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 FALL TRIP
    A Riverside Ramble

    A Riverside Ramble

    $39 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
  • SOMETHING FOR EVERYONE
    Park bench and fountain at the end of a brick path in a garden.

    Antique Adventures

    $39 CAD
    This leisurely trip packs a punch! Expect a variety of antique shops (both small and large), cozy cafes, funky eateries, effortless outdoor escapades and haunted stops along the way. The best part? It's only a quick jaunt from the city.
    • Accessible
  • A CLOSE TO HOME ADVENTURE
    Timeless Towns & Scenic Sips

    Timeless Towns & Scenic Sips

    $39 CAD
    Brews, bites and a whole lot of history! From small town charm to tasty tipples and one of the most unique (and eerie) trails we've ever found, this road trip has something for everyone.
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • OFF-THE-BEATEN-PATH ROAD TRIP
    Woman taking photo can be seen in side view mirror of car.

    All Things Strange & Beautiful

    $39 CAD
    A few famous filming spots, scenic drives, local eateries and an eerie abandoned area are just some of the strange and beautiful things you'll discover on this road trip.
    • Accessible
    • Kid-Friendly
  • BEST SELLER
    Grassy hills leading down to water.

    Coastal Jaunt

    $39 CAD
    Just across the Golden Gate Bridge, escape the city for a day by the coast. Beach breaks, epic overlooks, walks along the water and local eateries to fuel up at make this the perfect trip close to home.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • EXPLORE SALEM
    Witchy Wonders

    Witchy Wonders

    $39 CAD
    This road trip will have you exploring the Salem witch trials, haunted history and a few iconic Hocus Pocus locations. This trip can be done throughout the year. If you're travelling during the month of October some attractions need to be pre-booked as the area gets significantly busier.
    • Accessible
    • Kid-Friendly
  • FOR THE FOODIES
    Woman running along oceanside.

    Birds, Breezes & Cheeses

    $39 CAD
    Say cheese! That's right, we've rounded up the best cheese shops and the most photo-worthy moments a road trip can have. You'll feel the breeze in your hair as you walk down coastal trails and quaint streets.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • GREAT FALL TRIP
    Mountain Marvels

    Mountain Marvels

    $39 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
  • SPOOKY STORIES
    Eerie Escapes

    Eerie Escapes

    $39 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
  • CYCLE FRIENDLY
    Ojai Oasis

    Ojai Oasis

    $39 CAD
    Small-town charm is at the center of this Ojai road trip. Shop 'till you drop, indulge in local wine and sweet treats, and meander along a few short trails. This trip is cycle-friendly too!
    • Accessible
    • Dog-Friendly
  • SCENIC ROUTE
    Bridges & Beauty

    Bridges & Beauty

    $39 CAD
    Get ready to wind your way through scenic tree-lined roads, cross charming covered bridges, sip at cozy wineries, hike stunning trails, and maybe even get a chill from a ghostly tale or two.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • BEST DONE SPRING-FALL
    Lakeshore Views & Brews

    Lakeshore Views & Brews

    $39 CAD
    Stroll along a breathtaking boardwalk, dip your does in the cool water, sip craft drinks in unique destinations, and take lots of funky photos! This road trip will certainly let you unwind from the hustle and bustle of the city.
    • Kid-Friendly
    • Accessible
  • LAST CHANCE
    Film & Food Crawl

    Film & Food Crawl

    CAD
    Georgia is often called the "Hollywood of the South" so we've rounded up a few of our favorite filming spots. Local cafes, breweries, eateries and farmers markets are also sprinkled in to keep your energy up!
    • Accessible
    Sold out
  • 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
  • GREAT OVERNIGHT GETAWAY
    Grassy landscape with hills.

    Country Treasures

    $39 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
  • STAFF PICK
    Cozy Country Charm

    Cozy Country Charm

    $39 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
  • BEST SELLER
    South Bay Secrets

    South Bay Secrets

    $39 CAD
    Coastal walks and lighthouse views make this South Bay road trip incredibly picturesque. It's the perfect choice for a trip close to home!
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • FAMILY FRIENDLY
    Colorful houses along a beach.

    Colors & Wonders

    $39 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
  • LAST CHANCE
    Woman looking up through binoculars.

    Adventure in the Glades

    CAD
    Scenic views, unique boardwalks and funky roadside attractions can all be found when you escape to the Everglades. Just make sure you keep your eyes peeled for those pesky gators!
    • Accessible
    Sold out
  • Perfect Weekend Getaway!
    Pretty Little Finds

    Pretty Little Finds

    $39 CAD
    With plenty of picture-perfect moments, quirky stops, and a bit of everything from bees to barns, this adventure promises the perfect blend of beauty and cozy vibes. Think funky florals, farm-fresh finds and plenty of antiques!
    • Kid-Friendly
    • Accessible
  • GREAT FOR FAMILIES
    Quirky & Colorful

    Quirky & Colorful

    $39 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
  • EPIC VIEWS
    Ocean photographed from atop a hill.

    Down by the Bay

    $39 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
  • FOR THE PHOTOGRAPHER
    Elegant Estates & Outdoor Art

    Elegant Estates & Outdoor Art

    $39 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 WEEKEND GETAWAY
    Sonoma Sips & Strolls

    Sonoma Sips & Strolls

    $39 CAD
    Scenic sipping and picturesque strolls can be found in this iconic area of California! We've found hidden gem wineries, tasty food shops, a few easy trails and so much more.
    • Dog-Friendly
    • Accessible
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

Take Our Quiz to Find Out

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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!