Woman holding four Guess Where Trips envelopes while on road trip

All Canada

Select a trip that works with your driving and travel preferences. If it's hard to choose, take our road trip quiz instead.

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  • SCENIC ROUTE
    Spooky black and white photo of a road on a foggy day.

    Beautifully Haunted

    Regular price $65.00 Sale price $39.00 CAD
    Sale
    This 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
    Sale
  • PERFECT WINTER ROAD TRIP!
    The Sweet & Scenic Route

    The Sweet & Scenic Route

    $65 CAD
    A little sweet, a little scenic - this road trip blends cozy cafés, local wines, and maple treats with easy trails, frozen waterfalls, and snow-covered streets. Perfect for a girls' getaway or a romantic day trip!
    • Accessible
    • Dog-Friendly
  • PERFECT SUMMER TRIP!
    Sister and brother hugging on a boardwalk.

    Bridges to Beaches

    $65 CAD
    Picturesque 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
  • CAN BE DONE IN WINTER
    The Whimsical Route

    The Whimsical Route

    $65 CAD
    Get 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
  • BEST SELLING GIFT
    Woman taking a photo from the passenger seat of a car.

    Backroad Bliss

    $65 CAD
    This 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
  • Best done spring-fall
    Southern Express

    Southern Express

    $65 CAD
    Think 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
  • GREAT WEEKEND GETAWAY
    Two women on a beach looking out at the water

    Bayside Wonders

    $65 CAD
    The 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
  • SCENIC ROUTE
    Historic white house underneath a vibrant blue sky.

    Hidden Gems of Huronia

    $65 CAD
    Discover 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
  • best done spring-fall
    Views & Secret Stops

    Views & Secret Stops

    $65 CAD
    Views 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
  • BEST SELLING GIFT
    Quirky Gems

    Quirky Gems

    $65 CAD
    Our 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
  • BEST DONE SPRING-FALL
    Hidden Hideaways

    Hidden Hideaways

    $65 CAD
    This 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.
  • ONTARIO
    All Things Merry & Bright

    All Things Merry & Bright

    Regular price $65.00 Sale price $39.00 CAD
    Sale
    If 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
    Sale
  • PERFECT OVERNIGHT GETAWAY
    Lighthouse overlooking the water

    Curiosities & Coastlines

    $65 CAD
    Wander 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
  • FABULOUS OVERNIGHT TRIP
    Rocky Mountain Route

    Rocky Mountain Route

    $65 CAD
    One of the most iconic road trips in the world, with a few secret surprises along the way. Think snow-dusted mountain towns, tasty local brews and food, and no shortage of jaw-dropping views. Want to keep going toward Jasper? We’ve included extra suggestions at the fourth stop, just in case.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLING GIFT
    Maritime boats and boathouses.

    Coastal Crawl

    $65 CAD
    Get 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
  • CLOSE TO OTTAWA
    Workers filling up a glasses of beer at a brewery

    Gardens, Trails & Local Ales

    Regular price $65.00 Sale price $39.00 CAD
    Sale
    If 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
    Sale
  • BEST SELLING GIFT
    The Taste Trail

    The Taste Trail

    $65 CAD
    This road trip will take you to some funky eateries, family farms, wineries, cideries, and a whole lot more. To offset the treats, we've included a few whimsical hikes to end your day.
    • Accessible
  • best done spring-fall
    Quintessential Québec

    Quintessential Québec

    $65 CAD
    Gorgeous drives, picturesque towns, historic hikes, phenomenal food and so much more. You'll quickly fall in love with the area and want to come back again and again.
    • Dog-Friendly
    • Kid-Friendly
  • BEST DONE SPRING - FALL
    Woman standing in front of a waterfall.

    Chasing Waterfalls

    $65 CAD
    Don't let TLC lead you astray. You should definitely go chasing waterfalls! This trip is jam-packed with good food, picturesque waterfalls, and quirky gems.
    • Dog-Friendly
  • CAN BE DONE IN WINTER
    Rural Adventures

    Rural Adventures

    $65 CAD
    Scenic driving routes, a ton of photo-worthy views and rural, small town vibes await you on this surprise road trip.
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
  • GREAT SUMMER ROADTRIP
    Peculiar Wonders

    Peculiar Wonders

    $65 CAD
    Travel through time and terrain on this Alberta road trip packed with scenic strolls, quirky museums, epic photo ops, and fun for all ages. From lush gardens and lakeside boardwalks to towering trestle bridges and even free-roaming bison, this one's full of "wait, where are we?" moments—in the best way possible.
    • Kid-Friendly
    • Dog-Friendly
  • BEST DONE SPRING-FALL
    Valley Views

    Valley Views

    $65 CAD
    Down in the valley where the green grass grows...you'll find charming towns, get lost in lush vineyards, take in vast views and hike scenic trails on this countryside road trip.
    • Dog-Friendly
    • Kid-Friendly
  • An iconic winter route
    A scenic view of a road leading towards mountains with green trees on both sides.

    Secrets on the Scenic Route

    $65 CAD
    This trip blends iconic attractions with quite a few hidden gems before ending in one of the coolest villages in Canada. Snowy peaks, misty views, and quieter stops make this famous route feel extra special when explored at a slower pace.
    • Dog-Friendly
  • BEST DONE JUNE-SEPTEMBER
    The Long and Unknown Road

    The Long and Unknown Road

    $65 CAD
    If you love a long and interesting drive, this trip is for you! This trip is approximately 5 hours round-trip from Calgary, so we recommend leaving super early or extending your stay into an overnight getaway.
    • Dog-Friendly
Three women walking through tulip fields
Winding roads through mountains at sunrise

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