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.

Browse all trips

  • GREAT YEAR-ROUND TRIP
    Tree lined road

    A Drive Back in Time

    $65 CAD
    A relaxed Atlanta-area road trip through charming small towns, cozy cafés, and quirky photo stops.
    • Accessible
    Can depart from: Atlanta Area, Chattanooga Area
  • BEST SELLER
    Two girls sitting in back of crossover SUV.

    A Little Bit of Everything

    $65 CAD
    A well-rounded Charlotte-area road trip with local shops, a scenic rail trail, and a little bit of everything.
    • Accessible
    • Kid-Friendly
    Can depart from: Charlotte Area, Winston-Salem Area
  • Digital Only
    Woman taking photo can be seen in side view mirror of car.

    All Things Strange & Beautiful

    $39 CAD
    A unique road trip between Atlanta and Augusta with filming spots, scenic drives, and unexpected stops.
    • Accessible
    • Kid-Friendly
    Sale
    Can depart from: Atlanta Area
  • CLOSE TO ORLANDO
    Wooden boardwalk trail in a lush green forest setting

    Boardwalks, Brews & Markets

    $65 CAD
    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
    Can depart from: Orlando Area, Tampa Area, Lakeland Area, Gainesville Area
  • PERFECT YEAR-ROUND
    Haunts, Hikes & History

    Haunts, Hikes & History

    $65 CAD
    From haunted happenings to easy strolls and historic hot spots, this trip has a little bit of everything for everyone!
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area, Winchester VA Area
  • GREAT YEAR-ROUND TRIP
    A scenic view of mountains and a clear sky with clouds, framed by trees in the foreground.

    Mountain Marvels

    $65 CAD
    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
    Can depart from: Atlanta Area, Chattanooga Area
  • Great Year-Round Trip
    Ruins of an old building overgrown with trees and plants

    Mysterious Gems

    $65 CAD
    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
    Can depart from: Orlando Area, Jacksonville Area
  • BEST SELLER
    Offbeat Oddities

    Offbeat Oddities

    $65 CAD
    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
    Can depart from: Tampa Area, Orlando Area, Lakeland Area, Gainesville Area
  • Digital Only
    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
    Sale
    Can depart from: Orlando Area, Gainesville Area, Jacksonville Area
  • FANTASTIC OVERNIGHT TRIP
    A person taking a photo with a smartphone from a car, capturing a scenic view.

    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
    Can depart from: Charlotte Area, Winston-Salem Area
  • 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 depart from: Atlanta Area, Macon Area, Columbus Area, LaGrange Area
  • Road Trip Gift Card

    Road Trip Gift Card

    $74.00 CAD
    Give the gift of a one-day surprise road trip with Guess Where Trips®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire.
  • BEST SELLER
    Man walking through a forest on a dirt path

    Sandhills Sauntering

    $65 CAD
    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
    Can depart from: Raleigh Area
  • 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
    Can depart from: Orlando Area, Jacksonville Area, Gainesville Area
  • 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

    $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
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area, Winchester VA Area
  • 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
    Can depart from: Fort Myers Area, Naples Area, Tampa Area
  • DIGITAL ONLY
    Woman spinning on the beach.

    Waterside Bliss

    $39.00 CAD
    Beach breezes, coastal eats, and charming strolls await on this picturesque day trip. You’ll wander waterfront boardwalks, explore historic homes, and discover secret spots only the locals know - all with a side of sandy serenity and small-town charm.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area
  • GREAT FOR A WEEKEND AWAY
    Winding Roads & Historic Gems

    Winding Roads & Historic Gems

    $65 CAD
    Discover photo-worthy hidden gems along winding roads as you make your way to an iconic road trip destination filled with history and views.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
    Can depart from: Washington DC Area, Baltimore Area, Winchester VA Area, Alexandria VA Area
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!