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.

Browse all trips

  • Last chance!
    A person standing among tall cactus plants in a desert landscape with mountains in the background.

    Joshua Tree Journey

    $65 USD
    Think cowboy towns, desert trails, rooftop cacti, and a whole lot of quirky charm. This road trip blends epic eats, funky photo ops and offbeat art with your journey to Joshua Tree National Park—whether it’s your first time or your fifth.
    • Dog-Friendly
    • Kid-Friendly
  • PERFECT FOR MOVIE BUFFS
    A person holding a camera and taking a photo, with a focus on the camera and the person's hand

    Cinema & Scenery

    $65 USD
    Discover hidden art, channel your inner movie star, indulge in tasty bites, and enjoy a waterside stroll. This captivating adventure offers a perfect blend of creativity, culture, and coastal charm.
    • Kid-Friendly
    • Accessible
  • 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
  • IDEAL SUMMER TRIP
    Art Trails & River Tales

    Art Trails & River Tales

    $65 USD
    A scenic road trip southeast of Minneapolis with river bluffs, small towns, and artistic stops.
    • Kid-Friendly
    • Dog-Friendly
  • OUTDOOR ADVENTURES!
    River overlook with trees beginning to change color in the fall.

    Walk on the Wild Side

    $65 USD
    From Scandinavian treats to rocky riverside hikes and a stop at a wildlife park, this photo-worthy adventure is packed with fresh air, big views, and even a tipple or two at a local winery.
    • Dog-Friendly
    • Kid-Friendly
  • last chance!
    Solvang Splendors

    Solvang Splendors

    $65 USD
    Escape to the Santa Ynez Valley and explore cute small towns, the roaming vineyard hills, local farms and so much more. We highly recommend turning this trip into a weekend adventure! 
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
  • PERFECT FAMILY ROAD TRIP!
    Bison in the middle of a grassy field and grey skies.

    Creatures & Quirks

    $65 USD
    From towering sculptures and wild bison to waterfalls, eye-spy photo ops, and pints with peacocks, this adventure is as weird and wonderful as they come!
    • Kid-Friendly
    • Accessible
  • Last chance!
    Tastes & Trails of Malibu

    Tastes & Trails of Malibu

    $65 USD
    This iconic route along the PCH is full of hidden gems and epic viewpoints. Put your walking shoes on, save room for awesome eats, and get ready to be beachside!
    • Kid-Friendly
  • CLOSE TO THE CITY!
    Gazebo overlooking a lake on a sunny day.

    Lakeside Treasures

    $65 USD
    This laid-back road trip blends small-town charm with offbeat surprises and scenic sips. Discover lakeside towns, quirky art gardens, a few furry friends, and the perfect patio pint.
    • Kid-Friendly
    • Accessible
Three women walking through tulip fields
Winding roads through mountains at sunrise

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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!