Guess Where Trips
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We're Guess Where Trips 👋🏻 and we plan one-day self-guided surprise road trips across Canada and the USA! 🇨🇦🇺🇸
No planning needed.
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.
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 💘🚗
06/11/2026
Our trips are the perfect Father’s Day gift; quality time, new adventures, and moments your family will talk about for years.
Order before midnight tonight to guarantee delivery in time for the 21st.
Top Trips for Dad: https://guesswheretrips.com/pages/road-trip-map?tags=dad%27s+picks
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 🧀🐐
06/02/2026
Dad + kids + surprise envelopes = the best Father’s Day ever 🚗✨
June 21st is closer than you think! 👀
Find a trip near you: https://guesswheretrips.com/pages/road-trip-map
Click here to claim your Sponsored Listing.
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Website
Address
London, ON
N5V TO N6P
