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

  • EXPLORE MIAMI
    Mysteries of Miami

    Mysteries of Miami

    Regular price $65.00 Sale price $50.00 CAD
    If you're into true crime and mysteries then this is the trip for you! From murder mysteries and spooky cemeteries to ghosts and the supernatural, this Miami road trip is truly full of unusual destinations.
    • Accessible
    Sold out
  • PERFECT FOR MOVIE BUFFS
    Cinema & Scenery

    Cinema & Scenery

    $39 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
  • THE ULTIMATE WEEKEND AWAY
    Solvang Splendors

    Solvang Splendors

    $39 CAD
    Escape to the Santa Ynez Valley and explore cute small towns, the roaming vineyard hills, local farms and so much more. We highly recommend turning this trip into a weekend adventure! 
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
  • FOR PARANORMAL BUFFS
    Strange & Spooky Sights

    Strange & Spooky Sights

    $39 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
  • Great for foodies!
    Cowboy Country Crawl

    Cowboy Country Crawl

    $39 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 FAMILY ROAD TRIP!
    Bison in the middle of a grassy field and grey skies.

    Creatures & Quirks

    $39 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
  • AN ICONIC ROUTE
    Hill Country Harvest

    Hill Country Harvest

    $39 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
  • LAST CHANCE
    The Explorer's Route

    The Explorer's Route

    CAD
    Take a step back in time with this family-friendly adventure! With so many quaint towns, easy outdoor adventures, photo-ops and local eateries, you'll have so much to explore.
    • Dog-Friendly
    • Accessible
    Sold out
  • CLOSE TO THE CITY!
    Gazebo overlooking a lake on a sunny day.

    Lakeside Treasures

    $39 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
  • 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
  • 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
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.

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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!