All Things Charming
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All Things Charming

All Things Charming

$65.00 USD
Sale Sold out

One trip is required per group.

* "PDF Instant Download" means the trip will be sent by email as a PDF document, and not by mail (the email is sent immediately after completing your purchase)

WHAT TO EXPECT

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!

Trip Highlights

  • A boardwalk with hidden history
  • The cutest small town
  • Epic photo ops
  • Meet some furry friends!
  • Picture perfect lakeside views

AVAILABLE TO DEPART

Available to depart Thursday - Sunday throughout the year.

SUGGESTED FOR

  • Romantic getaways
  • Families with older kids
  • History buffs
  • Budding photographers
All Things Charming
All Things Charming
All Things Charming
All Things Charming
All Things Charming

Itinerary

STOP 1

Before enjoying a historic park and boardwalk trail, snap a photo at a famous filming location! Drive time to the second stop is 20 minutes.

STOP 2

Grab a coffee and visit a truly quirky museum that will bring out the kid in you. Drive time to the third stop is 20 minutes.

STOP 3

Scenic lake views, tiered gardens, picturesque photo ops and so much more awaits at your next stop. If you're ready for lunch, we've recommended a fantastic brewery! Drive time to the fourth stop is 15 minutes.

STOP 4

A farm with a cause and the cutest alpacas, horses, goats and more? This spot is the perfect way to end your day!

Region

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Can depart from

Chicago Area, Milwaukee Area

Before you go

What You'll Need to Bring

  • Camera
  • Road Trip Snacks
  • Walking Shoes
  • Water
  • Cash
  • Sunscreen (lots of easy outdoor activities)
  • Bug Spray
  • Respectful attire is required for one stop
  • Reusable Shopping Bags

Additional Details

  • Kid-Friendly

FREQUENTLY ASKED QUESTIONS

We're here to help!

Please see the approximate driving distances below. Please note this just includes round-trip driving distances and not time spent at stops.

From Chicago, IL:

2 hours and 35 minutes / 87 miles

From Milwaukee, WI:

3 hours and 10 minutes / 154 miles

From Rockford, IL:

3 hours and 55 minutes / 196 miles

*We recommend booking an overnight hotel if the driving distance is greater than 4 hours round-trip.

This trip is best done Thursday - Sunday, any season throughout the year.

We do not recommend traveling between Monday - Wednesday, or on holidays.

We recommend departing between 9:00 - 9:30 am if you’re coming from Chicago. The later you leave, the less time you’ll have to explore all of the stops.

Unfortunately, this trip is not dog friendly. We recommend leaving your furry friends at home for the day.

We recommend bringing between 2- 5 people on your surprise road trip adventure.

First Stop: No fee

Second Stop: Our featured stop requires a $6 admission fee per person. We’ve provided several free alternatives.

Third Stop: No fee

Fourth Stop: Our featured stop requires a $5 admission fee per person. We’ve provided a free alternative.

*Please note: gas, tolls, and food are additional costs at your own expense.

After booking your trip, we'll send you a confirmation email with a few recommended accommodation options.

Customer Reviews

Based on 2 reviews
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Sarah Krieger
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I would not recommend this trip
Excellent! I would definitely recommend this trip
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My First Guess Where Trip

Loved the places! Truely charming as described! I lived not far from these places for 7 years and didn't know about these things nearly in my own back yard. :)

C
Christy Reyes
Overall, how would you rate this trip?:
I would not recommend this trip
Excellent! I would definitely recommend this trip
Rate how active the trip was:
Not very active
Very active
Rate how accessible the trip was:
Not very accessible
Very accessible
Rate how 'unique' the stops were:
Not really
Yes, very unique!
Fun day!

We were very excited to go on our day date full of surprises and we were not disappointed. The only thing I would change is the time of year we went. We missed the fall colors but that is on us not Guess Where trips. This was such a great day and we went places we never knew existed and we made lots of friends and wonderful fun memories. I have many pictures but I only shared the ones that wouldn't spoil the surprise. Will definitely do this again!

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