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

  • Digital Download Only
    Toronto Gems

    Toronto Gems

    Regular price $39.00 USD
    Explore all of Toronto's downtown gems in a completely new way - ditch the car and walk or bike while you explore! This trip is best for anyone who isn't super familiar with the Toronto core, plus there's an optional “scavenger hunt" so there is something for you to find and decode at each stop!
  • BEST SELLER
    The Taste Trail

    The Taste Trail

    $65 USD
    This road trip will take you to some funky eateries, family farms, wineries, cideries, and a whole lot more. To offset the treats, we've included a few whimsical hikes to end your day.
    • Accessible
  • best done spring-fall
    Quintessential Québec

    Quintessential Québec

    $49 USD Sale
    Gorgeous drives, picturesque towns, historic hikes, phenomenal food and so much more. You'll quickly fall in love with the area and want to come back again and again.
    • Dog-Friendly
    • Kid-Friendly
    Sale
  • THE PERFECT FALL ROAD TRIP
    Butter Tarts, Boos & Brews

    Butter Tarts, Boos & Brews

    Regular price $65.00 USD
    Equal parts spooky and cozy, this autumn road trip mixes haunted tales with scenic drives, eerie landmarks, farm markets, local brews, and ooey-gooey butter tarts you’ll be dreaming about all season.
    • Kid-Friendly
    • Accessible
    Sold out
  • BEST DONE SPRING - FALL
    Woman standing in front of a waterfall.

    Chasing Waterfalls

    $65 USD
    Don't let TLC lead you astray. You should definitely go chasing waterfalls! This trip is jam-packed with good food, picturesque waterfalls, and quirky gems.
    • Dog-Friendly
  • NEW ENGLAND CHARM
    Vintage Vibes & Views

    Vintage Vibes & Views

    $65 USD
    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 picturesque beaches.
    • Kid-Friendly
    • Dog-Friendly
  • CAN BE DONE IN WINTER
    Rural Adventures

    Rural Adventures

    $65 USD
    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
    Scenic Sights & Tasty Bites

    Scenic Sights & Tasty Bites

    $65 USD
    Bakeries, breweries & views - oh my! With the perfect mix of outdoor adventures, local farms, and tasty bites, this is the ideal trip for your whole road trip crew. The perfect road trip for any Little Women movie fans, too!
    • Accessible
    • Kid-Friendly
  • PERFECT YEAR-ROUND
    Haunts, Hikes & History

    Haunts, Hikes & History

    Regular price $39.00 USD
    Sale
    From haunted happenings to easy strolls and historic hot spots, this trip has a little bit of everything for everyone!
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLER
    Sandhills Sauntering

    Sandhills Sauntering

    $65 USD
    Picturesque drives beneath towering trees make this an incredibly scenic trip. Sandhills Sauntering is full of epic places to eat, tons of photo-worthy moments and a hidden gem that will leave you speechless.
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • Last chance!
    Woman spinning on the beach.

    Waterside Bliss

    Regular price $39.00 USD
    Sale
    Beach breezes, coastal eats, and charming strolls await on this picturesque day trip. You’ll wander waterfront boardwalks, explore historic homes, and discover secret spots only the locals know - all with a side of sandy serenity and small-town charm.
    • Kid-Friendly
    • Dog-Friendly
  • GREAT SUMMER ROADTRIP
    Peculiar Wonders

    Peculiar Wonders

    $49 USD Sale
    Travel through time and terrain on this Alberta road trip packed with scenic strolls, quirky museums, epic photo ops, and fun for all ages. From lush gardens and lakeside boardwalks to towering trestle bridges and even free-roaming bison, this one's full of "wait, where are we?" moments—in the best way possible.
    • Kid-Friendly
    • Dog-Friendly
    Sale
  • CAN BE DONE IN WINTER
    Black and white photo of an old house.

    An Unusual Adventure

    $49 USD Sale
    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
  • A LITTLE BIT OF EVERYTHING!
    A box of assorted donuts with different toppings and glazes.

    Treats & Trails

    $65 USD
    Is there anything better than a leisurely day sipping hot coffee, enjoying tasty treats, and wandering along quiet snow-covered boardwalk trails? We think not!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • An iconic winter route
    A scenic view of a road leading towards mountains with green trees on both sides.

    Secrets on the Scenic Route

    $65 USD
    This trip blends iconic attractions with quite a few hidden gems before ending in one of the coolest villages in Canada. Snowy peaks, misty views, and quieter stops make this famous route feel extra special when explored at a slower pace.
    • Dog-Friendly
  • BEST DONE SPRING-FALL
    Valley Views

    Valley Views

    $65 USD
    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
  • BEST SELLER
    Offbeat Oddities

    Offbeat Oddities

    $65 USD
    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
  • COZY WINTER ROAD TRIP
    Covered Bridges & Baked Goods

    Covered Bridges & Baked Goods

    $65 USD
    This trip feels like stepping back in time! Wind your way along quiet country roads to picturesque covered bridges, locally owned bakeries, farmers' markets, and charming small-town shops.
    • Kid-Friendly
    • Accessible
  • CAN BE DONE IN WINTER
    Cascades & Colors

    Cascades & Colors

    $65 USD
    Funky, colorful towns filled with local eateries and shops, icy waterfalls that stop you in your tracks, and one of the most unusual gardens we’ve ever seen. You’ll definitely want your camera out for this trip!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • CAN BE DONE IN WINTER
    Vibrant Vistas & Picturesque Towns

    Vibrant Vistas & Picturesque Towns

    $65 USD
    Hit the road and explore easy outdoor adventures, outstanding views and small towns that inspired Stars Hollow in Gilmore Girls.
    • Dog-Friendly
  • BEST SELLER
    Funky Farms & Storybook Tales

    Funky Farms & Storybook Tales

    $65 USD
    It’s no wonder authors flocked to this part of Massachusetts for inspiration. Set out on a scenic drive through storybook landscapes to discover farms, boardwalk trails, quirky history, and plenty of charming surprises along the way.
    • Accessible
    • Kid-Friendly
  • BEST DONE JUNE-SEPTEMBER
    The Long and Unknown Road

    The Long and Unknown Road

    $65 USD
    If you love a long and interesting drive, this trip is for you! This trip is approximately 5 hours round-trip from Calgary, so we recommend leaving super early or extending your stay into an overnight getaway.
    • Dog-Friendly
  • GREAT YEAR-ROUND TRIP
    A person outdoors holding a camera up to their face, with a body of water and a blurred background.

    Quirky Delights

    Regular price $39.00 USD
    Sale
    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
  • ONTARIO
    Maple Syrup Farm in Winter

    Festive Edition: The Sweet & Scenic Route

    Regular price $65.00 Sale price $39.00 USD
    Sale
    A little sweet, a little scenic—this road trip blends cozy cafés, local wine, and maple treats with easy winter trails and frozen waterfalls. Perfect for a festive family road trip or romantic getaway!
    • Kid-Friendly
    • Accessible
    Sale
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!