Woman holding four Guess Where Trips envelopes while on road trip

Home - Southern USA

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
    A scenic view of mountains and a clear sky with clouds, framed by trees in the foreground.

    Mountain Marvels

    $65 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
  • Digital Only
    Woman taking photo can be seen in side view mirror of car.

    All Things Strange & Beautiful

    $39 USD
    A unique road trip between Atlanta and Augusta with filming spots, scenic drives, and unexpected stops.
    • Accessible
    • Kid-Friendly
    Sale
  • GREAT FOR FAMILIES
    Quirky & Colorful

    Quirky & Colorful

    $65 USD
    From charming coffee spots and hidden gardens to quirky museums and haunted tales, this adventure has something unexpected at every turn. Top it all off with shopping, murals, and more in one of Texas’ most vibrant small towns!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • LAST CHANCE
    Strange & Spooky Sights

    Strange & Spooky Sights

    $65 USD
    Get ready for a spine-tingling adventure as you explore some of the most haunted and historic spots in the state. Along the way, you'll encounter restaurants and cafes with ghostly legends, strange stories, peculiar museums and haunted objects galore — perfect for anyone who loves a good thrill mixed with quirky charm!
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • GREAT FOR FOODIES!
    Cowboy Country Crawl

    Cowboy Country Crawl

    $65 USD
    Saddle up for a Wild West adventure packed with charm. Snap a few cowboy-inspired photos, savor local flavors, and cool off at a hidden swimming hole. It’s everything you need for an unforgettable day in cowboy country!
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • AN ICONIC ROUTE
    Hill Country Harvest

    Hill Country Harvest

    $65 USD
    Embark on a day of scenic sips and charming discoveries! With visits to stunning wineries, a renowned distillery, a beautiful wildflower farm, and photogenic roadside stops, this is the perfect getaway to explore the best of Hill Country's iconic Highway 290.
    • Accessible
    • Kid-Friendly
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

Take Our Quiz to Find Out

Select your region and interests to find the best trip for you.

Take the Quiz
Woman on road trip leaning out window

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!