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Milwaukee

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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  • CAN BE DONE IN WINTER
    A Riverside Ramble

    A Riverside Ramble

    $65 CAD
    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

    $65 CAD
    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
  • STAFF PICK
    Cinema & Scenery

    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
Three women walking through tulip fields
Winding roads through mountains at sunrise

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