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 ...
Wine Time and Hidden Gems
From $39
Craving rolling vineyard views, artful little towns, farm markets and that breezy, laid-back feel only lakeside moments can deliver? This is the trip for you! It’s the kind of place that deserves more than a quick visit...make it a weekend if you can!
When to Go
Thurs - Sun, Spring - Fall
ends near
Picton, ON
- Free Shipping on Orders $100+
- 30-Day Returns & Exchanges
- No Booking Required
essentials for your trip
Detour Diaries: Ontario
Packed with 500+ of our favourite road trip stops across Ontario, Detour Diaries features 130+...
Lilac Road Trip Journal
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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.
Wine Time and Hidden Gems
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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"The most fun, stress-free way to explore Ontario”
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“Trust me, you need to try this”
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“I still can’t get over how fun it was”
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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.
