Woman holding four Guess Where Trips envelopes while on road trip

Our Trips

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

  • THE PERFECT SUMMER ROAD TRIP
    Rivers & Rural Roads

    Rivers & Rural Roads

    $65 USD
    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
  • 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
  • Returns Sept. 9!
    Witchy Wonders

    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
    Sale
  • GREAT YEAR-ROUND TRIP
    Mountain Marvels

    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
  • 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
  • WHIMSICAL ADVENTURE
    Storybook Strolls

    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
  • CLOSE TO ATLANTA
    Film & Food Crawl

    Film & Food Crawl

    $65 USD
    Georgia is often called the "Hollywood of the South" so we've rounded up a few of our favorite filming spots. Local cafes, breweries, eateries and farmers markets are also sprinkled in to keep your energy up!
    • Accessible
    Sale
  • Dog-Friendly Trip!
    Falls, Forests & Fables

    Falls, Forests & Fables

    $65 USD
    Get ready for a day filled with charm and easy outdoor adventures. Start in a small town bursting with colorful murals, then enjoy riverside lookouts and even some surprising wildlife. This trip is perfect for those who love to stay active while exploring!
    • Dog-Friendly
    • Kid-Friendly
  • GREAT SUMMER ROADTRIP
    Lakeshore Views & Brews

    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
  • GREAT WEEKEND GETAWAY
    Man standing on a road looking up among towering trees

    Forests & Funky Finds

    $65 USD
    This trip is the perfect overnight getaway! As you're driving through the woods, you'll hop between the cutest small towns full of charming shops and eateries.
    • Kid-Friendly
    • Dog-Friendly
  • GREAT YEAR-ROUND TRIP
    Outback Oasis

    Outback Oasis

    $65 USD
    The perfect combination of easy outdoor adventures, browsing through farm markets, and enjoying a slower pace. You'll feel so at ease by the end of your road trip!
    • Accessible
    • Kid-Friendly
  • SCENIC ROUTE
    Bridges & Beauty

    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
  • 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
  • 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
  • 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
  • Returns Sept. 9!
    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
  • CLOSE TO LA
    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
  • EXPLORE AN ICONIC AREA
    Countless Covered Bridges

    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
  • GREAT YEAR-ROUND TRIP
    Woman looking up through binoculars.

    Adventure in the Glades

    $65 USD
    Scenic views, unique boardwalks and funky roadside attractions can all be found when you escape to the Everglades. Just make sure you keep your eyes peeled for those pesky gators!
    • Accessible
  • GREAT YEAR-ROUND TRIP
    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
  • 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
  • Perfect Weekend Getaway!
    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
  • 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
  • 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
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!