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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  • GREAT SUMMER ROADTRIP
    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
    Secrets of Gettysburg

    Secrets of Gettysburg

    $65 USD
    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
  • CLOSE TO ORLANDO
    Boardwalks, Brews & Markets

    Boardwalks, Brews & Markets

    $65 USD
    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 USD
    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
  • BEST SELLER
    Quaint Corners

    Quaint Corners

    $65 USD
    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
  • A CLOSE TO HOME ADVENTURE
    Charming Curiosities

    Charming Curiosities

    $65 USD
    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 SELLER
    The Southwest Quest

    The Southwest Quest

    $65 USD
    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 SUMMER OR FALL
    Boardwalk leading to a beach.

    Coastal Connection

    $65 USD
    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
  • GREAT SUMMER ROADTRIP
    The Shore Explorer

    The Shore Explorer

    $65 USD
    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 SELLER
    Treasure Coast Explorer

    Treasure Coast Explorer

    $65 USD
    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
  • FOR THE OUTDOOR ADVENTURER
    Waterfall Wanderings

    Waterfall Wanderings

    $65 USD
    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
  • PERFECT FOR FAMILIES
    Enchanted Adventures

    Enchanted Adventures

    $65 USD
    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
  • EXPLORE CAPE COD
    Escape to the Cape

    Escape to the Cape

    $65 USD
    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

    $65 USD
    Escape to quintessential Amish country for cheese tastings, sweet treats, craft shops, funky museums and some incredible historic photo ops.
    • Kid-Friendly
    • Accessible
  • BEST SELLER
    Two woman sitting on rocks by ocean.

    Coffee, Canyons & Coastlines

    $65 USD
    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
  • SCENIC ROAD TRIP
    Groves, Gardens & Grapevines

    Groves, Gardens & Grapevines

    $65 USD
    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
    Sale
  • GREAT OVERNIGHT GETAWAY!
    The Road to Asheville

    The Road to Asheville

    $65 USD
    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
  • GREAT FOR ACTIVE FAMILIES
    Sweet Sensations

    Sweet Sensations

    $65 USD
    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
  • GREAT YEAR-ROUND TRIP
    Tree lined road

    A Drive Back in Time

    $65 USD
    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
  • FANTASTIC OVERNIGHT TRIP
    Picture Perfect Discoveries

    Picture Perfect Discoveries

    $65 USD
    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
  • YEAR-ROUND JOY
    Endless Christmas Cheer

    Endless Christmas Cheer

    USD
    This is the perfect trip for those of you who think that extra-festive feeling should be a year-round experience. Decorations, cozy wine stops, and covered bridges - oh my!
    • Kid-Friendly
    • Accessible
    Sold out
  • CAN BE DONE IN WINTER
    A Riverside Ramble

    A Riverside Ramble

    $65 USD
    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
  • SOMETHING FOR EVERYONE
    Park bench and fountain at the end of a brick path in a garden.

    Antique Adventures

    $65 USD
    This leisurely trip packs a punch! Expect a variety of antique shops (both small and large), cozy cafes, funky eateries, effortless outdoor escapades and haunted stops along the way. The best part? It's only a quick jaunt from the city.
    • Accessible
  • GREAT WEEKEND TRIP
    Wacky Wonders

    Wacky Wonders

    $65 USD
    A little funky, a little unexpected, and totally unforgettable—this road trip is a whirlwind of colorful folk art, quirky roadside stops, scenic detours, and bites worth savoring. The only rule? Embrace the unexpected.
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!