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

  • BEST SELLER
    A person standing at the entrance of a lush garden pathway, looking towards the light at the end of the tunnel created by the archway.

    Whimsical Wonders

    $65 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
    Can depart from: Philadelphia Area, Trenton Area, Baltimore Area
  • GREAT FOR A WEEKEND AWAY
    Winding Roads & Historic Gems

    Winding Roads & Historic Gems

    $65 USD
    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
  • PERFECT YEAR-ROUND
    Haunts, Hikes & History

    Haunts, Hikes & History

    $65 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
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area, Winchester VA Area
  • DIGITAL ONLY
    Woman spinning on the beach.

    Waterside Bliss

    $39.00 USD
    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
  • BEST SELLER
    Man walking through a forest on a dirt path

    Sandhills Sauntering

    $65 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
    Can depart from: Raleigh Area
  • BEST SELLER
    Offbeat Oddities

    Offbeat Oddities

    $65 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
    Can depart from: Tampa Area, Orlando Area, Lakeland Area, Gainesville Area
  • CLOSE TO ORLANDO
    Wooden boardwalk trail in a lush green forest setting

    Boardwalks, Brews & Markets

    $65 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
    Can depart from: Orlando Area, Tampa Area, Lakeland Area, Gainesville Area
  • GREAT YEAR-ROUND TRIP
    A person outdoors holding a camera up to their face, with a body of water and a blurred background.

    Quirky Delights

    $65 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
    Can depart from: Winston-Salem Area, Raleigh Area
  • Digital Only
    A person standing on a trail in a forested area

    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
    Sale
    Can depart from: Orlando Area, Gainesville Area, Jacksonville Area
  • BEST SELLER
    Two girls sitting in back of crossover SUV.

    A Little Bit of Everything

    $65 USD
    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 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
    Can depart from: Fort Myers Area, Naples Area, Tampa Area
  • BEST SELLER
    Two people sitting on a rock with arms raised, enjoying a scenic view of a landscape.

    Quaint Corners

    $65 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
    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 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
    Can depart from: Orlando Area, Jacksonville 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 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
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area, Winchester VA Area
  • BEST SELLER
    Treasure Coast Explorer

    Treasure Coast Explorer

    $65 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
    Can depart from: West Palm Beach Area, Miami / Fort Lauderdale Area
  • GREAT YEAR-ROUND TRIP
    Tree lined road

    A Drive Back in Time

    $65 USD
    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
    Wonder & Whimsy

    Wonder & Whimsy

    $65 USD
    Embark on a day trip where lakeside strolls, whimsical gardens, and charming small-town shops and eateries are just the beginning. Along the way, you'll explore a quirky hotel, a few scenic sights, and even read a haunted tale or two!
    • Kid-Friendly
    Can depart from: Dallas Area, Fort Worth Area
  • GREAT WEEKEND TRIP
    A person with a camera exploring a forested area

    Wacky Wonders

    $65 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.
    Can depart from: Atlanta Area, Athens Area
  • GREAT OVERNIGHT TRIP
    Seaside Legends

    Seaside Legends

    $65 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
    Can depart from: Orlando Area, Jacksonville Area, Gainesville Area
  • A CLOSE TO HOME ADVENTURE
    Timeless Towns & Scenic Sips

    Timeless Towns & Scenic Sips

    $65 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
    Can depart from: Raleigh Area, Winston-Salem Area
  • FANTASTIC OVERNIGHT TRIP
    A person taking a photo with a smartphone from a car, capturing a scenic view.

    Picture Perfect Discoveries

    $65 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
    Can depart from: Charlotte Area, Winston-Salem Area
  • LAST CHANCE
    Pretty Little Finds

    Pretty Little Finds

    $65 USD
    With plenty of picture-perfect moments, quirky stops, and a bit of everything from bees to barns, this adventure promises the perfect blend of beauty and cozy vibes. Think funky florals, farm-fresh finds and plenty of antiques!
    • Kid-Friendly
    • Accessible
    Can depart from: Austin Area, Houston Area, San Antonio Area
  • Last chance!
    A person standing in front of a colorful graffiti-covered wall.

    The Road to Asheville

    $65 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
    Can depart from: Charlotte Area, Winston-Salem Area
  • Last chance!
    Park bench and fountain at the end of a brick path in a garden.

    Antique Adventures

    $65 USD
    A Charlotte-area road trip with antique shops, cafés, and a mix of unique and slightly spooky stops.
    • Accessible
    Can depart from: Charlotte Area, Winston-Salem Area
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!