Woman holding four Guess Where Trips envelopes while on road trip

Our 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

  • Best done spring-fall
    Southern Express

    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
  • best done spring-fall
    Views & Secret Stops

    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
  • 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
  • BEST SELLING GIFT
    Quirky Gems

    Quirky Gems

    $65 CAD
    Our best-selling Calgary road trip! Hit the road and visit some quintessential Alberta towns, eat at funky restaurants, support local businesses, and explore picturesque hikes and natural attractions. All without venturing too far from the city!
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLING GIFT
    River running through forest.

    Along the River

    $39 CAD
    Meander through tiny towns along the river that are brimming with hidden gems. There are countless photo-worthy moments and memories to make on this easygoing scenic road trip.
    • Accessible
    • Kid-Friendly
  • BEST SELLING GIFT
    Whimsical Wonders

    Whimsical Wonders

    $39 CAD
    Escape to hidden gem destinations that make you feel like you've stepped into a fairytale world. Lucious gardens, charming towns and whimsical photo ops make this the perfect road trip.
    • Kid-Friendly
    • Accessible
  • CAN BE DONE IN WINTER
    Rocky Mountain Route

    Rocky Mountain Route

    $65 CAD
    One of the most iconic road trips in the world with a few secret surprises along the way. Incredible mountain towns, tasty local brews and food and a ton of photo-worthy views! Want to keep going towards Jasper? We included a 'want to keep going' section just in case.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLING GIFT
    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
  • THE PERFECT FALL ROAD TRIP
    Butter Tarts, Boos & Brews

    Butter Tarts, Boos & Brews

    $65 CAD
    Equal parts spooky and cozy, this autumn road trip mixes haunted tales with scenic drives, eerie landmarks, farm markets, local brews, and ooey-gooey butter tarts you’ll be dreaming about all season.
    • Kid-Friendly
    • Accessible
  • GREAT FOR A WEEKEND AWAY
    Winding Roads & Historic Gems

    Winding Roads & Historic Gems

    $39 CAD
    Discover photo-worthy hidden gems along winding roads as you make your way to an iconic road trip destination.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • 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
  • ONTARIO
    All Things Merry & Bright

    All Things Merry & Bright

    $65 CAD
    If you're looking for a road trip that is full of festivity and holiday cheer, look no further! Meander down decorated streets with a warm beverage in hand, shop for that hard-to-buy-for person at quaint markets, and find your perfect Christmas tree.
    • Accessible
    • Kid-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
  • CLOSE TO OTTAWA
    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
  • PERFECT YEAR-ROUND
    Haunts, Hikes & History

    Haunts, Hikes & History

    $39 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
  • BEST SELLING GIFT
    Sandhills Sauntering

    Sandhills Sauntering

    $39 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
  • NEW ENGLAND CHARM
    Vintage Vibes & Views

    Vintage Vibes & Views

    $39 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 SELLING GIFT
    Scenic Sights & Tasty Bites

    Scenic Sights & Tasty Bites

    $39 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
  • CAN BE DONE IN WINTER
    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
  • BEST DONE SPRING-FALL
    Waterside Bliss

    Waterside Bliss

    $39 CAD
    Boardwalks, beaches and bites make this charming itinerary the ultimate road trip!
    • Kid-Friendly
    • Dog-Friendly
  • 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
  • BEST DONE SPRING-FALL
    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
  • A LITTLE BIT OF EVERYTHING
    Treats & Trails

    Treats & Trails

    $39 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 SELLING GIFT
    Offbeat Oddities

    Offbeat Oddities

    $39 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
Three women walking through tulip fields
Winding roads through mountains at sunrise

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Gift-a-Trip

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