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

  • HIDDEN GEMS IN THE NIAGARA REGION
    The Sweet & Scenic Route

    The Sweet & Scenic Route

    $65 USD
    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
  • MOTHER'S DAY PICK
    Bayside Wonders

    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
  • MOTHER'S DAY PICK
    Gardens, Trails & Local Ales

    Gardens, Trails & Local Ales

    $65 USD
    If you're into hidden gem breweries and easy outdoor adventures 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
  • SCENIC ROUTE
    Hidden Gems of Huronia

    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
    • Dog-Friendly
  • MOTHER'S DAY PICK
    From Country to Coast

    From Country to Coast

    $65 USD
    Meander along country roads, explore waterfall wonders, local wineries, breweries, farm shops, and beachside towns. This trip has something for everyone, from families to girlfriend getaways and seniors, you’ll find several hidden gems along the way.
    • Kid-Friendly
    • Dog-Friendly
  • SCENIC ROUTE
    Spooky black and white photo of a road on a foggy day.

    Beautifully Haunted

    $55 USD Sale
    This outdoorsy road trip is full of spooky spots set along a picturesque driving route. You'll definitely want to read all of the haunted stories to make the most of the day! A few local eateries and trails are sprinkled throughout the day to keep your energy up while ghost hunting.
    • Dog-Friendly
    • Kid-Friendly
    Sale
  • BEST SELLER
    Muskoka Meandering

    Muskoka Meandering

    $65 USD
    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
  • GREAT YEAR-ROUND TRIP
    Escape to Nature

    Escape to Nature

    $65 USD
    Explore tiny towns and easy outdoor adventures before cozying up at a local cafe or brewery. Optional wintery activities include ice skating and snowshoeing! Please note: this trip is similar to the Sport Chek Winter Trek for Toronto.
    • Kid-Friendly
  • MOTHER'S DAY PICK
    Riverside Roaming

    Riverside Roaming

    $65 USD
    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
  • STAFF PICK
    Funky Florals and Fine Wines

    Funky Florals and Fine Wines

    $65 USD
    This pretty little road trip offers quite a few hidden gems combined with a few iconic attractions. Must enjoy: wine, food and flowers.
    • Accessible
  • MOTHER'S DAY PICK
    Wine Time and Hidden Gems

    Wine Time and Hidden Gems

    $65 USD
    Craving rolling vineyard views, artful little towns, farm markets and that breezy, laid-back feel only lakeside moments can deliver? This is the trip for you! It’s the kind of place that deserves more than a quick visit...make it a weekend if you can!
    • Dog-Friendly
    • Accessible
    • Kid-Friendly
  • BEST SELLER
    Weird and Wonderful Things

    Weird and Wonderful Things

    $65 USD
    This road trip takes you north towards beautiful sights, unusual attractions and secluded waterfalls.
    • Kid-Friendly
    • Dog-Friendly
  • BEST DONE spring-fall
    Waterfront Wonders

    Waterfront Wonders

    USD
    We've recommended an incredibly scenic route that takes you to a variety of picturesque stops you'll fall in love with. The best part? There are hardly any crowds.
    • Kid-Friendly
    • Dog-Friendly
    Sold out
  • GREAT YEAR-ROUND TRIP
    Vistas & Caves

    Vistas & Caves

    $65 USD
    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
  • best done spring-fall
    Views & Secret Stops

    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
  • scavenger hunt included
    Toronto Gems

    Toronto Gems

    $65 USD
    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.
  • FAMILY FRIENDLY
    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
    • Dog-Friendly
  • Best done spring-fall
    The Waterfall Route

    The Waterfall Route

    $65 USD
    Explore a variety of waterfalls, charming towns, funky restaurants and several photo ops throughout the day! This trip is perfect for spring - fall travellers. Waterfalls may dry up in extreme heat.
    • Kid-Friendly
    • Dog-Friendly
  • STAFF PICK
    The Small Town Charm Trail

    The Small Town Charm Trail

    $65 USD
    You know those towns that are described as 'blink-and-you'll-miss-it'? They often have the most amazing hidden gems! Get to know a few small pockets of Ontario with this surprise road trip.
    • Accessible
    • Kid-Friendly
  • The Fairy Tale Trail

    The Fairy Tale Trail

    USD
    This 'mini' trip is designed for families with children under 12. The variety of stroller-friendly and toddler-friendly activities make it a no-fuss day for everyone in the car. We've even included scavenger-style activities throughout the itinerary to keep your kids engaged.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
    Sold out
  • BEST SELLER
    Taste of the Country

    Taste of the Country

    $65 USD
    This trip is just a short jaunt from Toronto and is perfect for foodies and families! You'll explore incredible farmers markets, cute small towns, a few local spots to grab a drink and an easy wooded trail.
    • Accessible
    • Kid-Friendly
  • Optional Scavenger Hunt Included
    Spooky Sights & Ghostly Tales

    Spooky Sights & Ghostly Tales

    $65 USD
    Spooky ruins, abandoned buildings, and haunted mansions make up this ghostly road trip. Perfect for history buffs & paranormal seekers! We've even included a fun scavenger hunt! This trip takes place in a busier city, so travellers may run into some traffic.
    • Dog-Friendly
  • Best done spring-fall
    Southern Express

    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
  • MOTHER'S DAY PICK
    Secrets in the South

    Secrets in the South

    $65 USD
    With funky markets, scenic roads and the most picturesque towns, you'll love all of the secrets you discover on the road. This trip is best enjoyed between June - October as there are a handful of fabulous seasonal suggestions.
    • Kid-Friendly
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

Take Our Quiz to Find Out

Select your region and interests to find the best trip for you.

Take the Quiz
Woman on road trip leaning out window

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!