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

  • COZY WINTER ROAD TRIP!
    West Coast Wonders

    West Coast Wonders

    $65 CAD
    From castles and waterfalls to windswept seaside walks and quirky local shops, this adventure captures the wild beauty of Vancouver Island’s southwest coast.
    • Dog-Friendly
    • Kid-Friendly
  • CAN BE DONE IN WINTER
    Timeless Towns & Scenic Sips

    Timeless Towns & Scenic Sips

    $49 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
  • CAN BE DONE IN WINTER
    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
  • Last chance!
    A person standing in front of a colorful graffiti-covered wall.

    The Road to Asheville

    $50 CAD Sale
    Grab a sweet treat in a converted church, sip a beer beside a babbling creek, get your steps in on a couple local trails and so much more. This iconic North Carolina destination is the perfect weekend away, so we highly recommend booking a hotel!
    • Dog-Friendly
    • Kid-Friendly
    • Accessible
  • OUTDOOR WINTER ADVENTURES!
    Falls, Forests & Fables

    Falls, Forests & Fables

    Regular price $39.00 CAD
    Sale
    Get ready for a day filled with charm and easy winter adventures. Start in a small town bursting with colorful murals, then take in riverside lookouts, snowy trails, and even some surprising wildlife. This trip is perfect for those who love to stay active while exploring!
    • Dog-Friendly
    • Kid-Friendly
  • CAN BE DONE IN WINTER
    A person taking a photo with a smartphone from a car, capturing a scenic view.

    Picture Perfect Discoveries

    $65 CAD
    Ready for a little mountain meandering? Picturesque historic spots, unique destinations to grab a bite to eat, and a couple charming towns are on your to-do list.
    • Kid-Friendly
    • Dog-Friendly
  • GREAT WEEKEND GETAWAY
    Man standing on a road looking up among towering trees

    Forests & Funky Finds

    $50 CAD Sale
    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
  • HALLMARK MOVIE VIBES!
    All Things Charming

    All Things Charming

    $65 CAD
    From snow-dusted lakeside views and quaint small-town charm to playful animal encounters and a whimsical museum, this captivating road trip promises unforgettable moments for everyone in your group.
    • Kid-Friendly
  • BEST DONE SPRING-FALL
    A sandy trail leading to the water

    Lakeshore Views & Brews

    $65 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
  • CAN BE DONE IN WINTER
    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
  • Last chance!
    Medieval castle-like stone structure with a clear blue sky in the background.

    Storybook Strolls

    $50 CAD Sale
    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
  • BEST SELLER
    Pretty Little Finds

    Pretty Little Finds

    $65 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 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
  • Last chance!
    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
  • Last chance!
    View from inside a wooden covered bridge looking out at a tree-lined road leading to a bright sky.

    Bridges & Beauty

    $50 CAD Sale
    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
  • Last chance!
    A thematic setup featuring items related to witchcraft and Halloween, including pumpkins, candles, books, and various decorative elements on a table.

    Witchy Wonders

    $50 CAD Sale
    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
  • last chance!
    Rivers & Rural Roads

    Rivers & Rural Roads

    $50 CAD Sale
    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
  • CAN BE DONE IN WINTER
    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
  • 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

    Regular price $39.00 CAD
    Sale
    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
  • 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
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!