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

  • HIDDEN GEMS
    Gardens, Trails & Local Ales

    Gardens, Trails & Local Ales

    $65 CAD
    If you're into hidden gem breweries and easy outdoor adventures then this is the trip for you! We've also sprinkled in a few bakeries to satisfy your sweet tooth, quirky shops and some local history throughout the day.
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • Best done Spring - Fall
    Waterside Bliss

    Waterside Bliss

    $65 CAD
    Boardwalks, beaches and bites make this charming itinerary the ultimate road trip!
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLER
    Scenic Sights & Tasty Bites

    Scenic Sights & Tasty Bites

    $65 CAD
    Bakeries, breweries & views - oh my! With the perfect mix of outdoor adventures, local farms, and tasty bites, this is the perfect trip for your whole road trip crew. This is the perfect road trip for any Little Women movie fans.
    • Accessible
    • Kid-Friendly
  • BEST DONE JUNE-SEPTEMBER
    Rural Adventures

    Rural Adventures

    $65 CAD
    Scenic driving routes, a ton of photo-worthy views and rural, small town vibes await you on this surprise road trip.
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
  • BEST SELLER
    Offbeat Oddities

    Offbeat Oddities

    $65 CAD
    The quirkiest road trip in central Florida! Historic homes with peculiar stories, off-the- beaten-path eateries, and funky trails & ruins will keep you on your toes throughout the day.
    • Kid-Friendly
  • FOR THE PARANORMAL EXPLORER
    Black and white photo of an old house.

    An Unusual Adventure

    $65 CAD
    If you're the paranormal podcast listener in your friend group, this trip is for you! This area is filled with all things unusual, spooky, and abandoned. You'll also learn about some local legends, ghost stories and folklore throughout your day.
    • Dog-Friendly
  • Best done Spring - Fall
    Peculiar Wonders

    Peculiar Wonders

    $65 CAD
    Unique short hikes, peculiar museums, tasty treats & brews, tons of opportunities for the budding photographer and so much more. Hit the road and discover your new favourite day-trip destination!
    • Dog-Friendly
    • Kid-Friendly
  • NEW ENGLAND CHARM
    Vintage Vibes & Views

    Vintage Vibes & Views

    $65 CAD
    Immerse yourself in quintessential New England charm as you wind along picturesque roads to a number of nature trails, cozy cafes, historic small towns and an incredibly funky garden.
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLER
    Old Florida Trail

    Old Florida Trail

    $65 CAD
    Go back in time and visit old Florida. You'll visit delightful small towns, dig into local fare and have a few outdoor adventures.
    • Kid-Friendly
  • Great Year-Round Trip
    Mysterious Gems

    Mysterious Gems

    $65 CAD
    Truly extraordinary destinations with strange stories and history. Cemeteries abandoned ruins, historic homes and so much more await on this mysterious road trip!
    • Dog-Friendly
  • GREAT YEAR-ROUND TRIP
    Vibrant Vistas & Picturesque Towns

    Vibrant Vistas & Picturesque Towns

    $65 CAD
    Hit the road and explore easy outdoor adventures, outstanding views and small towns that inspired Stars Hollow in Gilmore Girls.
    • Dog-Friendly
  • An iconic route
    Secrets on the Scenic Route

    Secrets on the Scenic Route

    $65 CAD
    This trip combines iconic attractions and quite a few hidden gems before ending in one of the coolest villages in Canada. Can you guess where? Perfect for those wanting to explore this famous route in more detail.
    • Dog-Friendly
  • Best done spring-fall
    Valley Views

    Valley Views

    $65 CAD
    Down in the valley where the green grass grows...you'll find charming towns, get lost in lush vineyards, take in vast views and hike scenic trails on this countryside road trip.
    • Dog-Friendly
    • Kid-Friendly
  • A PERFECT COUNTRYSIDE DRIVE
    Red covered bridge over water.

    Covered Bridges & Baked Goods

    $65 CAD
    This trip is like taking a step back in time! Wind your way through the peaceful countryside to a number of quaint covered bridges and locally owned bakeries, farmers markets, and shops.
    • Kid-Friendly
    • Accessible
  • GREAT YEAR-ROUND TRIP
    Quirky Delights

    Quirky Delights

    $65 CAD
    Not too far from home you'll discover a ton of quirky destinations. Think outdoor folk art, funky eats in a small town, hidden gem riverside strolls, and a local alpaca farm.
    • Accessible
    • Kid-Friendly
  • BEST SELLER
    Island Gems

    Island Gems

    $65 CAD
    This is a local's guide to hidden gems and favourite stops on Bowen Island. With secret beaches, surprise hikes and funky shops...there's something for everyone on this trip.
    • Kid-Friendly
  • HIDDEN GEMS IN THE NIAGARA REGION
    Maple Syrup Farm in Winter

    The Sweet & Scenic Route

    $65 CAD
    A little sweet, a little scenic—this road trip blends cozy cafés, local wines, and maple treats with easy trails, waterfalls, and serene ponds. Perfect for a girls' getaway or a romantic day trip!
    • Accessible
    • Dog-Friendly
  • BEST SELLER
    Woman in winter looking up at snow flakes

    Funky Farms & Storybook Tales

    $65 CAD
    It's no wonder authors flocked to this area of Massachusetts for inspiration! Head out on a picturesque drive and discover farms, boardwalk trails, lots of quirky history and much more.
    • Accessible
    • Kid-Friendly
  • GREAT YEAR-ROUND TRIP
    Secrets of Gettysburg

    Secrets of Gettysburg

    $65 CAD
    Explore Gettysburg and its surrounding area in a whole new way. We’ve made this classic, All-American, bucket list destination easy and fun to do - whether it's your first or fiftieth time! Discover hidden gems and surprising stops while learning more about the turning point of the Civil War.
    • Kid-Friendly
    • Dog-Friendly
  • A LITTLE BIT OF EVERYTHING
    Treats & Trails

    Treats & Trails

    $65 CAD
    Is there anything better than a leisurely day sipping coffee, enjoying tasty treats and meandering along easy boardwalk trails? We think not!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • CLOSE TO ORLANDO
    Boardwalks, Brews & Markets

    Boardwalks, Brews & Markets

    $65 CAD
    The name really says it all! Explore marvelous markets with food stalls and local artisans, enjoy a couple brews, and stroll along easy boardwalk trails.
    • Accessible
  • BEST SELLER
    Two girls sitting in back of crossover SUV.

    A Little Bit of Everything

    $65 CAD
    The perfect distance from Charlotte! From little local shops to an old rail trail and everything in between, this trip truly has something for everyone.
    • Accessible
    • Kid-Friendly
  • SOMETHING FOR EVERYONE
    Cascades & Colors

    Cascades & Colors

    $65 CAD
    Funky colorful towns full of local eateries and shops, a few waterfalls that will leave you in awe and one of the most unusual gardens we have ever seen. You’ll want to get your camera out for this trip!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • BEST SELLER
    The Southwest Quest

    The Southwest Quest

    $65 CAD
    Plenty of sun, strolls and citrus make this the ultimate Southwest Florida road trip. From unique eateries and boardwalk trails to an eerie ghost town and a sunset beach stop, there is truly something for everyone!
    • 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.

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!