All Products

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 | best done spring-fall
    Woman looking out of car window.

    All the Pretty Things

    $65 CAD
    Take in all the pretty views and things on this picturesque trip. The itinerary is packed with stunning viewpoints, historic attractions and delicious restaurants and wineries.
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
  • Best done spring-fall
    Sister and brother hugging on a boardwalk.

    Bridges to Beaches

    $65 CAD
    Picturesque bridges to sandy beaches and everything in between. This trip takes you off the beaten path to some of our favourite places in Ontario.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • Best-selling gift | can be done year-round
    Woman taking a selfie, showing the woman behind her taking the photo.

    Brews, Bites, and Everything Nice

    $65 CAD
    This trip is very true to its name, the coolest brews, the tastiest bites and everything else is very nice.
    • Accessible
    • Kid-Friendly
  • Recently relaunched!
    Taste of the Country

    Taste of the Country

    $65 CAD
    This trip is just a short jaunt from Toronto and is perfect for foodies and families! You'll explore incredible farmers markets, cute small towns, a few local spots to grab a drink and an easy wooded trial.
    • Accessible
    • Kid-Friendly
  • Great Fall Trip!
    Spooky black and white photo of a road on a foggy day.

    Beautifully Haunted

    $65 CAD
    Beautifully eerie and oh so haunted! This outdoorsy road trip is full of spooky spots set along a picturesque driving route. A few local eateries and trails are sprinkled throughout the day to keep your energy up while ghost hunting.
    • Dog-Friendly
    • Kid-Friendly
  • Lots of outdoor attractions | Great gift
    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
  • Best done spring-fall
    Southern Express

    Southern Express

    $65 CAD
    This trip takes you to some iconic stops and hidden gems in southern Ontario. It's the perfect combination of outdoor activities, funky restaurants, beaches and historic attractions.
    • Kid-Friendly
    • Dog-Friendly
  • Great for kids! | Can be done year-round
    The Fairy Tale Trail

    The Fairy Tale Trail

    $65 CAD
    This 'mini' trip is designed for families with children under 12. The variety of stroller-friendly and toddler-friendly activities make it a no-fuss day for everyone in the car. We've even included scavenger-style activities throughout the itinerary to keep your kids engaged.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • optional scavenger hunt included
    Toronto Gems

    Toronto Gems

    $65 CAD
    Explore all of the downtown gems in a completely new way. Ditch the car, and walk or bike while you explore what Toronto has to offer. This trip is best for Toronto tourists, those new to the Toronto area, and those who are not super familiar with the Toronto core. The trip has an optional “scavenger hunt" so there is something for you to find and decode at each stop.
  • Best-selling gift | Best done Spring-Fall
    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
  • Available year-round! | Great gift
    Tiny Town Tour

    Tiny Town Tour

    $65 CAD
    Meander along scenic roads while stumbling upon charming tiny towns! This trip has endless photo opportunities, easy outdoor adventures, and plenty of fantastic spots to shop, drink and eat.
    • Dog-Friendly
  • Can be done year-round | Fan Favorite
    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
  • Great year-round trip!
    Riverside Roaming

    Riverside Roaming

    CAD
    This trip will return in 2024.
    • Kid-Friendly
    Sold out
  • Flatlay of Guess Where Trips tote bag, gift card, brochure, keychain and gift wrapping.

    Add On: Gift Box + Tote

    Regular price $22.00 Sale price $16.00 CAD
    Sale
    The perfect addition if you're gifting a road trip to someone special! Let us carefully wrap up your mailed trip in our signature gift box.
    Sale
  • Great Weekend Away Trip!
    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
  • Great for kids! | Can be done year-round
    The Whimsical Route

    The Whimsical Route

    $65 CAD
    This 'mini' trip is designed for families with children over the age of 5. This trip will take you on a number of easy outdoor adventures that provide a variety of kid-friendly options at each stop. We've even included scavenger-style activities throughout the itinerary to keep your kids engaged.
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • Road Trip Game Pack

    Road Trip Game Pack

    Regular price $12.00 Sale price $6.00 CAD
    Sale
    Keep the young ones busy with a fun game pack to play with on the road! Dozens of games and activities to keep kids of all ages entertained.
    Sale
  • best done spring-fall
    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.
  • Great Year-Round Trip
    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
  • Best done spring-fall
    The Butter Tart Trail

    The Butter Tart Trail

    CAD
    This trip is no longer available.
    • Accessible
    • Kid-Friendly
    Sold out
  • Best done spring-fall
    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
    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
  • 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
  • Available 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

CAN'T DECIDE?

Take Our Quiz to Find Out

Select your region and interests to find the best trip for you.

Take the Quiz

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!