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

  • 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 SELLER
    Quaint Corners

    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
  • 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
  • A CLOSE TO HOME ADVENTURE
    Charming Curiosities

    Charming Curiosities

    $65 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
  • CAN BE DONE YEAR-ROUND
    Explore the Shore

    Explore the Shore

    CAD
    This 'mini road trip' offers up quite a few adventures within North Vancouver. Perfect for families, and roadtrippers who don't want to venture too far away from home. Discover your new favourite farm, beach or cafe while you 'Explore the Shore'.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
    Sold out
  • explore beach towns
    Boardwalk leading to a beach.

    Coastal Connection

    $65 CAD
    Feel the ocean breeze in your hair as you go from beaches and boardwalks to independent shops and eateries. There are a few unusual surprises in this trip that will keep you on your toes! This is a great trip to do from the New Haven and Hartford area.
    • Dog-Friendly
    • Accessible
    • Kid-Friendly
  • 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
  • FOR THE OUTDOOR ADVENTURER
    Waterfall Wanderings

    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
  • 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
  • Perfect for Families
    Enchanted Adventures

    Enchanted Adventures

    $65 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
  • TONS OF TASTY BITES & SHOPS
    A Taste of Amish Country

    A Taste of Amish Country

    $65 CAD
    Escape to quintessential Amish country for cheese tastings, sweet treats, craft shops, funky museums and some incredible historic photo ops.
    • Kid-Friendly
    • Accessible
  • THE ULTIMATE WEEKEND TRIP
    The Road to Asheville

    The Road to Asheville

    CAD
    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
    Sold out
  • GREAT YEAR-ROUND TRIP
    Tree lined road

    A Drive Back in Time

    $65 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
  • FOR HOLLY JOLLY FEELINGS
    Endless Christmas Cheer

    Endless Christmas Cheer

    $55 CAD Sale
    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
    Sale
  • FANTASTIC OVERNIGHT TRIP
    Picture Perfect Discoveries

    Picture Perfect Discoveries

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

    Antique Adventures

    $65 CAD
    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
  • 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
  • OFF-THE-BEATEN-PATH ROAD TRIP
    Woman taking photo can be seen in side view mirror of car.

    All Things Strange & Beautiful

    $65 CAD
    A few famous filming spots, scenic drives, local eateries and an eerie abandoned area are just some of the strange and beautiful things you'll discover on this road trip.
    • Accessible
    • Kid-Friendly
  • SCENIC ROAD TRIP
    Groves, Gardens & Grapevines

    Groves, Gardens & Grapevines

    $55 CAD Sale
    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 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
  • CAN BE DONE IN WINTER
    A Riverside Ramble

    A Riverside Ramble

    $65 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
  • GREAT WEEKEND TRIP
    Wacky Wonders

    Wacky Wonders

    $65 CAD
    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.
  • GREAT OVERNIGHT TRIP
    Seaside Legends

    Seaside Legends

    $65 CAD
    Little local legends are sprinkled throughout your day, telling the story of an iconic area of Florida. Expect picturesque beaches, tasty eats, a historic city, and so much more.
    • Kid-Friendly
    • Dog-Friendly
  • EXPLORE SALEM
    Witchy Wonders

    Witchy Wonders

    $65 CAD
    This road trip will have you exploring the Salem witch trials, haunted history and a few iconic Hocus Pocus locations. This trip can be done throughout the year. If you're travelling during the month of October some attractions need to be pre-booked as the area gets significantly busier.
    • Accessible
    • Kid-Friendly
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!