At Guess Where Trips, we specialize in one-day surprise road trips. Leave the stress of planning to us! We build each road trips around a general theme, so you might have an idea of what you’ll 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 small towns. 

The trips are intended to be surprises, but there are a few ways to get a better idea of where you'll be going:

Check our 'Trip Map: Our trip map allows you to see the general area of where each trip ends. 

FAQ: Each trip has its own set of frequently asked questions. Please read this section for a list of approximate round-trip driving distances from nearby cities. 

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. 

Your road trip includes a well-curated itinerary for the day with a focus on small businesses, cute shops, hidden gems, and unique locations.

Food, drinks, gas, and admission (if there is a fee!) are not included in the price of our trips.

If everyone is travelling together in the same car, you only need to purchase one trip. Otherwise, we recommend one trip per driver.

Our road trips are designed to be one day trips. Each trip takes roughly 6-8 hours to complete - this includes time spent at the recommendation and driving.

In the Before You Go booklet, we will tell you what time we recommend leaving for your road trip. Keep in mind that the later you leave, the less time you may have to spend at each stop.