200,000+ road trips soldSurprise Trips, Planned for You.
Discover a new way to explore with self-guided surprise road trips. We plan the stops, find the hidden gems, and keep the destinations a surprise until you hit the road.
Surprise road trips
Self-guided & fully flexible
Hidden gems & Local stops
Road-tested by real people
Three Ways to Explore
One surprise trip, one perfect day. Pick a location and get a full day of stops, already planned and road-tested by our team.
20 surprise road trips in one box. Explore a new area whenever the mood strikes, one sealed envelope at a time.
Card games and guides for road trips you plan yourself. Hidden gems, local favourites and fun for the whole drive.
What's Inside Your Surprise Packages
Classic Road Trips
Best for: Planning a special day out, with surprises unfolding at every stop along the way.
- An 8–10 hour, fully planned road trip
- Four sealed stops you open as you go
- Packed with local stories and insider tips included in each booklet
- Available mailed or as a digital download
- Please note: Food, drinks, gas and accommodations are extra, but many activities are free or low-cost.
Road Trip Boxes
Best for: Having a variety of adventures ready whenever you're in the mood to explore.
- Twenty 4–6 hour adventures
- 3 curated stops on every itinerary
- Use the map and envelope clues to choose your adventure
- Each trip includes a detailed digital itinerary
- Please note: Food, drinks, gas and accommodations are extra, but many activities are free or low-cost.
Free shipping over $100
Covers your whole group
No booking required
2,328 verified reviews
See Where Our Road Trips Took Them
"I love that I can just grab an envelope and we have the entire day planned.”
“It's such a fun way to explore!”
@emilywhoexplores
“Would you try a surprise day trip?”
@morgan.exploring
"Every stop felt like a hidden gem"
@lexy_explores
“Perfect for a weekend adventure”
@paubarragann
"Skip the planning and just GO!"
@thewatsonpost
2,328 verified reviews
Thousands of Five-Star Reviews
Perfect birthday gift!
“I bought this for my husbands birthday. From the coffee shop, to the towns locals giving us some fun history ...it was amazing!”
Such a nice surprise!
We did the hops, hikes and history tour and it was so much fun! My husband begrudgingly came along for something I wanted to do, but he thoroughly enjoyed himself, as did our dog!?
What an incredible experience!
Yesterday, we completed the Hidden Hideaways trip, and it exceeded every expectation. It was one of the most enjoyable day trips we’ve ever taken!
Fun date day without having to plan!
Fun date day without having to plan! Took all the suggestions and made the most of our day. Didn't get to our final stop because we took so long enjoying the first three. Can't wait to do another one.
our story
Meet the Team
It started with a woman who wanted better weekends
Guess Where Trips started in January 2020, when founder Jessica Off created a scavenger-style surprise road trip as a gift for her parents. Six years later, we're a small Canadian team that has spent over 4,800 hours on the road so you don't have to figure it out yourself.
Woman-Founded
Small Canadian Team
Independently Owned
Every Stop Supports Local
Every business on our routes is local and independent. We've seen what showing up means. When you go, you're giving a small business a really good day too.
Local breweries
Charming small towns
Cozy cafés
Scenic lookouts
Farmers markets
Quirky photo ops
Roadside oddities
Hidden beaches
Independent bookshops
Heritage trails
