Woman holding four Guess Where Trips envelopes while on road trip

Eastern States

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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  • Last chance!
    Mother and child walking on a winding road surrounded by greenery

    Enchanted Adventures

    $65 USD
    Around every winding road is a world of whimsical and enchanted adventures. This family-friendly trip is perfect for those who love easy trails, farm market stops, colorful photo ops and tasty treats.
    • Kid-Friendly
    Can depart from: New York City Area, Philadelphia Area, Trenton 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
  • EXPLORE CAPE COD
    Escape to the Cape

    Escape to the Cape

    $65 USD
    This road trip is full of Cape Cod charm. Think picturesque views, independent shops, heritage buildings, boardwalks and more. This trip focuses more on the hidden gems, quaint towns and history of the area.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Boston Area, Providence 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
  • 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!
    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
  • 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
    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 USD
    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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