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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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Brews, Bites, and Everything Nice
$65 CADThis trip is very true to its name, the coolest brews, the tastiest bites and everything else is very nice.- Accessible
- Kid-Friendly
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Beautifully Haunted
$65 CADThis outdoorsy, story-filled road trip blends spooky legends with beautiful scenery along a rural driving route. A few local eateries and trails are sprinkled throughout the day to keep your energy up while ghost hunting. Most haunted sites are best enjoyed from the outside, so bring your curiosity and imagination to make the ghost stories come alive.- Dog-Friendly
- Kid-Friendly
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Bridges to Beaches
CADPicturesque 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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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!- Accessible
- Dog-Friendly
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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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Backroad Bliss
$65 CADThis trip is perfect for Ottawans, Montrealers, and everyone in between! From waterfalls and a more challenging hike to ridiculously cute towns, shops and restaurants, there is a little bit of everything when you hit the backroads. This trip takes you to great spots in Québec!- Kid-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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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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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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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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Quirky Gems
$65 CADOur best-selling Calgary road trip! Hit the road and visit some quintessential Alberta towns, eat at funky restaurants, support local businesses, and explore picturesque hikes and natural attractions. All without venturing too far from the city!- Accessible
- Kid-Friendly
- Dog-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®! The recipient can then choose a surprise trip that suits them! -
Detour Diaries: Ontario
Regular price $49.00 CADUnit price perThe ultimate travel companion that transforms Ontario's most-travelled highways into unforgettable adventures. -
Hidden Hideaways
$65 CADThis trip is filled with so many hidden gems and charming towns. A countryside brewery or winery, riverside roaming, a seasonal sculpture garden, and unique photo ops galore! This is the perfect trip to do on the way from Ottawa to Montreal. -
Along the River
$39 CADMeander through tiny towns along the river that are brimming with hidden gems. There are countless photo-worthy moments and memories to make on this easygoing scenic road trip.- Accessible
- Kid-Friendly
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Toronto Gems
CADExplore all of the downtown gems in a completely new way. Ditch the car, and walk or bike while you explore what Toronto has to offer. This trip is best for Toronto tourists, those new to the Toronto area, and those who are not super familiar with the Toronto core. The trip has an optional “scavenger hunt" so there is something for you to find and decode at each stop.Sold out -
Whimsical Wonders
$39 CADEscape to hidden gem destinations that make you feel like you've stepped into a fairytale world. Lucious gardens, charming towns and whimsical photo ops make this the perfect road trip.- Kid-Friendly
- Accessible
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Rocky Mountain Route
$65 CADOne of the most iconic road trips in the world with a few secret surprises along the way. Incredible mountain towns, tasty local brews and food and a ton of photo-worthy views! Want to keep going towards Jasper? We included a 'want to keep going' section just in case.- Accessible
- Kid-Friendly
- Dog-Friendly
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Tiny Town Tour
$39 CADMeander along scenic roads while stumbling upon charming tiny towns! This trip has endless photo opportunities, easy outdoor adventures, and plenty of fantastic spots to shop, drink and eat.- Dog-Friendly
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Coastal Crawl
$65 CADGet out of town and feel the ocean breeze in your hair. This trip perfectly combines iconic Nova Scotia views with small town hidden gems.- Kid-Friendly
- Dog-Friendly
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All Things Merry & Bright
$65 CADIf you're looking for a road trip that is full of festivity and holiday cheer, look no further! Meander down decorated streets with a warm beverage in hand, shop for that hard-to-buy-for person at quaint markets, and find your perfect Christmas tree.- Accessible
- Kid-Friendly
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Butter Tarts, Boos & Brews
Regular price $65.00 CADUnit price perEqual parts spooky and cozy, this autumn road trip mixes haunted tales with scenic drives, eerie landmarks, farm markets, local brews, and ooey-gooey butter tarts you’ll be dreaming about all season.- Kid-Friendly
- Accessible
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Winding Roads & Historic Gems
$39 CADDiscover photo-worthy hidden gems along winding roads as you make your way to an iconic road trip destination.- Kid-Friendly
- Dog-Friendly
- Accessible
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Add On: Gift Wrapping
Regular price $14.00 CADUnit price perA reusable gift box with magnetic closure - perfect for presenting their surprise trip and storing souvenirs after the adventure.
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