Woman holding four Guess Where Trips envelopes while on road trip

Our 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

  • PERFECT SUMMER TRIP!
    Sister and brother hugging on a boardwalk.

    Bridges to Beaches

    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
    Sold out
  • 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
  • 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
  • HIDDEN GEMS
    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
  • 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
  • GREAT FALL TRIP
    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
  • HIDDEN GEMS IN THE NIAGARA REGION
    Couple holding hands on a forest trail

    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, waterfalls, and serene ponds. Perfect for a girls' getaway or a romantic day trip!
    • Accessible
    • Dog-Friendly
  • BEST SELLER
    Quirky Gems

    Quirky Gems

    $65 CAD
    Our best-selling trip from Calgary! 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.
  • scavenger hunt included
    Toronto Gems

    Toronto Gems

    CAD
    Explore 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
  • BEST SELLER
    River running through forest.

    Along the River

    $39 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
  • BEST SELLER
    Whimsical Wonders

    Whimsical Wonders

    $39 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
  • AN ICONIC ROUTE
    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. 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
  • BEST SELLER
    Tiny Town Tour

    Tiny Town Tour

    $39 CAD
    Meander 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
  • 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
  • GREAT FALL TRIP
    Winding Roads & Historic Gems

    Winding Roads & Historic Gems

    $39 CAD
    Discover photo-worthy hidden gems along winding roads as you make your way to an iconic road trip destination.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • BEST SELLER
    Hudson River Hideaways

    Hudson River Hideaways

    $39 CAD
    An iconic road trip route with a twist! We've found countless hidden hideaways along the Hudson including; crumbling ruins, quaint towns, spooky cemeteries and more.
    • Dog-Friendly
  • BEST SELLER
    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
  • CLOSE TO OTTAWA
    Workers filling up a glasses of beer at a brewery

    Gardens, Trails & Local Ales

    $65 CAD
    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
  • 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
  • CAN BE DONE YEAR-ROUND
    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
  • PERFECT YEAR-ROUND
    Haunts, Hikes & History

    Haunts, Hikes & History

    $39 CAD
    From haunted happenings to easy strolls and historic hot spots, this trip has a little bit of everything for everyone!
    • Kid-Friendly
    • Dog-Friendly
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

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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!