Water reflecting forest and blue sky.
Lake reflecting blue sky and fluffy clounds
Woman packing up baked goods into a paper bag.
Woman with red hair standing in front of a dark forest.
Hiker with orange backpack walking along a forest trail.
Two people clinking wine glasses in front of a wall mural.

Muskoka Meandering

4.6 (63 reviews)

From $39

Muskoka Meandering is the perfect way to escape from the hustle and bustle of the city and immerse yourself in nature while enjoying delicious wines and beers, beautiful scenery and lookouts, and charming small towns.

When to Go Weds - Sat, mid-May - mid-October
ends near Port Carling, ON

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  • Free Shipping on Orders $100+
  • 30-Day Returns & Exchanges
  • No Booking Required

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+...

$59
Lilac Road Trip Journal

Lilac Road Trip Journal

Track all your local adventures - big or small!

$25

Trip Highlights

  • Explore a cute town with a unique connection to the past
  • Scenic trails, boardwalks and lookouts
  • A dockside cafe to dip your toes in the water
  • Local winery and brewery options
  • A sunset beach spot to end the day
  • Multiple recommendations included on every stop

How Long Is This Trip?

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

  • From Collingwood: 3 hours and 43 minutes / 288 km
  • From Barrie: 2 hours and 36 minutes / 219 km
  • From Peterborough: 4 hours and 7 minutes / 313 km
  • From Downtown Toronto: 4 hours and 45 minutes / 438 km
  • From Oakville: 4 hours and 43 minutes / 446 km
  • From Oshawa: 4 hours and 37 minutes / 334 km

When Can I Go?

Days of the week: Wednesday through Saturday

Seasons: Mid-May to mid-October

Not recommended: Holidays, Sundays - Tuesdays, Mid-Ocober through mid-May

Travel Tips

You can travel in the winter months; however, many seasonal options will be closed and some trails/lookouts are not maintained or plowed so they may be more difficult to access.

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.

Read our full return policy →

Muskoka Meandering

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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Frequently Asked Questions

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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.

Donna S. 🇨🇦

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.

Mary Y. 🇨🇦

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!

Megan M. 🇨🇦

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.

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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.