Woman holding four Guess Where Trips envelopes while on road trip

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

  • 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
  • BEST SELLER
    Outdoor Adventures & Scenic Roads

    Outdoor Adventures & Scenic Roads

    $65 USD
    Outdoor Adventures encompasses everything you could possibly want in a road trip getaway. Scenic roads, cool attractions and good food!
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • CAN BE DONE YEAR-ROUND
    Markets to Mountains

    Markets to Mountains

    $65 USD
    From cute markets to mountainside hikes, Markets to Mountains provides you with all the stops for a cozy yet adventurous day trip in Ontario. We highly recommend booking a hotel at the finishing stop for the ultimate weekend getaway.
    • Kid-Friendly
    • Accessible
  • MOTHER'S DAY PICK
    Woman looking at plants at a market.

    Local Markets and Picturesque Towns

    $65 USD
    One of our best-selling trips, and for a good reason. Stops include historic towns, local markets, eateries and hidden gems. This trip makes a great gift because of its versatility.
    • Accessible
    • Kid-Friendly
  • Best done spring-fall
    Hops, Hikes & History

    Hops, Hikes & History

    $65 USD
    There is so much more to this trip than the name implies. This itinerary will take you to a number of unknown areas you'll fall in love with. The hops, hikes and history are just the added perks.
    • Kid-Friendly
    • Dog-Friendly
  • CAN BE DONE YEAR-ROUND
    Historic Haunts

    Historic Haunts

    $65 USD
    If you're a fan of ghost stories and unusual attractions, this trip is for you! We've rounded up the spookiest attractions for a 'Haunted History' route. Please Note: This trip takes place in the same area as Local Markets & Picturesque Towns.
    • Accessible
    • Dog-Friendly
  • 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.
  • GREAT FOR YOUNG FAMILIES
    Alpaca behind a fence, being fed a carrot.

    Country Farms & Furry Friends

    $65 USD
    Alpacas, donkeys and goats - oh my! Start your day off at a funky country market, before hanging with the birds and ending the day with some furry friends.
    • Kid-Friendly
    • Accessible
  • MOTHER'S DAY PICK
    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
  • BEST SELLER
    Brews, Bites, and Everything Nice

    Brews, Bites, and Everything Nice

    $65 USD
    This trip is very true to its name, the coolest brews, the tastiest bites and everything else is very nice.
    • Accessible
    • Kid-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
  • MOTHER'S DAY PICK
    Patio table filled with beers.

    An Adventure is Brewing

    $65 USD
    This road trip takes you on the perfect summer adventure filled with lavender fields, funky hidden gems, beaches and unique wineries and breweries. This is our featured summer trip and is best taken mid-May to early-October!
    • Accessible
    • Dog-Friendly
  • MOTHER'S DAY PICK
    Woman looking out of car window.

    All the Pretty Things

    $65 USD
    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.
    • Accessible
    • Dog-Friendly
    • Kid-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!