Woman holding four Guess Where Trips envelopes while on road trip

Winter Road 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

  • MOTHER'S DAY PICK
    Local Markets & Picturesque Towns

    Local Markets & Picturesque Towns

    $65 CAD
    One of our best-selling trips, and for a good reason. Stops include historic towns, local markets, eateries and hidden gems. This trip makes a great gift because of its versatility.
    • Accessible
    • Kid-Friendly
  • STAFF PICK
    The Small Town Charm Trail

    The Small Town Charm Trail

    $65 CAD
    You know those towns that are described as 'blink-and-you'll-miss-it'? They often have the most amazing hidden gems! Get to know a few small pockets of Ontario with this surprise road trip.
    • Accessible
    • Kid-Friendly
  • MOTHER'S DAY PICK
    Woman sitting on a rocky shore overlooking a river.

    Riverside Roaming

    $65 CAD
    Start your day in a picture-perfect town by the river before strolling along boardwalks, dining at a funky distillery, indulging at farm shops and so much more. This trip is a nice distance from the city and can be done year-round!
    • Kid-Friendly
    • Accessible
  • BEST SELLER
    A group of people toasting with glasses of beer and wine at a social gathering, with blurred faces for privacy.

    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. This itinerary has it all and is not too far from the city.
    • Accessible
    • Kid-Friendly
  • HIDDEN GEMS IN THE NIAGARA REGION!
    The Sweet & Scenic Route

    The Sweet & Scenic Route

    $65 CAD
    A little sweet, a little scenic - this road trip blends cozy cafés, local wines, and maple treats with easy trails, waterfalls, and serene ponds. Perfect for a girls' getaway or a romantic day trip! *Note that this trip can be taken in the summer months; however, the waterfalls may slow to a trickle in the hot weather!
    • Accessible
    • Dog-Friendly
  • BEST SELLER
    Two people walking in a field with a mountain in the background.

    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
  • MOTHER'S DAY PICK
    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 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
  • GREAT YEAR-ROUND TRIP
    A person outdoors holding a camera up to their face, with a body of water and a blurred background.

    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
  • CLOSE TO ORLANDO
    Wooden boardwalk trail in a lush green forest setting

    Boardwalks, Brews & Markets

    $65 CAD
    The name really says it all! Explore marvelous markets with food stalls and local artisans, enjoy a couple brews, and stroll along easy boardwalk trails.
    • Accessible
  • TONS OF TASTY BITES + SHOPS
    A person holding up a sugar-coated doughnut, likely enjoyed as part of the 'A Taste of Amish Country' experience.

    A Taste of Amish Country

    $65 CAD
    Escape to the quiet charm of Amish country for cheese tastings, sweet treats, craft shops, funky museums, and incredible historic photo ops - all set against peaceful countryside scenery.
    • Kid-Friendly
    • Accessible
  • CYCLE FRIENDLY
    Sunset over a river with trees in the foreground

    A Riverside Ramble

    $65 CAD
    Wander through colorful sculptures, charming boutiques, and local eateries before discovering breathtaking riverside gems that are so photo-worthy, your camera roll is sure to fill up!
    • Accessible
    • Kid-Friendly
  • GREAT WEEKEND GETAWAY
    Man standing on a road looking up among towering trees

    Forests & Funky Finds

    $65 CAD
    This trip is the perfect overnight getaway! As you're driving through the woods, you'll hop between the cutest small towns full of charming shops and eateries.
    • Kid-Friendly
    • Dog-Friendly
  • GREAT YEAR-ROUND TRIP
    A scenic view of mountains and a clear sky with clouds, framed by trees in the foreground.

    Mountain Marvels

    $65 CAD
    This family-friendly trip is the ultimate way to escape the city and head to the mountains. Stroll the streets of charming small towns, explore quirky art and museums, indulge in tasty bites & brews and enjoy the surprise!
    • Accessible
    • Kid-Friendly
  • STAFF PICK
    Elegant Estates & Outdoor Art

    Elegant Estates & Outdoor Art

    $65 CAD
    Just a short drive from Indy, you'll find a world full of elegant estates, whimsical gardens, and colorful outdoor art. We'll tell you all of the quirky fun facts and historic moments that make these spots so unique!
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
  • PERFECT FOR MOVIE BUFFS
    A person holding a camera and taking a photo, with a focus on the camera and the person's hand

    Cinema & Scenery

    $65 CAD
    Discover hidden art, channel your inner movie star, indulge in tasty bites, and enjoy a waterside stroll. This captivating adventure offers a perfect blend of creativity, culture, and coastal charm.
    • Kid-Friendly
    • Accessible
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

Take Our Quiz to Find Out

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

Take the Quiz
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!