Woman holding four Guess Where Trips envelopes while on road trip

Only 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

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

    Beautifully Haunted

    $39 USD
    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
  • BEST DONE MAY-OCTOBER
    Sister and brother hugging on a boardwalk.

    Bridges to Beaches

    $65 USD
    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
  • HIDDEN GEMS
    The Whimsical Route

    The Whimsical Route

    $65 USD
    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
    A boardwalk leading to a beach with the sun shining brightly in the sky.

    Southern Express

    $65 USD
    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 SELLER
    Woman taking a photo from the passenger seat of a car.

    Backroad Bliss

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

    Bayside Wonders

    $65 USD
    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
  • best done spring-fall
    A scenic view of a body of water with trees on the banks under a clear sky.

    Views & Secret Stops

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

    Hidden Gems of Huronia

    $65 USD
    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
  • PERFECT OVERNIGHT GETAWAY
    Lighthouse overlooking the water

    Curiosities & Coastlines

    $65 USD
    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 DONE SPRING-FALL
    Hidden Hideaways

    Hidden Hideaways

    $65 USD
    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.
  • FATHER'S DAY PICK
    Workers filling up a glasses of beer at a brewery

    Gardens, Trails & Local Ales

    $65 USD
    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
  • Digital Download Only
    Aerial view of Toronto cityscape during sunset, showcasing various buildings and the CN Tower.

    Toronto Gems

    Regular price $39.00 USD
    Explore 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!
  • best done spring-fall
    Quintessential Québec

    Quintessential Québec

    $65 USD
    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
    Sale
  • NEW SUMMER ROAD TRIP!
    Cheese shop photographed from doorway.

    The Cheese & Charm Trail

    $65 USD
    Calling 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
Three women walking through tulip fields
Winding roads through mountains at sunrise

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