Woman holding four Guess Where Trips envelopes while on road trip

Milwaukee

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

  • Gift Card [Digital $USD]

    Gift Card [Digital $USD]

    $65.00 USD
    Instantly send the gift of a one-day surprise road trip! Digital gift cards can be sent immediately or scheduled to be sent on a specific day.
  • CAN BE DONE IN WINTER
    A Riverside Ramble

    A Riverside Ramble

    $65 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

    $65 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
  • STAFF PICK
    Cinema & Scenery

    Cinema & Scenery

    $65 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
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!