Woman holding four Guess Where Trips envelopes while on road trip

Cleveland Area

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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  • TONS OF TASTY BITES + SHOPS
    A person holding up a sugar-coated doughnut, likely enjoyed as part of the 'A Taste of Amish Country' experience.

    A Taste of Amish Country

    $65 USD
    A peaceful road trip near Akron through Amish country with food stops, shops, and scenic countryside.
    • Kid-Friendly
    • Accessible
    Can depart from: Cleveland Area, Columbus Area
  • FOR THE OUTDOOR ADVENTURER
    A scenic view of a waterfall surrounded by green foliage.

    Waterfall Wanderings

    $65 USD
    The ultimate waterfall adventure not too far from home! Wander along historic paths, snap photos of four falls, enjoy a glass of local vino and explore a mysterious cave.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Cleveland Area
  • 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
    Can depart from: Cleveland Area
  • 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
    Can depart from: Cleveland Area, Toledo Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

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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!