Woman holding four Guess Where Trips envelopes while on road trip

Southeast

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

  • 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
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    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
  • 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
  • FATHER'S DAY PICK
    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
  • 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
  • BEST SELLER
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    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
  • 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
  • BEST SELLER
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    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
  • 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
  • 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
  • FANTASTIC OVERNIGHT TRIP
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    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
  • 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
  • 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
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!