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

  • CAN BE DONE IN WINTER
    Cascades & Colors

    Cascades & Colors

    $65 CAD
    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
  • BEST SELLER
    Red barn in a snowy landscape with bare trees.

    Funky Farms & Storybook Tales

    $65 CAD
    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
  • 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 CAD
    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 CAD
    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
    Sold out
  • last chance!
    A person standing on a trail in a forested area

    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
  • 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
  • CAN BE DONE IN WINTER
    Charming Curiosities

    Charming Curiosities

    $65 CAD
    With a few haunted tales, trails steeped in history, and charming historic mansions, this surprise road trip is full of intriguing stops and stories waiting to be uncovered.
    • Dog-Friendly
    • Kid-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
  • BEST SELLING GIFT
    Bowen Island Gems

    Bowen Island Gems

    Regular price $65.00 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
    Sold out
  • PERFECT FOR SUMMER OR FALL
    Boardwalk leading to a beach.

    Coastal Connection

    Regular price $39.00 CAD
    Sale
    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 SELLER
    Two people sitting on a rock with arms raised, enjoying a scenic view of a landscape.

    Quaint Corners

    $65 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
  • CAN BE DONE IN WINTER
    A scenic view of a waterfall surrounded by green foliage.

    Waterfall Wanderings

    $65 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
  • A COZY WINTER ROAD TRIP!
    A person holding up a sugar-coated doughnut, likely enjoyed as part of the 'A Taste of Amish Country' experience.

    A Taste of Amish Country

    $65 CAD
    Escape to the quiet charm of Amish country for cheese tastings, sweet treats, craft shops, funky museums, and incredible historic photo ops - all set against peaceful countryside scenery.
    • Kid-Friendly
    • Accessible
  • BEST DONE SPRING-FALL
    The Shore Explorer

    The Shore Explorer

    $65 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
  • Last chance!
    Mother and child walking on a winding road surrounded by greenery

    Enchanted Adventures

    $50 CAD Sale
    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, colorful photo ops and tasty treats.
    • Kid-Friendly
  • Digital Download Only
    A monument at Gettysburg, featuring a statue on top of a classical Revival dome, surrounded by an open field under a partly cloudy sky.

    Secrets of Gettysburg

    Regular price $39.00 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
  • EXPLORE CAPE COD
    Escape to the Cape

    Escape to the Cape

    $65 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
  • BEST SELLER
    Treasure Coast Explorer

    Treasure Coast Explorer

    $65 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
  • BEST SELLER
    Two woman sitting on rocks by ocean.

    Coffee, Canyons & Coastlines

    $65 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
  • CYCLE FRIENDLY
    Sunset over a river with trees in the foreground

    A Riverside Ramble

    $50 CAD Sale
    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 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
  • SCENIC ROAD TRIP
    Groves, Gardens & Grapevines

    Groves, Gardens & Grapevines

    $65 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
  • BEST SELLER
    Wonder & Whimsy

    Wonder & Whimsy

    $50 CAD Sale
    Embark on a day trip where lakeside strolls, whimsical gardens, and charming small-town shops and eateries are just the beginning. Along the way, you'll explore a quirky hotel, a few scenic sights, and even read a haunted tale or two!
    • Kid-Friendly
  • YEAR-ROUND JOY
    A festive Christmas-themed miniature village display with snow-covered houses and a large Christmas tree in the center.

    Endless Christmas Cheer

    $50 CAD Sale
    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
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

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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!