Woman holding four Guess Where Trips envelopes while on road trip

Home - Eastern CA

Select a trip that works with your driving and travel preferences. If it's hard to choose, take our road trip quiz instead.

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  • Best done spring-fall
    A boardwalk leading to a beach with the sun shining brightly in the sky.

    Southern Express

    $65 CAD
    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
    Can depart from: Windsor Area, Detroit Area, Sarnia Area, London Area
  • BEST SELLER
    Woman taking a photo from the passenger seat of a car.

    Backroad Bliss

    $65 CAD
    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
    Can depart from: Ottawa Area, Montreal Area
  • GREAT WEEKEND GETAWAY
    Two women on a beach looking out at the water

    Bayside Wonders

    $65 CAD
    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
    Can depart from: Kitchener-Waterloo Area, Toronto Area, Barrie Area
  • 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 CAD
    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
    Can depart from: Kingston Area, Ottawa Area
  • SCENIC ROUTE
    Historic white house underneath a vibrant blue sky.

    Hidden Gems of Huronia

    $65 CAD
    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
    Can depart from: Toronto Area, Barrie Area
  • PERFECT OVERNIGHT GETAWAY
    Lighthouse overlooking the water

    Curiosities & Coastlines

    $65 CAD
    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
    Can depart from: Kitchener-Waterloo Area, Goderich Area, Collingwood Area
  • GREAT SUMMER ROADTRIP
    Hidden Hideaways

    Hidden Hideaways

    $65 CAD
    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.
    Can depart from: Ottawa Area, Montreal Area
  • BEST SELLER
    Maritime boats and boathouses.

    Coastal Crawl

    $65 CAD
    Get out of town and feel the ocean breeze in your hair. This trip perfectly combines iconic Nova Scotia views with small town hidden gems.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Halifax Area
  • NEW SUMMER ROAD TRIP!
    Cheese shop photographed from doorway.

    The Cheese & Charm Trail

    $65 CAD
    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
    Can depart from: London Area, Brantford-Area, Kitchener-Waterloo Area, Hamilton Area, Sarnia Area
  • HIDDEN GEMS
    Workers filling up a glasses of beer at a brewery

    Gardens, Trails & Local Ales

    $65 CAD
    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
    Can depart from: Ottawa Area
  • Digital Download Only
    Aerial view of Toronto cityscape during sunset, showcasing various buildings and the CN Tower.

    Toronto Gems

    $39.00 CAD
    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!
    Can depart from: Toronto Area, Kitchener-Waterloo Area, London Area
  • best done spring-fall
    Quintessential Québec

    Quintessential Québec

    $65 CAD
    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
    Can depart from: Kingston Area, Ottawa Area, Montreal Area
  • GREAT SUMMER ROAD TRIP
    Two people sitting on a rock overlooking a scenic view of mountains during sunset.

    Valley Views

    $65 CAD
    Down in the valley where the green grass grows...you'll find charming towns, get lost in lush vineyards, take in vast views and hike scenic trails on this countryside road trip.
    • Dog-Friendly
    • Kid-Friendly
    Can depart from: Halifax Area
  • 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
Three women walking through tulip fields
Winding roads through mountains at sunrise

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