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Day Trips in Wisconsin

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

    $80.00 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.
  • CYCLE FRIENDLY
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    A Riverside Ramble

    $50 CAD Sale
    Wander through colorful sculptures, charming boutiques, and local eateries before discovering breathtaking riverside gems that are so photo-worthy, your camera roll is sure to fill up!
    • Accessible
    • Kid-Friendly
    Can depart from: Chicago Area, Milwaukee Area
  • HALLMARK MOVIE VIBES!
    All Things Charming

    All Things Charming

    $65 CAD
    From snow-dusted lakeside views and quaint small-town charm to playful animal encounters and a whimsical museum, this captivating road trip promises unforgettable moments for everyone in your group.
    • Kid-Friendly
    Can depart from: Chicago Area, Milwaukee Area
  • PERFECT FOR MOVIE BUFFS
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    Cinema & Scenery

    $65 CAD
    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
    Can depart from: Chicago Area, Milwaukee Area
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Winding roads through mountains at sunrise

CAN'T DECIDE?

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Select your region and interests to find the best trip for you.

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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!