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/

Quaint towns. Scenic viewpoints. A winery stop. And zero idea where you’re headed 🗺️✨ That’s the magic of All the Pretty...
05/30/2026

Quaint towns. Scenic viewpoints. A winery stop. And zero idea where you’re headed 🗺️✨

That’s the magic of All the Pretty Things! This surprise day trip from Ottawa or Kingston takes you through some of Eastern Ontario’s most charming hidden gems.

Comment “PRETTY” for a link to this trip.🍷🌿

05/29/2026

Done with boring weekends? Same, honestly 👀

A Guess Where Trip turns a “we have nothing to do” Saturday into hidden gems, cute stops, local treats, scenic views, and the best kind of spontaneous adventure.

All the planning is already done. You just open the envelopes and GO. 💌

05/27/2026

Somewhere between Alberta and another planet 👽🏜️

This stop on one of our surprise trips genuinely feels unreal in person. The kind of landscape that makes you stop for a second and go… “wait, this is actually Canada?”

Would you road trip here?

Comment “MARS” and we’ll send you the trip that takes you here 🗺️

05/26/2026

This is what a perfect surprise road trip looks like!
☀️☕️🌲💌

took one of our Vancouver Island surprise road trips and we are OBSESSED with how her day unfolded!

❝I’m usually the planner in my relationship, so having everything mapped out and delivered in those envelopes made the whole experience feel really seamless and fun.❞

Want one near you? Comment “SURPRISE” and we’ll DM you the details

05/25/2026

"Print is dead.”
“Everything is going digital.”
“Don’t waste your money on physical products.”

Meanwhile… we’re still packing surprise road trips by hand every single day ✉️🗺️

Don’t get us wrong, we love our digital trips too. But there’s something about physically opening each envelope, revealing your next stop, and unplugging for a day that just hits DIFFERENT!

A full day out doesn’t have to mean a full-day budget💸 With Groves, Gardens and Grapevines🍇 your day is already planned ...
05/22/2026

A full day out doesn’t have to mean a full-day budget💸
 
With Groves, Gardens and Grapevines🍇 your day is already planned with curated stops, built-in experiences, and plenty to explore along the way.
 
The best part? Each stop can still be super affordable, so you can enjoy the mystery, the memories, and the adventure without feeling like you accidentally planned a $300 day!
 
Ready to see how far a Guess Where Trips day can take you?
📍 Groves, Gardens and Grapevines is waiting!

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London, ON
N5V TO N6P

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