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. 

Need us to take even more stress off of the planning and help you choose a trip? 

Fill out our quiz here to help you decide on a trip!

Our mailed road trips ($65) include a well-curated itinerary for the day with a focus on scenic routes, hidden gems, unique businesses, photo ops and a lot more. We pack the itineraries with travel tips, fun facts and stories about the places you’ll be visiting. Our trips come in five envelopes, which are tied with a bow and placed into a folder to keep everything neat and tidy. The digital version ($39) of the trip comes as a pdf.

Note: If you choose the PDF option, there are no surprise stop envelopes. All of the stops will be sent digitally to your email in one file, so scrolling through the entire document will reveal the surprise stops.

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

For orders over $50, we will ship your package for free.

Shipping within Canada

We use Canada Post for all shipping within Canada. Our (free) expedited option takes 5-7 business days.

If you need your order quicker, there is an Xpresspost option at checkout for $12.

Shipping to the USA

We use UPS for shipping to the United States. The free shipping option takes 4-8 business days, while the $15 paid option takes 1-3 business days.

Although we cannot book hotels on your behalf, we do recommend extending the adventure by turning your one day road day trip into an overnight getaway (especially if you choose one more than 4 hours round-trip from home!) Keep an eye out for your confirmation email! In it, we will send you a list of our favourite hotels in the end destination if you would like to extend your trip.

Each trip takes roughly 6-8 hours to complete - this includes time spent at the recommendation and driving. Under the FAQ section of each trip page, you will find more detailed information about the round-trip driving distance from nearby cities. This will give you a better idea of how much time you can expect to spend in the car, based on your departure location.

After choosing a trip, please enter your 16-character code on the checkout page in the field under ‘Have a Gift Card?.’ This will then take your order to a zero balance.

Kid-friendly: Yes! Almost all of our trips are kid-friendly. Click here for our kid-friendly trips. (This will show you all of our kid-friendly trips both in Canada and the US). We recommend choosing trips shorter in driving distance to ensure it’s a pleasant drive for everyone.

Dog-friendly: Many of our trips are dog-friendly or some what dog-friendly! Click here for our dog-friendly trips (This will show you all of our dog-friendly trips both in Canada and the US). The trip page itself will also let you know if it is okay to bring your pup or not. Note: most restaurants and stores do not allow dogs inside, so most of your day will be spent outdoors if you bring a furry friend along.

Yes! Many of our trips are wheelchair accessible and good for low mobility. On the trip page, we list if the trip is wheelchair accessible. Click here for a list of all our most wheelchair accessible trips. (This will show you all of our wheelchair accessible trips both in Canada and the US).

Most of the activities and attractions we recommend are free or have a minimal entrance cost (under $10/per person). We note the approximate costs per person in each trip package. If there is a higher entrance fee, we will recommend a free nearby alternative.