Which Way? A Surprise Road Trip Card Game
Go on your own mini surprise trip with Which Way. Simply pick a card to reveal your next ...
All Things Charming
From $39
Just outside Chicago, this thoughtfully planned road trip takes you from lakeside scenery and charming small towns to playful animal encounters and a unique museum experience. With a mix of relaxing and lighthearted stops, it’s an easy and memorable way to explore something a little different at your own pace.
When to Go
Thurs - Sun
ends near
Libertyville, IL
- Free Shipping on Orders $100+
- 30-Day Returns & Exchanges
- No Booking Required
essentials for your trip
Mint Road Trip Journal
Track all your local adventures - big or small - in one place. With space...
Road Trip Tote Bag
An essential tote bag for your road trip ahead. Carry everything from your surprise package...
Trip Highlights
How Long Is This Trip?
When Can I Go?
Shipping & Returns
Shipping: Free shipping on orders over $100. Standard shipping takes 4–10 business days. Need it faster? Choose the fastest option at checkout for 2–4 business day delivery.
Returns: Not the right fit? Reach out within 30 days of purchase to start a return. Products just need to be unopened, unused, and in their original packaging, return shipping is your responsibility. Digital trips, gift cards, and opened products can't be returned.
Exchanges: Want a different trip instead? Email us at questions@guesswheretrips.com within 30 days of your order, there's a small $8 reshipping fee to send your new pick out. Digital trips cannot be exchanged.
All Things Charming
Here's How It Works
Browse by location and find a surprise trip that fits your day. Every route is road-tested by our team.
Your surprise destinations stay sealed until you're ready for them. One envelope at a time on the road, all day long.
Hidden gems, local favorites, and stories you won't find on Google. That's what's waiting for you.
What People Love About Our Trips
Rated 4.9/5.0 stars
What an Amazing Day!
Our daughter gave us this for Christmas and we finally pulled it out this week, July now. We love a road trip and loved the mystery of each new step. Great things to see and experience. Great restaurants to enjoy. I’ve recommended it to all my friends. Amazing.
First Time…There WILL be a second!
Knowing the area we went I was very pleasantly surprised. We saw things I did NOT know existed! One of the stops was closed however we were able to walk up to it for a photo.
Great day away!
Did this trip with my mom for Mother’s Day. Lots of quaint little stops and places to explore! They also gave a few options at each stop so you could choose your own adventure! Will definitely be doing this again, had a wonderful time!
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“Guess Where Trips thinks of everything”
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We Remember Experiences, Not Things.
Research consistently shows that spending time together creates more lasting happiness than buying more stuff. Every Guess Where Trip is thoughtfully planned to help you reconnect, explore, and create memories that last long after the day is over.
