Guess Where Trips is a Canadian-based travel company that creates themed surprise day trip itineraries. You pick a theme online, they mail you a package with four sealed envelopes, and each one reveals your next destination.
Then you start with a recommended departure time, open the first envelope, and follow the directions. You don’t know the whole route until the day unfolds, which makes it feel like an adventure someone planned just for you, and it’s super affordable!
I started from Maryland, drove into Delaware, and ended the day in Pennsylvania.
How It Started & How It Went
When I booked the Whimsical Wonders experience with Guess Where Trips, I knew I wanted a day that felt fun and low-effort but still gave me new places to explore, and they did not disappoint.
I, on the other hand, disappointed myself when we parked at the first stop and I forgot my keys in the trunk because I was so excited to start the day. Luckily for us, Geico showed up quickly and unlocked my car while we still got to enjoy the adventure without a hitch in the schedule.
Stop 1: Marian Coffin Gardens, Wilmington, DE
The first envelope led me to Marian Coffin Gardens, a hidden gem on the grounds of the Gibraltar Estate. The gardens are beautifully maintained with stone paths, archways, and a variety of flowers and greenery.
I walked under shady trees and paused near the pond, taking in the calm atmosphere. It was easy to imagine this space in its prime, with grand gatherings and elegant, fancy outdoor parties.
The sculptures placed throughout the gardens made it even more picturesque. I took so many photos here and spent at least an hour, plus the wait for Geico.
Stop 2: Rockford Tower, Wilmington, DE
The second stop was Rockford Tower, a large and tall stone structure in Rockford Park. Built in the early 1900s, it was once both a water tower and an observation deck.
Although you can’t really go inside anymore, it’s still a striking landmark and a great spot for photos. The surrounding park had plenty of open space and trails, and I took a short walk before heading to the next stop.
Stop 3: Kennett Square Creamery, Kennett Square, PA
By midday, I was ready for something to eat, and the next envelope directed me to Kennett Square Creamery.
This spot is part beer garden, part community hangout, and serves everything from burgers to ice cream. I grabbed a late lunch and sat outside on the patio. The atmosphere was relaxed, and it was easy to see why this would be a favorite weekend stop for locals.
Stop 4: Chaddsford Winery, Chadds Ford, PA
The final envelope gave me options, but I went with the winery. Chaddsford Winery is known for its mix of red, white, and sparkling wines made from Pennsylvania and New York grapes. I enjoyed a glass on the outdoor patio while looking out at the lawn.
The winery sells cheeses and small bites, but I was more focused on the taco truck nearby, so I put together a light snack to go with my drink.
It was the perfect way to wrap up the day before heading back to Maryland.
My Honest Review
The Whimsical Wonders itinerary was exactly what I needed: a mix of scenery, history, food, and a little indulgence. Each stop felt different from the last, but together they created a smooth and memorable route.
The drive was easy, the packing list from Guess Where Trips was spot-on, and I appreciated not having to do any of the planning myself.
I’d recommend this trip for couples, friends, or even a solo day out if you’re looking to explore parts of your city or nearby areas that you might otherwise overlook.
Travel Resources
Resources to Use While You Plan
These are core guides and tools you can use for almost any trip, from picking a destination to mapping your route and making more time to travel.
All Itineraries & Trips
A central hub of long-weekend guides, Detty December routes, solo trips, and country itineraries you can copy and tweak.
Open itineraries hub →Solo Travel Starter Guide
A full solo travel hub with safety tips, destination ideas, and resources if you’re planning to travel on your own.
Open solo travel guide →Group Travel & Hosted Trips
Explore hosted group trips and trusted partner trips if you’d rather join a group instead of planning alone.
See travel options →COI Travel Network
A central page for solo, group, agency, and travel update links, so you can plug into my wider travel ecosystem.
Explore the network →How to Take More Time Off
A practical guide on stacking weekends, holidays, and smart PTO so you can travel more without quitting your job.
Read time-off tips →Trip Consultation Call
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