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.

Browse all trips

  • Road Trip Gift Card

    Road Trip Gift Card

    Regular price $74.00 CAD
    Give the gift of a one-day surprise road trip with Guess Where Trips®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire.
  • CAN BE DONE IN WINTER
    Waterfall Wanderings

    Waterfall Wanderings

    $39 CAD
    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
  • TONS OF TASTY BITES + SHOPS
    A Taste of Amish Country

    A Taste of Amish Country

    $39 CAD
    Escape to quintessential Amish country for cheese tastings, sweet treats, craft shops, funky museums and some incredible historic photo ops.
    • Kid-Friendly
    • Accessible
  • SCENIC ROUTE
    Bridges & Beauty

    Bridges & Beauty

    $39 CAD
    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

    $39 CAD
    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
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!