space to wander and discover new things. So when I got an email from a Canada-based company, Guess Where Trips, announcing that they were adding a series of journeys from D.C., the idea seemed palatable: They plan day-long road trips that are easy to reach from home, with several stops and multiple options on each leg.
The cost for a curated itinerary is $65, which doesn’t include gas, food or admission to any attractions. But with many options free, travelers can choose to spend as much or as little along the way as they want. Gift wrapping with a tote bag is an extra $10.
Mystery trip companies have been around for years, with many organizing days-long getaways that involve flights and hotels — and a considerably higher budget. Guess Where Trips tried organizing overnight stays early on, but found its niche with lower-priced staycation options.
Founder Jessica Off said more than 100,000 people have taken trips with the company’s suggestions since they launched in the summer of 2020 — a prime time for road trips. Staffers spend weeks researching, plotting stops on a map, reading forums and blogs and visiting destinations to figure out the best itineraries.
“For a lot of people, that’s the joy of traveling — planning things out,” Off said. But others “hate doing this and they just want something they can literally just buy. It will take them to new and exciting destinations, most of the stops are free, it comes in a pretty package.”
This planning fan decided to see how the other type of travelers live — and ordered the pretty package.
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The company — which offers trips in several Canadian provinces and a handful of U.S. states, including Florida, Georgia and North Carolina — added D.C.-area jaunts in June. (New York and New Jersey are coming soon.)
Customers can choose to have the information delivered in a PDF via email or by mail (delivery is free), with individually wrapped envelopes to keep each stop a surprise. I opted for snail mail, and the package arrived four days later. If I’d wanted to turn the day trip into an overnight, the confirmation email included links to hotel options — though clicking those would have revealed the destination.
There are five Guess Where trips from the area, most of them dangling hints about the itinerary but not spelling out a specific destination. One exception: a “Secrets of Gettysburg” itinerary that promised hidden gems and surprising stops.
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Other options included titles like “Tiny Town Tour,” “Haunts, Hikes & History” and “Winding Roads & Historic Gems.” General highlights and logistical information were available for each, along with information on potential stops that didn’t spoil the location and tips on dog- or kid-friendliness. A map shows the region of the destination without pinpointing a city.
My family has visited Shenandoah National Park and Harpers Ferry in the last couple of years and didn’t want to replicate those trips this time around; I’ve also been eager to explore more waterfront cities since moving to D.C. So we opted for the trip called “Waterside Bliss,” which mentions boardwalks, beaches and bites.
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A “Before You Go” envelope includes a recommended time to leave and general information about all four spots, including driving time from one stop to the next. Information about closures on certain days and a list of what to pack were important for planning purposes.
Our packet reminded us to bring walking shoes, bug repellent and coins for possible metered parking. A playlist is also recommended, but our 3-year-old would dictate ours (largely songs from Frozen films).
There were no clues that helped me with my typical road trip considerations: Where is the nearest playground? Can I get a good iced chai latte along the way? Will there be drugstores nearby? I took a cue from our playlist and decided to “Let It Go.”
Because my life is chaos, I didn’t open this pre-trip envelope until the day before our departure, only to discover an option on one of the stops would be closed the next day. For future trips, I would read this information as soon as the package arrived, in case I wanted to adjust the timing.
After double-checking the packing list — and adding the bug repellent and sneakers I’d forgotten — my husband, daughter and I piled into the car on a recent Sunday morning, departing about 15 minutes after the recommended latest time of 10 a.m. “Where we driving?” the 3-year-old asked. The question of the day!
The answer in the envelope? Annapolis, about an hour away.
On repeat, the playlist blasted an appropriate tune: “Into the Unknown.”
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Step one was “Waterfront Bites,” including a featured stop for a sit-down breakfast or two other options for a quicker meal. A tip noted we could get the food to go and eat on a tiny nearby beach, but I wasn’t keen to introduce sand and sun at the beginning of a full-day trip.
A list of fast facts about the destination mentioned architecture, historical facts, famous foods such as crab cakes and films and TV shows that were shot there, including “Patriot Games” and “House of Cards” — a fun way to set our expectations. We headed to the recommended restaurant, the bustling Bread and Butter Kitchen, waited for seats at the high-top counter overlooking a harbor and ordered the recommended dishes (hippy hash skillet and southern chicken biscuit, delicious).
The recommended time limit for the first stop was 45 to 60 minutes, but we blew past it; the restaurant was packed and it took longer for all of the food to arrive.
After a satisfying meal, it was time for the second envelope, which revealed our next move was a self-guided driving or walking tour featuring “historic hot spots.” It started just a few minutes’ drive away.
We found street parking, so we decided to walk to a few sites before finishing the tour in the car. We were still running behind schedule — on our way to the second historic hot spot, I realized it was after 2 p.m. — and the walk was warm, but it did lead us to a charming bookstore and coffee shop that wasn’t on the itinerary.
For me, that discovery was a huge bonus that let me engage in one of my favorite vacation activities (checking out a local bookstore) and delivered the iced chai I’d been craving.
For the third stop — “Boardwalk or History?” — we were immediately enthusiastic about the boardwalk. But then we realized that was closed on Sundays, and more of a nature trail stroll than the kind of fries-and-saltwater-taffy boardwalk we hoped for anyway.
We chose the open historic option in Edgewater, Md., which was 30 minutes from closing time when we arrived. Instead of spending $11 for admission, we sat in the shade of a historic home for a breather and gazed at the South River while our daughter rearranged rocks.
Our fourth stop promised to let us choose or own adventure with a series of appealing choices, including a kid-friendly park with great views of the Chesapeake Bay or a beach with nature trails. But by this time, we were too tired and sun-baked to try any of them. A winery also looked fun, but not with one member of the party pregnant and another many years away from legal drinking age.
So we chose the path of least adventure and headed to a nearby German restaurant for an early dinner — where the recommended Bavarian bauernwurst and apple strudel were winners.
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We finished the day wishing we’d spent a little more time near the water — but fully acknowledged that we chose the options that didn’t make that happen. In retrospect, it might have been too ambitious to expect to spend a full midsummer day outdoors while 8 months pregnant and accompanied by a small child.
While many trips are designated as kid-friendly, Off said that doesn’t always mean they will be best for toddlers. “Honestly,” Off says, that’s “the closest trip to home.”
One element of the trip stood out to us for delivering information that we might not have discovered on our own. The “Before You Go” document includes an acknowledgment that the history of some stops will be heavy, noting the “profound inequalities and systemic racism” that still result from slavery. We encountered that history at some of the places we visited, including one historic home that played a video describing its past with enslaved people and another location that is a “Site of Memory” affiliated with the UNESCO Slave Route Project.
Off said the company doesn’t want to skip over sites with such a troubled past, but does want to make sure attractions acknowledge their history. She said researchers also work to ensure recommended businesses are inclusive and safe for travelers of diverse backgrounds. The staff pores over reviews and social media accounts, talking to owners and visiting in person.
Would I take another mystery trip? Absolutely, and I would even do a second trip to Annapolis opting for some of the places we skipped the first time. Although the trips are designed to let people explore close to home, I would also consider them during a vacation or as gift for loved ones in other cities where they’re available. The excitement of an adventure (and wide variety of recommendations) made the $65 feel worthwhile.
I would do some things differently, like reading the pre-trip information further in advance, saving energy for later stops and maybe adjusting my timing for ideal weather. Because there are no reservations or tickets included in the purchase, it’s easy to be flexible about when to go. An updates section on the website shows information about closures or changes to schedules, still without spoiling the destination; the company recommends checking it before heading out, especially if much time has passed since the original purchase.
During the trip, I would also be more flexible. If a recommendation wasn’t right for my family’s needs, I would just skip it and move on to the next thing, or give myself a little time to amble around and discover something new. Even the most careful planners need to make space for serendipity.