Guess Where Trips

Guess Where Trips We're Guess Where Trips 👋🏻 and we plan one-day self-guided surprise road trips across Canada and the USA! 🇨🇦🇺🇸

No planning needed.
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Just open the envelopes, follow the stops, and enjoy the adventure. 🚗✨

Start here ➡️ https://guesswheretrips.com/

Ready for a road trip with a twist? 🚗At Guess Where Trips, we create one-day surprise road trips across Canada and the U...
06/17/2026

Ready for a road trip with a twist? 🚗

At Guess Where Trips, we create one-day surprise road trips across Canada and the USA, designed for curious explorers who love discovering new places. From scenic lookouts and charming small towns to outdoor adventures, local hidden gems, and unexpected attractions, every trip is packed with surprises.

How it works:
📍 Choose your trip theme and departure city on our website.
✉️ Receive your adventure, complete with four sealed surprise envelopes and a “Before You Go” guide.
🗺️ Hit the road and open each envelope as you go to reveal your next destination, along with directions, local insights, travel tips, fun facts, and exclusive offers.

Our trips are self-guided, flexible, and can be enjoyed whenever it works for you. Most stops are free or inexpensive to visit, making it an easy and affordable way to explore somewhere new.

Choose an instant digital download or have a beautifully packaged physical version shipped right to your door.

Travelling with friends or family? One itinerary is all you need for the group. If you’re heading out in multiple vehicles, we recommend one trip package per car.

🎁 Looking for a unique gift? Our surprise road trips are perfect for birthdays, anniversaries, weddings, holidays, or simply treating someone to a memorable day out.

Visit guesswheretrips.com or click the link in our bio to start planning your next adventure.

Proof that the coolest stories are hiding in places you’d never expect 📍 A famous movie location, a record-breaking land...
06/15/2026

Proof that the coolest stories are hiding in places you’d never expect 📍
 
A famous movie location, a record-breaking landmark, the prettiest little town in Canada, or a completely random fact you’ll be telling everyone for the rest of the week.
 
There’s always more than meets the eye. 🚗✨
 
Which one surprised you most?

🚨THEY’RE ALMOST GONE🚨Just a heads-up: we’re down to our last few copies, and the next restock won’t land until mid-Augus...
06/13/2026

🚨THEY’RE ALMOST GONE🚨

Just a heads-up: we’re down to our last few copies, and the next restock won’t land until mid-August.

So if you’ve got Ontario road trips and weekend getaways planned this summer… this is your sign to grab it now.

Packed with hidden gems, local favourites, and roadside stops worth pulling over for.

https://guesswheretrips.com/products/detour-diaries-ontario

06/12/2026

Red flags 🚩
Spending 3 hours trying to pick a road trip
 
Green flags ✅
Taking the Road Trip Quiz on our website and letting it choose for you
 
Comment “QUIZ” to find your perfect match 💘🚗

Sometimes the best Father’s Day gift isn’t a thing. It’s a day spent together!From scenic stops and local breweries to i...
06/09/2026

Sometimes the best Father’s Day gift isn’t a thing. It’s a day spent together!

From scenic stops and local breweries to ice cream breaks and hidden gems, this family spent Father’s Day exploring our Hops, Hikes & History surprise road trip and had an absolute blast.

If you’re looking for a gift that’s a little different this year, we’ve got you covered.

📸

06/08/2026

The best Father’s Day gifts aren’t always things.

Sometimes they’re backroad stops, random laughs, snack breaks, scenic detours, and a full day of actually spending time together 💌🚗

Surprise Dad with a Guess Where Trip this Father’s Day, no planning required, just pick the trip and let the adventure unfold.

Order by this Thursday (June 11th) to get your gift in time for Father’s Day! ✉️

06/05/2026

We got a little jealous watching you all explore this spring… so we hit the road ourselves 🗺️✨

Small towns, cute stops, unexpected finds, and the kind of day that makes you remember you don’t have to go far to feel like you got away.

The Cheese and Charm Trail understood the assignment 🧀🐐

Address

London, ON
N5V TO N6P

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