Woman holding four Guess Where Trips envelopes while on road trip

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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.

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  • FABULOUS WINTER TRIP!
    Escape to Nature

    Escape to Nature

    $65 CAD
    Explore 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
  • BEST SELLER
    Woman looking out of car window.

    All the Pretty Things

    $65 CAD
    Take in all the pretty views and things on this picturesque trip. The itinerary is packed with stunning viewpoints, historic attractions and delicious restaurants and wineries.
    • Kid-Friendly
  • BEST DONE SPRING TO FALL
    Woman holding hands with small child on the beach in front of the ocean.

    From Country to Coast

    $49 CAD Sale
    Meander along country roads, explore waterfall wonders, local wineries, 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
    Sale
  • BEST SELLER
    A group of people toasting with glasses of beer and wine at a social gathering, with blurred faces for privacy.

    Brews, Bites, and Everything Nice

    $65 CAD
    This trip is very true to its name - the coolest brews, the tastiest bites, and everything else is very nice. With cozy stops and short scenic drives, this itinerary has it all and isn’t too far from the city.
    • Accessible
    • Kid-Friendly
  • 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
  • SCENIC ROUTE
    Spooky black and white photo of a road on a foggy day.

    Beautifully Haunted

    $49 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 SUMMER TRIP!
    Sister and brother hugging on a boardwalk.

    Bridges to Beaches

    $49 CAD Sale
    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
    Sale
  • BEST SELLER
    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
  • 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 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

    $49 CAD Sale
    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
    Sale
  • SCENIC ROUTE
    Historic white house underneath a vibrant blue sky.

    Hidden Gems of Huronia

    $49 CAD Sale
    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
    Sale
  • BEST SELLER
    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
    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
  • Which Way? A Surprise Road Trip Card Game

    Which Way? A Surprise Road Trip Card Game

    Regular price $22.00 CAD
    A surprise road trip game where the entire point is to get lost!
  • Road Trip Tote Bag

    Road Trip Tote Bag

    Regular price $15.00 CAD
    An essential locally made tote bag for your road trip ahead. Carry everything from your surprise package to all the snacks and goodies you'll pick up throughout your day.
  • 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.
  • BEST DONE SPRING-FALL
    Lighthouse overlooking the water

    Curiosities & Coastlines

    $49 CAD Sale
    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
    Sale
  • BEST SELLER
    River running through forest.

    Along the River

    $65 CAD
    Meander 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
  • Road Trip Game Pack

    Road Trip Game Pack

    Regular price $12.00 CAD
    Keep the young ones busy with a fun game pack to play with on the road! Dozens of games and activities to keep kids of all ages entertained.
  • 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 SELLER
    Whimsical Wonders

    Whimsical Wonders

    $65 CAD
    Escape 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
  • BEST SELLER
    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
  • BEST SELLER
    Hudson River Hideaways

    Hudson River Hideaways

    $65 CAD
    An iconic road trip route with a twist. Along the Hudson, you’ll uncover hidden hideaways like crumbling ruins, quiet riverside towns, atmospheric cemeteries, and plenty of scenic surprises along the way
    • Dog-Friendly
Three women walking through tulip fields
Winding roads through mountains at sunrise

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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!