Vistas & Caves

4.6 (74 reviews)

From $39

This road trip is a quick jaunt north of Toronto and is ideal for outdoor enthusiasts. It really is the perfect mix of everything

When to Go Weds - Sat
ends near Orangeville, ON

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  • Free Shipping on Orders $100+
  • 30-Day Returns & Exchanges
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essentials for your trip

Detour Diaries: Ontario

Detour Diaries: Ontario

Packed with 500+ of our favourite road trip stops across Ontario, Detour Diaries features 130+...

Lilac Road Trip Journal

Lilac Road Trip Journal

Track all your local adventures - big or small!

Trip Highlights

  • Road trip worthy bakeries and shops
  • Historic attractions
  • A variety of trails and natural attractions
  • Adorable hamlets and scenic driving routes
  • Multiple recommendations included on every stop

How Long Is This Trip?

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

  • From Toronto: 3 hours and 8 minutes / 230 km
  • From Oakville: 2 hours and 52 minutes / 206 km
  • From Hamilton: 3 hours and 23 minutes / 260 km
  • From Pickering: 3 hours and 28 minutes / 277 km
  • From Kitchener: 3 hours and 18 minutes / 210 km
  • From Barrie: 3 hours 12 minutes / 218 km
  • From London: 5 hours 14 minutes / 410 km
  • From Collingwood: 2 hours 44 minutes / 187 km

When Can I Go?

Days of the week: Wednesday through Saturday

Seasons: Year-round

Not recommended: Sunday - Tuesday, Holidays

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.

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Vistas & Caves

4.6 Physical Package

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.

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Road Tested by Our Team

Our team spends 40+ hours researching, driving, and vetting every route: talking to locals, discovering hidden gems, and making sure every stop is worth your day.

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.