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 ...
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The Guess Where Trips Blog
Check out what we've been up to, what we're looking forward to, and how we make the road trips you know and love.
From the Founder: How I Plan the Perfect Vacation
When it comes to my own vacations, I don’t wing it. I use a spreadsheet system to compare options side-by-side and make confident decisions (continue reading on to get access...
From the Founder: How I Plan the Perfect Vacation
When it comes to my own vacations, I don’t wing it. I use a spreadsheet system to compare options side-by-side and make confident decisions (continue reading on to get access...
Meet the Founder
How I Started Guess Where Trips If you’ve ever opened one of our trips and thought “this is such a fun idea, how did this even start?”… you’re not alone....
Meet the Founder
How I Started Guess Where Trips If you’ve ever opened one of our trips and thought “this is such a fun idea, how did this even start?”… you’re not alone....
We Were on NBC's 'New York Live'!
Ever wondered how a perfect road trip comes together? Go behind the scenes to see how each Guess Where Trip is researched, tested, and thoughtfully designed.
We Were on NBC's 'New York Live'!
Ever wondered how a perfect road trip comes together? Go behind the scenes to see how each Guess Where Trip is researched, tested, and thoughtfully designed.
How We Plan the Perfect Road Trip
Ever wondered how a perfect road trip comes together? Go behind the scenes to see how each Guess Where Trip is researched, tested, and thoughtfully designed.
How We Plan the Perfect Road Trip
Ever wondered how a perfect road trip comes together? Go behind the scenes to see how each Guess Where Trip is researched, tested, and thoughtfully designed.
10 Things to Do in Cold Spring, NY: The Best Da...
As road trip experts, we know that the best small towns have a little bit of everything. That’s why Cold Spring, NY needs to be on your radar! Whether you...
10 Things to Do in Cold Spring, NY: The Best Da...
As road trip experts, we know that the best small towns have a little bit of everything. That’s why Cold Spring, NY needs to be on your radar! Whether you...
10 Things to Do in Stratford, ON for a Charming...
As road trip experts with a soft spot for storybook small towns, Stratford, Ontario is exactly the kind of place we love to send travellers. Below is our list of...
10 Things to Do in Stratford, ON for a Charming...
As road trip experts with a soft spot for storybook small towns, Stratford, Ontario is exactly the kind of place we love to send travellers. Below is our list of...
