Ontario Road Trips
Select a trip that works with your driving and travel preferences. If it's hard to choose, take our road trip quiz instead.
Browse all trips
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Detour Diaries: Ontario
Regular price $59.00 CADUnit price perPacked with 500+ of our favourite road trip stops across Ontario, Detour Diaries features 130+ detailed, user-friendly maps and over 300 pages organized by major highways to make planning effortless. You’ll also get bonus QR code access to an interactive mobile map for easy navigation on the go.
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Toronto Play Day Passport
Regular price $59.00 CADUnit price perDiscover fully planned, kid-friendly days out across Toronto and the GTA. Just scratch a card to reveal a complete outing - with a destination, bonus stops, food spots, and tips all figured out for you. -
The Cheese & Charm Trail
$65 CADCalling 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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Road Trip Gift Card
Regular price $74.00 CADUnit 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. -
Curiosities & Coastlines
$65 CADWander through eerie ruins, stop at offbeat roadside finds, explore historic small towns, and relax by the shores of Lake Huron. This laid-back Bruce County adventure perfectly mixes local legends, great eats, and scenic spots!- Kid-Friendly
- Dog-Friendly
- Accessible
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The Sweet & Scenic Route
$65 CADA little sweet, a little scenic - this road trip blends cozy cafés, local wines, and maple treats with easy trails, waterfalls, and serene ponds. Perfect for a girls' getaway or a romantic day trip! *Note that this trip can be taken in the summer months; however, the waterfalls may slow to a trickle in the hot weather!- Accessible
- Dog-Friendly
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Bayside Wonders
$65 CADThe perfect blend of charming small towns, farmers markets, and wine tastings mixed with epic waterfalls and a couple unique trails. Bayside Wonders is a bit further, which makes for an incredible weekend getaway! Please note: A few recommendations have been moved from The Waterfall Route to this new trip. There are still tons of new spots to explore!- Kid-Friendly
- Dog-Friendly
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Gardens, Trails & Local Ales
$65 CADIf you're into hidden gem breweries and easy outdoor adventures that are close to home, then this is the trip for you! We've also sprinkled in a few bakeries to satisfy your sweet tooth, quirky shops, and some local history throughout the day.- Kid-Friendly
- Accessible
- Dog-Friendly
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Hidden Gems of Huronia
$65 CADDiscover the endless charm of a lesser-known area that is full of haunted history, picturesque trails, cute small towns and farm-fresh flavours. We're sure you'll want to keep coming back for years to come!- Kid-Friendly
- Accessible
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From Country to Coast
$65 CADMeander 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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Muskoka Meandering
$65 CADMuskoka Meandering is the perfect way to escape from the hustle and bustle of the city and immerse yourself in nature while enjoying delicious wines and beers, beautiful scenery and lookouts, and charming small towns.- Kid-Friendly
- Dog-Friendly
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Escape to Nature
$65 CADExplore tiny towns and easy outdoor adventures before cozying up at a local cafe or brewery. Optional wintery activities include ice skating and snowshoeing! Please note: this trip is similar to the Sport Chek Winter Trek for Toronto.- Kid-Friendly
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Riverside Roaming
$65 CADStart 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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Funky Florals and Fine Wines
$65 CADThis pretty little road trip offers quite a few hidden gems combined with a few iconic attractions. Must enjoy: wine, food and flowers.- Accessible
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Wine Time and Hidden Gems
$65 CADCraving rolling vineyard views, artful little towns, farm markets and that breezy, laid-back feel only lakeside moments can deliver? This is the trip for you! It’s the kind of place that deserves more than a quick visit...make it a weekend if you can!- Dog-Friendly
- Accessible
- Kid-Friendly
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Weird & Wonderful Things
$65 CADThis road trip takes you north towards beautiful sights, unusual attractions and secluded waterfalls.- Kid-Friendly
- Dog-Friendly
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Vistas & Caves
$65 CADThis road trip is a quick jaunt north of Toronto and is perfect for the outdoor enthusiast. It really is the perfect mix of everything.- Accessible
- Kid-Friendly
- Dog-Friendly
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Views & Secret Stops
$65 CADViews for days and a scenic route that will take you there. This trip is perfect for anyone who's up for a more active day (but the views are worth it!).- Kid-Friendly
- Dog-Friendly
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Toronto Gems
Regular price $39.00 CADUnit 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 Whimsical Route
$65 CADGet ready for a road trip where nature, history, hidden gems, and a touch of cinematic magic come together for a perfectly whimsical escape just outside the city!- Kid-Friendly
- Accessible
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The Waterfall Route
$65 CADExplore a variety of waterfalls, charming towns, funky restaurants and several photo ops throughout the day! This trip is perfect for spring - fall travellers. Waterfalls may dry up in extreme heat.- Kid-Friendly
- Dog-Friendly
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The Small Town Charm Trail
$65 CADYou 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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Taste of the Country
$65 CADThis trip is just a short jaunt from Toronto and is perfect for foodies and families! You'll explore incredible farmers markets, cute small towns, a few local spots to grab a drink and an easy wooded trail.- Accessible
- Kid-Friendly
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Southern Express
$65 CADThink 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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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!
