Woman holding four Guess Where Trips envelopes while on road trip

All Products

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

  • SCENIC ROAD TRIP
    Groves, Gardens & Grapevines

    Groves, Gardens & Grapevines

    $55 CAD Sale
    This incredibly picturesque road trip is full of whimsical gardens, lookout points, wineries, and easy strolls along forest paths. We think it's an area you'll want to come back to time and time again.
    • Kid-Friendly
    Sale
  • CAN BE DONE IN WINTER
    A Riverside Ramble

    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 OVERNIGHT TRIP
    Seaside Legends

    Seaside Legends

    $65 CAD
    Little local legends are sprinkled throughout your day, telling the story of an iconic area of Florida. Expect picturesque beaches, tasty eats, a historic city, and so much more.
    • Kid-Friendly
    • Dog-Friendly
  • GREAT WEEKEND TRIP
    Wacky Wonders

    Wacky Wonders

    $65 CAD
    A little funky, a little unexpected, and totally unforgettable—this road trip is a whirlwind of colorful folk art, quirky roadside stops, scenic detours, and bites worth savoring. The only rule? Embrace the unexpected.
  • Great For Active families
    Sweet Sensations

    Sweet Sensations

    $65 CAD
    Between making a furry friend at a farm, enjoying local eateries, walking to quirky ruins in the woods and exploring the sweetest small town, this trip will make all five senses come to life all day!
    • Kid-Friendly
    • Accessible
  • EXPLORE SALEM
    Witchy Wonders

    Witchy Wonders

    $65 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
  • GREAT YEAR-ROUND TRIP
    Mountain Marvels

    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 For Families!
    All Things Charming

    All Things Charming

    $65 CAD
    From serene lakeside views and quaint small town charm to playful animal encounters and a whimsical museum, this captivating road trip promises to create unforgettable memories for everyone in your group
    • Kid-Friendly
  • GREAT YEAR-ROUND TRIP
    Outback Oasis

    Outback Oasis

    $65 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
  • A CLOSE TO HOME ADVENTURE
    Timeless Towns & Scenic Sips

    Timeless Towns & Scenic Sips

    $55 CAD Sale
    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
  • BEST SELLER
    Grassy hills leading down to water.

    Coastal Jaunt

    $65 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
  • CYCLE FRIENDLY
    Ojai Oasis

    Ojai Oasis

    $65 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
  • CLOSE TO ATLANTA
    Film & Food Crawl

    Film & Food Crawl

    $65 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
  • FOR THE FOODIES
    Woman running along oceanside.

    Birds, Breezes & Cheeses

    $65 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
  • COASTAL ROAD TRIP
    Sun-Kissed Surprises

    Sun-Kissed Surprises

    CAD
    Get ready to feel the ocean breeze in your hair! We've recommended multiple beaches and the cutest colorful towns full of local shops, walks and eateries.
    • Accessible
    • Kid-Friendly
    Sold out
  • BEST DONE MAY-OCTOBER
    Rivers & Rural Roads

    Rivers & Rural Roads

    $65 CAD
    Riverside roaming strolls, historic highlights, scenic spots for sipping wine or beer, and some of the prettiest rural roads are just a few of the hidden gems you’ll discover on this trip!
    • 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
  • FOR A CLOSE-BY WHIMSICAL ADVENTURE
    Storybook Strolls

    Storybook Strolls

    $65 CAD
    A day full of whimsy, wonder and quirky destinations that will make you feel like you're living in a storybook world. This trip is perfect for the whole road trip crew, from families with kids to girlfriend getaways!
    • Kid-Friendly
  • GREAT YEAR-ROUND TRIP
    Woman looking up through binoculars.

    Adventure in the Glades

    $65 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
  • GREAT WEEKEND GETAWAY
    Forests & Funky Finds

    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
  • Dog-Friendly Trip!
    Falls, Forests & Fables

    Falls, Forests & Fables

    $65 CAD
    Get ready for a day filled with charm and easy outdoor adventures. Start in a small town bursting with colorful murals, then enjoy riverside lookouts and even some surprising wildlife. This trip is perfect for those who love to stay active while exploring!
    • Dog-Friendly
    • Kid-Friendly
  • SPOOKY STORIES
    Eerie Escapes

    Eerie Escapes

    $55 CAD Sale
    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
    Sale
  • CLOSE TO LA
    South Bay Secrets

    South Bay Secrets

    $55 CAD Sale
    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
    Sale
  • SCENIC ROUTE
    Bridges & Beauty

    Bridges & Beauty

    $65 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
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!