Browse all trips
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Local Markets & Picturesque Towns
$65 USDOne of our best-selling trips, and for a good reason. Stops include historic towns, local markets, eateries and hidden gems. This trip makes a great gift because of its versatility.- Accessible
- Kid-Friendly
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An Adventure is Brewing
$65 USDA summer road trip within driving distance of Toronto, Hamilton, Kitchener, and London with beaches, wineries, and hidden gems.- Accessible
- Dog-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. -
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! Get to know a few small pockets of Ontario with this surprise road trip.- Accessible
- Kid-Friendly
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Country Farms & Furry Friends
$65 USDAlpacas, donkeys and goats - oh my! Start your day off at a funky country market, before hanging with the birds and ending the day with some furry friends.- Kid-Friendly
- Accessible
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Riverside Roaming
$65 USDStart your day in a picture-perfect town by the river before strolling along boardwalks, dining at a funky distillery, indulging at farm shops and so much more. This trip is a nice distance from the city and can be done year-round!- Kid-Friendly
- Accessible
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Hops, Hikes & History
$65 USDThere is so much more to this trip than the name implies. From hidden local breweries to unique trails and scenic sights, this trip will take you to a few unknown areas that you’re sure to love!- Kid-Friendly
- Dog-Friendly
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Secrets in the South
$65 USDWith funky markets, scenic roads and the most picturesque towns, you'll love all of the secrets you discover on the road. This trip is best enjoyed between June - September as there are a handful of fabulous seasonal suggestions.- Kid-Friendly
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From Country to Coast
$65 USDMeander along country roads, explore waterfall wonders, & visit local breweries, farm shops, and beachside towns. This trip has something for everyone, from families to girlfriend getaways and seniors, you’ll find several hidden gems along the way.- Kid-Friendly
- Dog-Friendly
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Bridges to Beaches
$65 USDPicturesque bridges to sandy beaches and everything in between. This trip takes you off the beaten path to some of our favourite places in Ontario.- Accessible
- Kid-Friendly
- Dog-Friendly
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Southern Express
$65 USDThink cozy bakeries, swim spots, easy hikes, and wine with a view, all wrapped up in one charming escape. You’ll wonder how this area stayed off your radar for so long!- Kid-Friendly
- Dog-Friendly
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Toronto Gems
Regular price $39.00 USDUnit price perExplore all of Toronto's downtown gems in a completely new way - ditch the car and walk or bike while you explore! This trip is best for anyone who isn't super familiar with the Toronto core, plus there's an optional “scavenger hunt" so there is something for you to find and decode at each stop! -
The Cheese & Charm Trail
$65 USDCalling all cheese lovers and countryside explorers! This deliciously charming road trip winds through scenic backroads filled with flower farms, local markets, dairy stops, and small-town surprises - perfect for a day of snacking, wandering, and saying “just one more stop".- Accessible
- Kid-Friendly
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Gift-a-Trip
The ultimate present for the avid traveller. Select a digital or mailed 'Gift-A-Trip' option that covers the full cost of one of our road trips. We promise you this will be one of the most memorable and unique gifts they'll ever receive!