Woman holding four Guess Where Trips envelopes while on road trip

South

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 YEAR-ROUND TRIP
    Tree lined road

    A Drive Back in Time

    $39 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
  • 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
  • OFF-THE-BEATEN-PATH ROAD TRIP
    Woman taking photo can be seen in side view mirror of car.

    All Things Strange & Beautiful

    $39 USD
    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
  • SOMETHING FOR EVERYONE
    Park bench and fountain at the end of a brick path in a garden.

    Antique Adventures

    $39 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 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
  • PERFECT YEAR-ROUND
    Haunts, Hikes & History

    Haunts, Hikes & History

    $39 USD
    From haunted happenings to easy strolls and historic hot spots, this trip has a little bit of everything for everyone!
    • Kid-Friendly
    • Dog-Friendly
  • GREAT FALL TRIP
    Mountain Marvels

    Mountain Marvels

    $39 USD
    This family-friendly trip is the ultimate way to escape the city and head to the mountains. Stroll the streets of charming small towns, explore quirky art and museums, indulge in tasty bites & brews and enjoy the surprise!
    • Accessible
    • Kid-Friendly
  • 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
  • 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
  • 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
  • FANTASTIC OVERNIGHT TRIP
    Picture Perfect Discoveries

    Picture Perfect Discoveries

    $39 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
  • BEST SELLER
    Quaint Corners

    Quaint Corners

    $39 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
  • 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
    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
  • GREAT OVERNIGHT TRIP
    Seaside Legends

    Seaside Legends

    $39 USD
    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
  • GREAT FALL TRIP
    The Road to Asheville

    The Road to Asheville

    $39 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
  • BEST SELLER
    The Southwest Quest

    The Southwest Quest

    $39 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
  • A CLOSE TO HOME ADVENTURE
    Timeless Towns & Scenic Sips

    Timeless Towns & Scenic Sips

    $39 USD
    Brews, bites and a whole lot of history! From small town charm to tasty tipples and one of the most unique (and eerie) trails we've ever found, this road trip has something for everyone.
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • BEST SELLER
    Treasure Coast Explorer

    Treasure Coast Explorer

    $39 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
  • GREAT WEEKEND TRIP
    Wacky Wonders

    Wacky Wonders

    $39 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.
  • 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
    Whimsical Wonders

    Whimsical Wonders

    $39 USD
    Escape to hidden gem destinations that make you feel like you've stepped into a fairytale world. Lucious gardens, charming towns and whimsical photo ops make this the perfect road trip.
    • Kid-Friendly
    • Accessible
  • GREAT FALL TRIP
    Winding Roads & Historic Gems

    Winding Roads & Historic Gems

    $39 USD
    Discover photo-worthy hidden gems along winding roads as you make your way to an iconic road trip destination.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
Three women walking through tulip fields
Winding roads through mountains at sunrise

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