Which Way? A Surprise Road Trip Card Game
Go on your own mini surprise trip with Which Way. Simply pick a card to reveal your next ...
YOUR NEXT ADVENTURE STARTS HERE
Explore Road Trips
A Better Way to Hit the Road
Some of the best places are the ones you never would have thought to visit. Guess Where Trips makes it easy to find them, with self-guided road trips packed with hidden gems, quirky roadside stops, and unexpected discoveries. We do the planning so you can spend less time figuring out where to go and more time out exploring.
There are two ways to hit the road with us. Our Classic Road Trips turn four stops into a full day of exploring, while our Road Trip Boxes give you 20 mini road trips to enjoy whenever you feel like getting out of town.
Whether you're planning a full day away or looking for a quick change of scenery, we'll help you find something worth the drive.
Choose one full-day surprise trip, or a box of 20 shorter trips near you. Every route is road-tested by our team.
Your destinations stay sealed until you’re ready for them. Open one stop at a time, or one trip at a time, and let the day unfold.
Hidden gems, local favorites, and stories you won't find on Google. That's what's waiting for you.
General FAQs
What is Guess Where Trips?
We design surprise road trips where the destination isn’t revealed until it’s time to hit the road. Choose a Classic Road Trip for one full day of surprises, or a Road Trip Box with 20 shorter trips to pick from based on the season, distance or your mood. Then follow your self-guided itinerary as the day unfolds.
Every trip is filled with hidden gems, roadside stops, local favourites and unique experiences you might never have discovered on your own. It’s a chance to explore somewhere new and make lasting memories, right in your own backyard.
What is the difference between a Road Trip Box and a Classic Road Trip?
A Classic Road Trip is one full-day surprise adventure, available by mail or digitally. You open 4 surprise stops one at a time, with booklets full of stories, tips and maps along the way. The day remains a surprise until you open your next stop.
A Road Trip Box holds 20 shorter trips in one box. Each trip has 3 stops and takes about 4 to 6 hours, so you can pick one based on the season, distance or your mood, then save the rest for later. Each envelope unlocks a detailed online itinerary with maps.
Want one big surprise day? Go Classic. Want lots of shorter adventures to choose from? Go with a Road Trip Box.
What is your return policy?
Buy with confidence! Return your product within 30 days.
Shipping: $8 flat rate, free on orders over $100.
Standard shipping takes 4–10 business days. Need it faster? Choose the fastest option at checkout for 2–4 business day delivery.
Exchanges: Want a different item instead? Email us at questions@guesswheretrips.com within 30 days of your order.
Classic Road Trip FAQs
Physical vs. digital, what's the difference?
Classic road trips have two options: the physical (mailed) version, or digital (emailed) version.
A physical trip comes in the mail as 5 sealed envelopes: a "Before You Go" guide, plus 4 surprise stops you open one at a time as your day unfolds. Since it ships, it takes a few days to arrive.
A digital trip has the same 5 sections, sent instantly to your inbox after checkout. Since it's all one document, just go section by section and try not to peek ahead.
How do I know where I'm going?
You won't know the exact destination ahead of time, but you'll have a good sense of the area:
How long does a trip take?
Plan for a full day of adventure! Most trips include4–6 hoursof exploring, plus the drive to and from your starting point. We recommend choosing a trip that's about2.5–3.5 hours round-trip from homefor the best experience.
Do I need to book anything?
No advance planning needed for your road trip itself - since it's self-guided, you can pick any date. We do recommend the best days of the week and seasons for each trip, so it's worth checking those before you go. Some stops recommend a reservation, and we'll flag those in your "Before You Go" guide so you know ahead of time.
Road Trip Box FAQs
What's in the box?
20 sealed envelopes, each with its own trip, plus a map showing the general area of all 20.
Which box should I choose?
Pick the box closest to home. Day Trip Boxes are named after the nearest major city, but the trips take you to towns and hidden gems outside of it. Getaway Boxes cover a whole province or state, so they’re best for longer adventures.
How long does a trip take?
Each trip in a Day Trip Box takes about 4 to 6 hours, so it fits easily into a Saturday afternoon, a day off or a spontaneous weekend plan. There’s plenty of time to linger at your favourite stops without feeling rushed.
Getaway Box trips are built around iconic spots across Ontario or New York, so how long they take depends on where you’re starting from. Some might be an easy day trip from home, while others make a perfect excuse for a weekend away. If you decide to stay the night, each trip includes suggestions for where to stay so you can plan at your own pace.
