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 SELLER
    Quirky Gems

    Quirky Gems

    $65 CAD
    Our best-selling trip from Calgary! 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 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
  • 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
    • Dog-Friendly
  • BEST SELLER
    River running through forest.

    Along the River

    $55 CAD Sale
    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
    Sale
  • 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 SELLER
    Whimsical Wonders

    Whimsical Wonders

    $65 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
  • AN ICONIC ROUTE
    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
  • 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.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • BEST SELLER
    Maritime boats and baothouses.

    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
  • 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
  • BEST SELLER
    Sandhills Sauntering

    Sandhills Sauntering

    $55 CAD Sale
    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
  • PERFECT YEAR-ROUND
    Haunts, Hikes & History

    Haunts, Hikes & History

    $55 CAD Sale
    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
  • 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 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
  • 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 an incredibly funky garden.
    • Kid-Friendly
    • Dog-Friendly
  • GREAT SUMMER ROADTRIP
    Peculiar Wonders

    Peculiar Wonders

    $65 CAD
    Unique short hikes, peculiar museums, tasty treats & brews, tons of opportunities for the budding photographer and so much more. Hit the road and discover your new favourite day-trip destination!
    • 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
  • 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
    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
  • 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 and have a few outdoor adventures.
    • Kid-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
    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

CAN'T DECIDE?

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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!