Woman holding four Guess Where Trips envelopes while on road trip

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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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  • GREAT FOR A WEEKEND AWAY
    Winding Roads & Historic Gems

    Winding Roads & Historic Gems

    $65 CAD
    Discover photo-worthy hidden gems along winding roads as you make your way to an iconic road trip destination filled with history and views.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • FATHER'S DAY PICK
    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
  • Digital Download Only
    Aerial view of Toronto cityscape during sunset, showcasing various buildings and the CN Tower.

    Toronto Gems

    Regular price $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!
  • BEST SELLER
    A group of people enjoying outdoor drinks and food, engaged in conversation in a green, leafy setting.

    The Taste Trail

    $65 CAD
    This road trip will take you to some funky eateries, family farms, wineries, cideries, and a whole lot more. To offset the treats, we've included a few whimsical hikes to end your day.
    • Accessible
  • 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
  • FATHER'S DAY PICK
    Woman standing in front of a waterfall.

    Chasing Waterfalls

    $65 CAD
    Don't let TLC lead you astray. You should definitely go chasing waterfalls! This trip is jam-packed with good food, picturesque waterfalls, and quirky gems.
    • Dog-Friendly
  • NEW ENGLAND CHARM
    A picturesque street in a New England town with a two-story house adorned with an American flag, surrounded by cozy buildings and greenery.

    Vintage Vibes & Views

    $65 CAD
    Immerse yourself in quintessential New England charm as you wind along picturesque roads to a number of nature trails, cozy cafes, historic small towns and picturesque beaches.
    • Kid-Friendly
    • Dog-Friendly
  • GREAT SUMMER ROADTRIP
    Rural Adventures

    Rural Adventures

    $65 CAD
    Scenic driving routes, a ton of photo-worthy views and rural, small town vibes await you on this surprise road trip.
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
  • FATHER'S DAY PICK
    A winding road surrounded by trees with autumn leaves

    Scenic Sights & Tasty Bites

    $65 CAD
    Bakeries, breweries & views - oh my! With the perfect mix of outdoor adventures, local farms, and tasty bites, this is the ideal trip for your whole road trip crew. The perfect road trip for any Little Women movie fans, too!
    • Accessible
    • Kid-Friendly
  • 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
  • PERFECT YEAR-ROUND
    Haunts, Hikes & History

    Haunts, Hikes & History

    $65 CAD
    From haunted happenings to easy strolls and historic hot spots, this trip has a little bit of everything for everyone!
    • Kid-Friendly
    • Dog-Friendly
  • GREAT SUMMER ROADTRIP
    A person wearing a yellow sweater is taking a photograph with a camera, standing against a backdrop of green trees.

    Peculiar Wonders

    $65 CAD
    Travel through time and terrain on this Alberta road trip packed with scenic strolls, quirky museums, epic photo ops, and fun for all ages. From lush gardens and lakeside boardwalks to towering trestle bridges and even free-roaming bison, this one's full of "wait, where are we?" moments—in the best way possible.
    • Kid-Friendly
    • Dog-Friendly
    Sale
  • DIGITAL ONLY
    Woman spinning on the beach.

    Waterside Bliss

    Regular price $39.00 CAD
    Beach breezes, coastal eats, and charming strolls await on this picturesque day trip. You’ll wander waterfront boardwalks, explore historic homes, and discover secret spots only the locals know - all with a side of sandy serenity and small-town charm.
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLER
    Man walking through a forest on a dirt path

    Sandhills Sauntering

    $65 CAD
    Picturesque drives beneath towering trees make this an incredibly scenic trip. Sandhills Sauntering is full of epic places to eat, tons of photo-worthy moments and a hidden gem that will leave you speechless.
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • An winter route
    A scenic view of a road leading towards mountains with green trees on both sides.

    Secrets on the Scenic Route

    $65 CAD
    This trip combines iconic attractions and quite a few hidden gems before ending in one of the coolest villages in Canada. Can you guess where? Perfect for those wanting to explore this famous route in more detail.
    • Dog-Friendly
  • FOR THE PARANORMAL EXPLORER
    Black and white photo of an old house.

    An Unusual Adventure

    $65 CAD
    A spooky Southern New Jersey road trip with abandoned spots, local legends, and eerie stops.
    • Dog-Friendly
  • A LITTLE BIT OF EVERYTHING!
    A box of assorted donuts with different toppings and glazes.

    Treats & Trails

    $65 CAD
    Is there anything better than a leisurely day sipping coffee, enjoying tasty treats and meandering along easy boardwalk trails? We think not, and you'll find all of that and more in this Michigan road trip!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • 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
  • BEST SELLER
    Offbeat Oddities

    Offbeat Oddities

    $65 CAD
    The quirkiest road trip in central Florida! Historic homes with peculiar stories, off-the- beaten-path eateries, and funky trails & ruins will keep you on your toes throughout the day.
    • Kid-Friendly
  • SOMETHING FOR EVERYONE
    A scenic view of a waterfall surrounded by greenery with a bridge in the background.

    Cascades & Colors

    $65 CAD
    Funky, colorful towns full of local eateries and shops, a few waterfalls that will leave you in awe and one of the most unusual gardens we have ever seen. You’ll want to get your camera out for this trip!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • A PERFECT COUNTRYSIDE DRIVE
    Covered Bridges & Baked Goods

    Covered Bridges & Baked Goods

    $65 CAD
    This trip is like taking a step back in time! Wind your way through the peaceful countryside to a number of quaint covered bridges and locally owned bakeries, farmers markets, and shops.
    • Kid-Friendly
    • Accessible
  • GREAT YEAR-ROUND TRIP
    Vibrant Vistas & Picturesque Towns

    Vibrant Vistas & Picturesque Towns

    $65 CAD
    Hit the road and explore easy outdoor adventures, outstanding views and small towns that inspired Stars Hollow in Gilmore Girls.
    • Dog-Friendly
  • Mint Road Trip Journal

    Mint Road Trip Journal

    Regular price $25.00 CAD
    Track all your local adventures - big or small!
  • BEST SELLER
    Red barn with trees behind it.

    Funky Farms & Storybook Tales

    $65 CAD
    It's no wonder authors flocked to this area of Massachusetts for inspiration! Head out on a picturesque drive and discover farms, boardwalk trails, lots of quirky history and so much more.
    • Accessible
    • Kid-Friendly
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

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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!