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 SELLER
    Sandhills Sauntering

    Sandhills Sauntering

    $39 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
  • THE PERFECT FALL ROAD TRIP
    Butter Tarts, Boos & Brews

    Butter Tarts, Boos & Brews

    $65 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
  • GREAT FALL TRIP
    Vintage Vibes & Views

    Vintage Vibes & Views

    $39 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
  • BEST DONE SPRING-FALL
    Waterside Bliss

    Waterside Bliss

    $39 USD
    Boardwalks, beaches and bites make this charming itinerary the ultimate road trip!
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLER
    Scenic Sights & Tasty Bites

    Scenic Sights & Tasty Bites

    $39 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
  • BEST DONE JUNE-SEPTEMBER
    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
  • FOR THE PARANORMAL EXPLORER
    Black and white photo of an old house.

    An Unusual Adventure

    $39 USD
    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
  • GREAT SUMMER ROADTRIP
    Peculiar Wonders

    Peculiar Wonders

    $65 USD
    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
  • 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
    Bowen Island Gems

    Bowen Island Gems

    Regular price $65.00 USD
    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
  • BEST SELLER
    Offbeat Oddities

    Offbeat Oddities

    $39 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
  • An iconic route
    Secrets on the Scenic Route

    Secrets on the Scenic Route

    $65 USD
    This trip combines iconic attractions and quite a few hidden gems before ending in one of the coolest villages in Canada. Can you guess where? Perfect for those wanting to explore this famous route in more detail.
    • Dog-Friendly
  • GREAT FALL TRIP
    Treats & Trails

    Treats & Trails

    $39 USD
    Is there anything better than a leisurely day sipping coffee, enjoying tasty treats and meandering along easy boardwalk trails? We think not!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • GREAT FALL TRIP
    Red covered bridge over water.

    Covered Bridges & Baked Goods

    $39 USD
    This trip is like taking a step back in time! Wind your way through the peaceful countryside to a number of quaint covered bridges and locally owned bakeries, farmers markets, and shops.
    • Kid-Friendly
    • Accessible
  • GREAT YEAR-ROUND TRIP
    Vibrant Vistas & Picturesque Towns

    Vibrant Vistas & Picturesque Towns

    $39 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

    $39 USD
    It's no wonder authors flocked to this area of Massachusetts for inspiration! Head out on a picturesque drive and discover farms, boardwalk trails, lots of quirky history and much more.
    • Accessible
    • Kid-Friendly
  • GREAT FALL TRIP
    Quirky Delights

    Quirky Delights

    $39 USD
    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
  • BEST SELLER
    Old Florida Trail

    Old Florida Trail

    $39 USD
    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 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
  • SOMETHING FOR EVERYONE
    Cascades & Colors

    Cascades & Colors

    $39 USD
    Funky colorful towns full of local eateries and shops, a few waterfalls that will leave you in awe and one of the most unusual gardens we have ever seen. You’ll want to get your camera out for this trip!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • LAST CHANCE
    Secrets of Gettysburg

    Secrets of Gettysburg

    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
    Sold out
  • Great Year-Round Trip
    Mysterious Gems

    Mysterious Gems

    $39 USD
    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
  • GREAT FALL TRIP
    Boardwalks, Brews & Markets

    Boardwalks, Brews & Markets

    $39 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

    $39 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
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!