Woman holding four Guess Where Trips envelopes while on road trip

United 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!
    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
  • GREAT SUMMER ROADTRIP
    A sandy trail leading to the water

    Lakeshore Views & Brews

    $65 USD
    Stroll along a breathtaking boardwalk, dip your does in the cool water, sip craft drinks in unique destinations, and take lots of funky photos! This road trip will certainly let you unwind from the hustle and bustle of the city.
    • Kid-Friendly
    • Accessible
  • 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
  • FOR THE FOODIES
    Woman running along oceanside.

    Birds, Breezes & Cheeses

    $65 USD
    Say cheese! That's right, we've rounded up the best cheese shops and the most photo-worthy moments a road trip can have. You'll feel the breeze in your hair as you walk down coastal trails and quaint streets.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • 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
  • Last chance!
    Medieval castle-like stone structure with a clear blue sky in the background.

    Storybook Strolls

    $65 USD
    A day full of whimsy, wonder and quirky destinations that will make you feel like you're living in a storybook world. This trip is perfect for the whole road trip crew, from families with kids to girlfriend getaways!
    • Kid-Friendly
  • CYCLE FRIENDLY
    Ojai Oasis

    Ojai Oasis

    $65 USD
    Small-town charm is at the center of this Ojai road trip. Shop 'till you drop, indulge in local wine and sweet treats, and meander along a few short trails. This trip is cycle-friendly too!
    • Accessible
    • Dog-Friendly
  • Last chance!
    View from inside a wooden covered bridge looking out at a tree-lined road leading to a bright sky.

    Bridges & Beauty

    $65 USD
    Get ready to wind your way through scenic tree-lined roads, cross charming covered bridges, sip at cozy wineries, hike stunning trails, and maybe even get a chill from a ghostly tale or two.
    • Accessible
    • Kid-Friendly
    • Dog-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 OVERNIGHT GETAWAY
    Grassy landscape with hills.

    Country Treasures

    $65 USD
    Escape to the country and visit tons of charming bakeries, get your steps in on easy trails, sip something tasty, and end the day in the most amazing small town.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • last chance!
    Rivers & Rural Roads

    Rivers & Rural Roads

    $50 USD Sale
    Riverside roaming strolls, historic highlights, scenic spots for sipping wine or beer, and some of the prettiest rural roads are just a few of the hidden gems you’ll discover on this trip!
    • Kid-Friendly
  • Last chance!
    A thematic setup featuring items related to witchcraft and Halloween, including pumpkins, candles, books, and various decorative elements on a table.

    Witchy Wonders

    $65 USD
    This road trip will have you exploring the Salem witch trials, haunted history and a few iconic Hocus Pocus locations. This trip can be done throughout the year. If you're travelling during the month of October some attractions need to be pre-booked as the area gets significantly busier.
    • Accessible
    • Kid-Friendly
  • 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
  • A LEISURELY ROAD TRIP
    Woman hiking in a forest

    Woodland Walks & Wineries

    $65 USD
    Funky forest finds are on every stop, which are perfect for the outdoor adventurer. Unique wineries, bakeries, and a museum celebrating a man we have a lot to thank for are sprinkled in for the more leisurely road tripper.
    • Kid-Friendly
  • FOR COUNTRYSIDE DRIVES
    Cozy Country Charm

    Cozy Country Charm

    $65 USD
    The perfect blend of rustic allure, cute small towns, cozy cafes, and farmstead feelings makes this a fantastic road trip for those looking to slow down and appreciate the little moments.
    • Kid-Friendly
    • Accessible
  • SPOOKY STORIES
    Eerie Escapes

    Eerie Escapes

    $65 USD
    Step into a day where every stop sends a shiver down your spine. Ghostly whispers in cemeteries, abandoned ruins, and wooded trails full of chilling stories will leave you wondering if any spirits followed you home.
    • Dog-Friendly
    • Accessible
  • EXPLORE AN ICONIC AREA
    A red covered bridge crossing a rocky stream, surrounded by green forest.

    Countless Covered Bridges

    $65 USD
    Take a leisurely drive through the idyllic countryside, hopping from one quaint covered bridge to another. We've sprinkled in a few local eateries and easy trails to give your camera a break! 
    • Dog-Friendly
    • Kid-Friendly
  • Last chance!
    South Bay Secrets

    South Bay Secrets

    $65 USD
    Coastal walks and lighthouse views make this South Bay road trip incredibly picturesque. It's the perfect choice for a trip close to home!
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • FAMILY FRIENDLY
    Colorful houses along a beach.

    Colors & Wonders

    $65 USD
    This trip is full of colorful wonders - like a short hike to get your heart rate up before you relax with an afternoon beverage, support a local shop, or sip coffee & indulge in delicious baked goods.
    • 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
  • EPIC VIEWS
    Ocean photographed from atop a hill.

    Down by the Bay

    $65 USD
    You don't have to go far from home to have an epic adventure! The scenic viewpoints and easy trails are endless on this trip. And while you won't see watermelons grow, there are tons of fantastic local eateries along the way.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
  • FOR THE PHOTOGRAPHER
    Elegant Estates & Outdoor Art

    Elegant Estates & Outdoor Art

    $65 USD
    Just a short drive from Indy, you'll find a world full of elegant estates, whimsical gardens, and colorful outdoor art. We'll tell you all of the quirky fun facts and historic moments that make these spots so unique!
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
  • Last chance!
    Two people toasting with glasses of wine, set against a wallpaper with a tropical leaf pattern.

    Sonoma Sips & Strolls

    $65 USD
    Scenic sipping and picturesque strolls can be found in this iconic area of California! We've found hidden gem wineries, tasty food shops, a few easy trails and so much more.
    • Dog-Friendly
    • Accessible
Three women walking through tulip fields
Winding roads through mountains at sunrise

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