Wisconsin

Choose a road trip that suits your driving and travel preferences from our selection below. Can't decide? Take our road trip quiz for personalized recommendations.

How does it work?

Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.

See our road trips below, or check out our quiz and trip map to help find your perfect adventure.

  • Road Trip Gift Card

    Road Trip Gift Card

    $74.00 USD
    Give the gift of a one-day surprise road trip with Guess Where Trips®! The recipient can then choose a surprise trip that suits them!
  • CYCLE FRIENDLY
    A Riverside Ramble

    A Riverside Ramble

    $39 USD
    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
  • GREAT FOR FAMILIES
    All Things Charming

    All Things Charming

    $39 USD
    From serene lakeside views and quaint small town charm to playful animal encounters and a whimsical museum, this captivating road trip promises to create unforgettable memories for everyone in your group
    • Kid-Friendly
    Can depart from: Chicago Area, Milwaukee Area
  • PERFECT FOR MOVIE BUFFS
    Cinema & Scenery

    Cinema & Scenery

    $39 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
    Can depart from: Chicago Area, Milwaukee Area