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

  • FATHER'S DAY PICK
    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
  • GREAT OVERNIGHT GETAWAY
    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
  • BEST SELLER
    Local Markets & Picturesque Towns

    Local Markets & 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
  • FATHER'S DAY PICK
    Hops, Hikes & History

    Hops, Hikes & History

    $65 USD
    There is so much more to this trip than the name implies. From hidden local breweries to unique trails and scenic sights, this trip will take you to a few unknown areas that you’re sure to love!
    • Kid-Friendly
    • 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
    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
  • FATHER'S DAY PICK
    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 USD
    This trip is very true to its name...the coolest brews, the tastiest bites and everything else is very nice. This itinerary has it all and is not too far from the city.
    • 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
  • BEST SELLER
    Patio table filled with beers.

    An Adventure is Brewing

    $65 USD
    A summer road trip within driving distance of Toronto, Hamilton, Kitchener, and London with beaches, wineries, and hidden gems.
    • Accessible
    • Dog-Friendly
  • BEST SELLER
    Woman looking out of car window.

    All the Pretty Things

    $65 USD
    A scenic road trip from Ottawa or Kingston with charming stops, historic sites, and wineries.
    • 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!