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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  • BEST SELLER
    Hudson River Hideaways

    Hudson River Hideaways

    $65 CAD
    An iconic road trip route with a twist! We've found countless hidden hideaways along the Hudson including; crumbling ruins, quaint towns, spooky cemeteries and more.
    • Dog-Friendly
  • 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 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
  • 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
  • CAN BE DONE YEAR-ROUND
    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
  • Returns Sept. 9!
    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
    Sale
  • BEST SELLER
    Sandhills Sauntering

    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
    Sale
  • Road Map

    Road Map

    Regular price $6.00 CAD
    Everyone misses a good ol' traditional road map. This is an essential item for any road trip (and it looks great in photos).
  • NEW ENGLAND CHARM
    Vintage Vibes & Views

    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
  • BEST SELLER
    Scenic Sights & Tasty Bites

    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
  • GREAT SUMMER ROADTRIP
    Waterside Bliss

    Waterside Bliss

    $65 CAD
    Boardwalks, beaches and bites make this charming itinerary the ultimate road trip!
    • 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
  • 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
  • GREAT SUMMER ROADTRIP
    Peculiar Wonders

    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
  • FOR THE PARANORMAL EXPLORER
    Black and white photo of an old house.

    An Unusual Adventure

    $65 CAD
    If you're the paranormal podcast listener in your friend group, this trip is for you! This area is filled with all things unusual, spooky, and abandoned. You'll also learn about some local legends, ghost stories and folklore throughout your day.
    • Dog-Friendly
  • GREAT SUMMER ROADTRIP
    Valley Views

    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
  • BEST SELLER
    Bowen Island Gems

    Bowen Island Gems

    $65 CAD
    This is a local's guide to hidden gems and favourite stops on Bowen Island. With secret beaches, surprise hikes and funky shops...there's something for everyone on this trip.
    • Kid-Friendly
  • An iconic route
    Secrets on the Scenic Route

    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
  • A PERFECT COUNTRYSIDE DRIVE
    Red covered bridge over water.

    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
  • A LITTLE BIT OF EVERYTHING
    Treats & Trails

    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!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • BEST SELLER
    Funky Farms & Storybook Tales

    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 much more.
    • Accessible
    • Kid-Friendly
  • BEST SELLER
    Old Florida Trail

    Old Florida Trail

    $65 CAD
    Go back in time and visit old Florida. You'll visit delightful small towns, dig into local fare, explore a few outdoor adventures, and fill up your camera roll with quirky photo ops.
    • Kid-Friendly
  • GREAT YEAR-ROUND TRIP
    Quirky Delights

    Quirky Delights

    $65 CAD
    Not too far from home you'll discover a ton of quirky destinations. Think outdoor folk art, funky eats in a small town, hidden gem riverside strolls, and a local alpaca farm.
    • Accessible
    • 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!