How does it work?
Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.
See our road trips below, or check out our quiz and trip map to help find your perfect adventure.
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Local Markets and Picturesque Towns
$65 USDOne of our best-selling trips, and for good reason. Stops include historic towns, local markets, eateries, and hidden gems - all of which feel especially lovely when winter slows things down. This trip makes a great gift thanks to its versatility.- Accessible
- Kid-Friendly
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An Adventure is Brewing
$65 USDThis road trip takes you on the perfect summer adventure filled with lavender fields, funky hidden gems, beaches and unique wineries and breweries. This is our featured summer trip and is best taken mid-May to early-October!- Accessible
- Dog-Friendly
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The Small Town Charm Trail
$65 USDYou know those towns that are described as “blink-and-you’ll-miss-it”? They often have the most amazing hidden gems - especially when winter slows things down and the crowds thin out. Get to know a few cozy pockets of Ontario with this surprise road trip.- Accessible
- Kid-Friendly
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Road Trip Gift Card
Regular price $74.00 USDUnit price perGive the gift of a one-day surprise road trip with Guess Where Trips®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire.
Set off from London and uncover the hidden gems of Southwestern Ontario. Each surprise destination offers something unique, all within a short drive. Whether you're delving into quirky local history, exploring scenic trails, or finding that perfect café, London is your ideal launchpad. Pack your curiosity, hit the road, and create lasting memories on your next Ontario adventure!