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

  • 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
  • GREAT OVERNIGHT GETAWAY
    Grassy landscape with hills.

    Country Treasures

    $65 CAD
    Escape to the country and visit tons of charming bakeries, get your steps in on easy trails, sip something tasty, and end the day in the most amazing small town.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • GREAT FOR FAMILIES
    Quirky & Colorful

    Quirky & Colorful

    $65 CAD
    From charming coffee spots and hidden gardens to quirky museums and haunted tales, this adventure has something unexpected at every turn. Top it all off with shopping, murals, and more in one of Texas’ most vibrant small towns!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • SPOOKY STORIES
    Eerie Escapes

    Eerie Escapes

    $65 CAD
    Step into a day where every stop sends a shiver down your spine. Ghostly whispers in cemeteries, abandoned ruins, and wooded trails full of chilling stories will leave you wondering if any spirits followed you home.
    • Dog-Friendly
    • Accessible
  • A LEISURELY ROAD TRIP
    Woman hiking in a forest

    Woodland Walks & Wineries

    $65 CAD
    Funky forest finds are on every stop, which are perfect for the outdoor adventurer. Unique wineries, bakeries, and a museum celebrating a man we have a lot to thank for are sprinkled in for the more leisurely road tripper.
    • Kid-Friendly
  • FOR COUNTRYSIDE DRIVES
    Cozy Country Charm

    Cozy Country Charm

    $65 CAD
    The perfect blend of rustic allure, cute small towns, cozy cafes, and farmstead feelings makes this a fantastic road trip for those looking to slow down and appreciate the little moments.
    • Kid-Friendly
    • Accessible
  • EXPLORE AN ICONIC AREA
    A red covered bridge crossing a rocky stream, surrounded by green forest.

    Countless Covered Bridges

    $65 CAD
    Take a leisurely drive through the idyllic countryside, hopping from one quaint covered bridge to another. We've sprinkled in a few local eateries and easy trails to give your camera a break! 
    • Dog-Friendly
    • Kid-Friendly
  • FAMILY FRIENDLY
    Colorful houses along a beach.

    Colors & Wonders

    $65 CAD
    This trip is full of colorful wonders - like a short hike to get your heart rate up before you relax with an afternoon beverage, support a local shop, or sip coffee & indulge in delicious baked goods.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • FOR PARANORMAL BUFFS
    Strange & Spooky Sights

    Strange & Spooky Sights

    $65 CAD
    Get ready for a spine-tingling adventure as you explore some of the most haunted and historic spots in the state. Along the way, you'll encounter restaurants and cafes with ghostly legends, strange stories, peculiar museums and haunted objects galore — perfect for anyone who loves a good thrill mixed with quirky charm!
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • Scenic drives!
    Wooden bridge overtop of moving river and surrounded by forest trees.

    Valleys, Vistas & Falls

    $65 CAD
    Wander through lush forests, meet rooftop goats, enjoy a riverside pint, and chase waterfalls on this Vancouver Island road trip packed with quirky charm and breathtaking West Coast views!
    • Kid-Friendly
    • Accessible
    Sale
  • FOR THE PHOTOGRAPHER
    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
  • Great for foodies!
    Cowboy Country Crawl

    Cowboy Country Crawl

    $65 CAD
    Saddle up for a Wild West adventure packed with charm. Snap a few cowboy-inspired photos, savor local flavors, and cool off at a hidden swimming hole. It’s everything you need for an unforgettable day in cowboy country!
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • Perfect summer trip!
    Blue skies overlooking a Vancouver Island pier with a blue building in the distance.

    Seaside Sips & Strolls

    $65 CAD
    Think waterside strolls, blooming gardens, farm-fresh bites, cozy tasting spots, and storybook towns. This surprise-filled Vancouver Island adventure is packed with charm, quirky detours, and nature escapes you’ll be dreaming about later!
    • Kid-Friendly
    • Accessible
  • 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
  • AN ICONIC ROUTE
    Hill Country Harvest

    Hill Country Harvest

    $65 CAD
    Embark on a day of scenic sips and charming discoveries! With visits to stunning wineries, a renowned distillery, a beautiful wildflower farm, and photogenic roadside stops, this is the perfect getaway to explore the best of Hill Country's iconic Highway 290.
    • Accessible
    • Kid-Friendly
  • OUTDOOR ADVENTURES!
    River overlook with trees beginning to change color in the fall.

    Walk on the Wild Side

    $65 CAD
    From Scandinavian treats to rocky riverside hikes and a stop at a wildlife park, this photo-worthy adventure is packed with fresh air, big views, and even a tipple or two at a local winery.
    • Dog-Friendly
    • Kid-Friendly
  • IDEAL SUMMER TRIP!
    Art Trails & River Tales

    Art Trails & River Tales

    $65 CAD
    With riverside bluffs, artistic oddities, and charming small towns, this photo-friendly adventure through southeastern Minnesota is packed with stories waiting to be discovered.
    • Kid-Friendly
    • Dog-Friendly
  • PERFECT FAMILY ROAD TRIP!
    Bison in the middle of a grassy field and grey skies.

    Creatures & Quirks

    $65 CAD
    From towering sculptures and wild bison to waterfalls, eye-spy photo ops, and pints with peacocks, this adventure is as weird and wonderful as they come!
    • Kid-Friendly
    • Accessible
  • CLOSE TO THE CITY!
    Gazebo overlooking a lake on a sunny day.

    Lakeside Treasures

    $65 CAD
    This laid-back road trip blends small-town charm with offbeat surprises and scenic sips. Discover lakeside towns, quirky art gardens, a few furry friends, and the perfect patio pint.
    • 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!