Woman holding four Guess Where Trips envelopes while on road trip

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Select a trip that works with your driving and travel preferences. If it's hard to choose, take our road trip quiz instead.

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  • BEST DONE JUNE-SEPTEMBER
    The Long and Unknown Road

    The Long and Unknown Road

    $65 CAD
    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
  • BEST SELLING GIFT
    Old Florida Trail

    Old Florida Trail

    $39 CAD
    Go back in time and visit old Florida. You'll visit delightful small towns, dig into local fare, explore a few outdoor adventures, and fill up your camera roll with quirky photo ops.
    • Kid-Friendly
  • Great Year-Round Trip
    Mysterious Gems

    Mysterious Gems

    $39 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
  • CLOSE TO ORLANDO
    Boardwalks, Brews & Markets

    Boardwalks, Brews & Markets

    $39 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
  • LAST CHANCE
    Secrets of Gettysburg

    Secrets of Gettysburg

    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
    Sold out
  • BEST SELLER
    Two girls sitting in back of crossover SUV.

    A Little Bit of Everything

    $39 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
  • CAN BE DONE IN WINTER
    Charming Curiosities

    Charming Curiosities

    $39 CAD
    With a few haunted stories, trails with a unique past, and charming historic mansions, we're confident you'll find new favorite spots to explore when you hit the road with this surprise trip.
    • Dog-Friendly
    • Kid-Friendly
    • Accessible
  • BEST SELLING GIFT
    Quaint Corners

    Quaint Corners

    $39 CAD
    Cozy cafes, countryside drives, gorgeous lookouts and quirky roadside stops are just some of the things you'll discover on your surprise road trip!
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
  • PERFECT FOR SUMMER OR FALL
    Boardwalk leading to a beach.

    Coastal Connection

    $39 CAD
    From seaside strolls and spooky ruins to cider donuts and historic mansions, this charming coastal road trip is full of surprises. Whether you’re wandering a 17th-century town green, petting goats at a giant book barn, or soaking in saltwater views, you’ll fall in love with Connecticut’s quirkier side.
    • Dog-Friendly
    • Accessible
    • Kid-Friendly
  • BEST DONE SPRING-FALL
    The Shore Explorer

    The Shore Explorer

    $39 CAD
    Hop from shore to shore on this iconic beachside road trip just a short drive from the tri-state area. Alongside beaches, you'll also explore waterside boardwalks, age-old lighthouses, scenic viewpoints, and delicious local eateries.
    • Dog-Friendly
    • Accessible
    • Kid-Friendly
  • BEST SELLING GIFT
    The Southwest Quest

    The Southwest Quest

    $39 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
  • PERFECT FOR FAMILIES
    Enchanted Adventures

    Enchanted Adventures

    $39 CAD
    Around every winding road is a world of whimsical and enchanted adventures. This family-friendly trip is perfect for those who love easy trails, farm market stops, colourful photo ops and tasty treats.
    • Kid-Friendly
  • CAN BE DONE IN WINTER
    Waterfall Wanderings

    Waterfall Wanderings

    $39 CAD
    The ultimate waterfall adventure not too far from home! Wander along historic paths, snap photos of four falls, enjoy a glass of local vino and explore a mysterious cave.
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLING GIFT
    Treasure Coast Explorer

    Treasure Coast Explorer

    $39 CAD
    We've recommended our favourite hidden gems within this iconic area of Florida. Beach hopping, easy walks, charming cafes, and historic spots. This trip really does have it all!
    • Accessible
    • Kid-Friendly
  • EXPLORE CAPE COD
    Escape to the Cape

    Escape to the Cape

    $39 CAD
    This road trip is full of Cape Cod charm. Think picturesque views, independent shops, heritage buildings, boardwalks and more. This trip focuses more on the hidden gems, quaint towns and history of the area.
    • Kid-Friendly
    • Dog-Friendly
  • TONS OF TASTY BITES + SHOPS
    A Taste of Amish Country

    A Taste of Amish Country

    $39 CAD
    Escape to quintessential Amish country for cheese tastings, sweet treats, craft shops, funky museums and some incredible historic photo ops.
    • Kid-Friendly
    • Accessible
  • GREAT FOR ACTIVE FAMILIES
    Sweet Sensations

    Sweet Sensations

    $39 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
  • SCENIC ROAD TRIP
    Groves, Gardens & Grapevines

    Groves, Gardens & Grapevines

    $39 CAD
    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
  • MICHIGAN
    Endless Christmas Cheer

    Endless Christmas Cheer

    $39 CAD
    This is the perfect trip for anyone who thinks that extra festive feeling should be a year-round experience. Decorations, cozy shops and eateries, and a picture-perfect covered bridge - oh my!
    • Kid-Friendly
    • Accessible
  • BEST SELLER
    Two woman sitting on rocks by ocean.

    Coffee, Canyons & Coastlines

    $39 CAD
    Coffee, Canyons & Coastlines - Oh my! Get your caffeine fix throughout the day to prepare for beachside moments and easy outdoor adventures. This is the perfect trip close to San Diego!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • GREAT YEAR-ROUND TRIP
    Tree lined road

    A Drive Back in Time

    $39 CAD
    The perfect day for the more leisurely road tripper. A Drive Back in Time isn't too far from the city and is full of cute towns, cafes, funky photo ops and so much more.
    • Accessible
  • CAN BE DONE IN WINTER
    Picture Perfect Discoveries

    Picture Perfect Discoveries

    $39 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
  • Which Way? A Surprise Road Trip Card Game

    Which Way? A Surprise Road Trip Card Game

    Regular price $22.00 CAD
    A surprise road trip game where the entire point is to get lost!
  • CYCLE FRIENDLY
    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
Three women walking through tulip fields
Winding roads through mountains at sunrise

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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!