Whether it’s fall, summer, spring or winter, Guess Where Trips has a fun day planned for you! Across Canada and the U.S.
We chose the “Picturesque Towns and Vibrant Vistas” as our planned trip in Southern CT!
It was Gilmore Girls inspired and brought so many good vibes our way. It was the perfect little getaway for my best friend and I.
The process of getting this trip was so easy, and it has super fast shipping. They tell you what you need to bring/wear and what time to go. They plan it all but it’s also all flexible, you can choose whether to do all the stops or just one. There’s no reservations needed for anything and most are free to enter. You get 4 stops included in the package with a ‘before you go’ envelope telling you all the details. The best thing about these trips is you can do them a million times over anytime!
I won’t spoil it too much but we had an amazing time. Our first stop included a cute cafe with some tasty flavors. They had coffees like toasted marshmallow, cookie dough and chocolate chip banana bread! So yummy. They had a sticky note guest window area where you could write a note for everyone to see. Included in this stop, we headed on a serene walk over a bridge in upper CT and then landed ourselves at our second stop.
Our second stop was awesome. We got to visit some of the cafes and historical marks that inspired Gilmore Girls but also had their own charms to them. We had an awesome lunch and enjoyed another coffee for good measure. This time we decided to skip the walk, only because it was a little chilly, and we decided it was the perfect time to open the third envelope.
The third envelope was our favorite. They gave us 3 options of breweries and vineyards to visit. We chose the oldest vineyard in the state to enjoy the rest of our day. They had a cute store in the bottom of the winery that had perfect holiday gifts for the family. On the second floor was the sitting and drinking room. We got a flight of different wines to try and we can confirm that they were all very good. They had a variety I had never tried before and it was fun to learn about them from the staff.
On our fourth stop, we only chose to go to the brewery and it was in the middle of Kent with nothing but trees surrounding it. It was nice weather at the time to just sit in the sun and sample the beer flight we had. They also had fun flavors like a zesty lime and a Kolsch!
We highly recommend Guess Where Trips for holiday gifts, birthday trips or just a day out of town! You can also book overnight stays in case you want the adventure to last all night.
See their different packages in states all over the U.S. and Canada! They have it in states on the Northeast coast and will take requests for trips elsewhere.
The ultimate gift for the road trip lover. Each box is beautifully wrapped (as shown in the photo) and includes:
- One gift card that can be applied to any trip with shipping & taxes included ($65 value)
- A Road Trip keychain ($8 value)
- Guess Where Trips Tote Bag ($12 value)
- Gift wrapping ($10 value)
“Hi there! I’m Jessica, the founder of Guess Where Trips. Thank you for stopping by and taking the time to learn more about us! Here are some fun facts about our team and the Guess Where Trips journey:
- The idea of Guess Where Trips originated from a Christmas gift I gave to my parents. I had planned an overnight surprise trip to Prince Edward County through a series of scavenger-style clues and envelopes. I enjoyed doing it so much, I started a business out of it!
- What started in my living room has blossomed into one of the most unique travel companies around, with trips in four Canadian provinces, and a growing list of US States.
- Our small, woman-run team consists of myself, a teacher, two history buffs and a social media wizard. Between us, we plan, create, design, print, package and ship all our trips from our office in London, Ontario. We all share a one major thing in common: a love for travel and adventure!
Our ultimate goal is to create an experience that will inspire you to step out of your comfort zone and explore your own backyard.
Guess where you’ll go next?”