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

  • CAN BE DONE IN WINTER
    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
  • PENNSYLVANIA & NEW JERSEY
    Festive Farms & Holiday Charm

    Festive Farms & Holiday Charm

    Regular price $65.00 Sale price $39.00 CAD
    Celebrate the season with farm-fresh bites, twinkly markets, and festive small-town charm. From history-rich stops to holiday treats and cozy sips, this merry adventure will soon become your new favorite winter tradition.
    • Accessible
    • Kid-Friendly
    Sale
  • COZY TRIP NEAR THE CITY!
    Elegant Estates & Outdoor Art

    Elegant Estates & Outdoor Art

    $65 CAD
    Just a short drive from Indy, you’ll find a world of elegant estates, whimsical gardens, and colorful outdoor art - all looking a little extra magical when dusted with snow. We’ll share the quirky fun facts and historic moments that make these spots so unique!
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
  • CAN BE DONE IN WINTER
    Ocean photographed from atop a hill.

    Down by the Bay

    $65 CAD
    You don't have to go far from home to have an epic adventure! The scenic viewpoints and easy trails are endless on this trip. And while you won't see watermelons grow, there are tons of fantastic local eateries along the way.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • LAST CHANCE
    Outback Oasis

    Outback Oasis

    CAD
    The perfect combination of easy outdoor adventures, browsing through farm markets, and enjoying a slower pace. You'll feel so at ease by the end of your road trip!
    • Accessible
    • Kid-Friendly
    Sold out
  • Scenic drives!
    Wooden bridge overtop of moving river and surrounded by forest trees.

    Valleys, Vistas & Falls

    Regular price $65.00 Sale price $39.00 CAD
    Sale
    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
  • THE ULTIMATE WEEKEND AWAY
    Joshua Tree Journey

    Joshua Tree Journey

    $65 CAD
    Think cowboy towns, desert trails, rooftop cacti, and a whole lot of quirky charm. This road trip blends epic eats, funky photo ops and offbeat art with your journey to Joshua Tree National Park—whether it’s your first time or your fifth.
    • Dog-Friendly
    • Kid-Friendly
  • PERFECT FOR MOVIE BUFFS
    Cinema & Scenery

    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
  • FOR PARANORMAL BUFFS
    Strange & Spooky Sights

    Strange & Spooky Sights

    Regular price $39.00 CAD
    Sale
    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

    $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

    Regular price $65.00 Sale price $39.00 CAD
    Sale
    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
    Sale
  • CAN BE DONE IN WINTER
    Solvang Splendors

    Solvang Splendors

    $65 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
  • 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
  • GREAT YEAR-ROUND!
    Art Trails & River Tales

    Art Trails & River Tales

    $65 CAD
    With snow-dusted riverside bluffs, artistic oddities, and cozy small towns, this photo-friendly adventure through southeastern Minnesota is packed with stories waiting to be discovered.
    • Kid-Friendly
    • Dog-Friendly
  • CAN BE DONE IN WINTER
    Tastes & Trails of Malibu

    Tastes & Trails of Malibu

    $65 CAD
    This iconic route along the PCH is full of hidden gems and epic viewpoints. Put your walking shoes on, save room for awesome eats, and get ready to be beachside!
    • Kid-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
  • ONTARIO
    All Things Merry & Bright

    All Things Merry & Bright

    Regular price $65.00 Sale price $39.00 CAD
    If you're looking for a road trip that is full of festivity and holiday cheer, look no further! Meander down decorated streets with a warm beverage in hand, shop for that hard-to-buy-for person at quaint markets, and find your perfect Christmas tree.
    • Accessible
    • Kid-Friendly
    Sale
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

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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!