Parent and child opening a Guess Where Trips booklet on a picnic bench

Day Trips from the Toronto Area

Pick a trip that fits your driving and travel style. Can't decide? Take our road trip quiz to find the best Toronto day trip for you! No matter the season, you’ll find a one-day surprise adventure in or around the GTA that’s sure to leave you with unforgettable memories.

How does it work?

Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.

See our road trips below, or check out our quiz and trip map to help find your perfect adventure.

  • Toronto Play Day Passport

    Toronto Play Day Passport

    $59.00 CAD
    Discover fully planned, kid-friendly days out across Toronto and the GTA. Just scratch a card to reveal a complete outing - with a destination, bonus stops, food spots, and tips all figured out for you.
    Can depart from: Toronto Area, GTA
  • Detour Diaries: Ontario

    Detour Diaries: Ontario

    $59.00 CAD

    Packed with 500+ of our favourite road trip stops across Ontario, Detour Diaries features 130+ detailed, user-friendly maps and over 300 pages organized by major highways to make planning effortless. You’ll also get bonus QR code access to an interactive mobile map for easy navigation on the go.

  • Road Trip Gift Card

    Road Trip Gift Card

    $74.00 CAD
    Give the gift of a one-day surprise road trip with Guess Where Trips®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire.
  • MOTHER'S DAY PICK
    Local Markets & Picturesque Towns

    Local Markets & Picturesque Towns

    $65 CAD
    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
    Can depart from: London Area, Toronto Area
  • MOTHER'S DAY PICK
    Patio table filled with beers.

    An Adventure is Brewing

    $65 CAD
    A summer road trip within driving distance of Toronto, Hamilton, Kitchener, and London with beaches, wineries, and hidden gems.
    • Accessible
    • Dog-Friendly
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area
  • STAFF PICK
    A person walking on a trail surrounded by tall trees

    Vistas & Caves

    $65 CAD
    This road trip is a quick jaunt north of Toronto and is perfect for the outdoor enthusiast. It really is the perfect mix of everything.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area, Barrie Area
  • BEST SELLER
    Weird & Wonderful Things

    Weird & Wonderful Things

    $65 CAD
    This road trip takes you north towards beautiful sights, unusual attractions and secluded waterfalls.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Toronto Area, Kitchener-Waterloo Area, Kingston Area, Barrie Area
  • GREAT FOR YOUNG FAMILIES
    Alpaca behind a fence, being fed a carrot.

    Country Farms & Furry Friends

    $65 CAD
    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
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area
  • STAFF PICK
    Bikes parked in front of a flower shop.

    Funky Florals and Fine Wines

    $65 CAD
    This pretty little road trip offers quite a few hidden gems combined with a few iconic attractions. Must enjoy: wine, food and flowers.
    • Accessible
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area
  • BEST SELLER
    Water reflecting forest and blue sky.

    Muskoka Meandering

    $65 CAD
    Muskoka Meandering is the perfect way to escape from the hustle and bustle of the city and immerse yourself in nature while enjoying delicious wines and beers, beautiful scenery and lookouts, and charming small towns.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Kitchener-Waterloo Area, Toronto Area, Barrie Area
  • MOTHER'S DAY PICK
    Woman sitting on a rocky shore overlooking a river.

    Riverside Roaming

    $65 CAD
    Start your day in a picture-perfect town by the river before strolling along boardwalks, dining at a funky distillery, indulging at farm shops and so much more. This trip is a nice distance from the city and can be done year-round!
    • Kid-Friendly
    • Accessible
    Can depart from: Toronto Area, London Area, Kitchener-Waterloo Area
  • GREAT OVERNIGHT GETAWAY
    Markets to Mountains

    Markets to Mountains

    $65 CAD
    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
    Can depart from: Kitchener-Waterloo Area, Toronto Area, London Area, Barrie Area
View all