100,000+ ROAD TRIPS SOLD
Guess Where Trips
Mystery, one-day, self-guided road trips.
Four surprise stops on every road trip.
Six road trips to choose from in the Chicago and Milwaukee area.
Handpicked and well-researched road trip stops.
Gift wrapping available to help elevate your gift.
The ultimate experience gift!
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Mystery Road Trips
Cozy Cafes
Start your day off with a tasty treat from a local cafe or market.
Historic Highlights
Detailed and interesting history on the sites you're visiting.
Picturesque Trails
Stretch your legs on an off-the-beaten-path trail.
Quirky Photo Opps
Fill your camera roll with unique sites and road side attractions.
My husband and I did this and put our phones down, no work talk, no kid talk. We went on a date just the two of us and took the time to get to know each other all over again while experiencing stops along the way that we would never have thought to go to.
Tracy
Verified Buyer
We had an amazing day. The trip was so well curated and we discovered so many places we never would have found on our own. Great mix of food, cute towns, and adventure! Highly recommend.
Amber H.
Verified Buyer
My daughter, her girlfriend and I did a girls day. We took this trip and had an incredible day! The locations where hidden gems we had never been to before - so many fantastic memories.
Carolynne M.
Verified Buyer
Frequently Asked Questions
What is Guess Where Trips?
At Guess Where Trips®, we specialize in self-guided one-day surprise road trips. Leave the stress of planning to us! We design each road trips around a general theme, so you will have an idea of what you might get up to during the day, but you won’t know where we’re sending you! We love finding new small businesses, hidden gems, cute cafes, and picturesque towns.
How do I know where I'm going?
Our road trips are intended to be surprises, but there are a few ways to get a better idea of where you'll be going:
1. Check out our Trip Map! This allows you to see the general area of where each trip ends.
2. Frequently Asked Questions: Each trip has its own set of frequently asked questions. These are located bottom of the specific trip page. Please read this section for a list of approximate round-trip driving distances from nearby cities.
3. Ask us! We're always here to help with any questions you might have. Start a chat with us or send us an email with your departure area and travel interests, and we'll send you our trip recommendations.
What is included in my package?
Your road trip includes a well-curated itinerary for the day with a focus on small businesses, cute shops, hidden gems, and unique locations.
What's not included: Food, drinks, gas, and admission (if there is a fee!) are not included in the price of our trips.
