Aerial view of Toronto cityscape during sunset, showcasing various buildings and the CN Tower.
Toronto Gems
Toronto Gems
Toronto Gems
Toronto Gems
Toronto Gems

Toronto Gems

4.4 (10 reviews)

$39

Explore all of Toronto's downtown gems in a completely new way - ditch the car and walk or bike while you explore! This trip is best for anyone who isn't super familiar with the Toronto core, plus there's an optional “scavenger hunt" so there is something for you to find and decode at each stop!

When to Go Tues - Sat
ends near Distillery District, Toronto

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Trip Highlights

  • Epic eateries
  • Historical information with a few spooky stories
  • Photo-worthy stops
  • Play eye-spy throughout this trip!
  • Multiple recommendations included on every stop

How Long Is This Trip?

This trip is a little bit different, as we recommend walking between stops! You will be heading into downtown Toronto, and the total distance from the first to the last stop is 35 min (2.8km).

If you’re taking the train into Union Station, it is a 10 minute walk to the first stop and 25 minutes back from the last. If you drive, this will depend on where you choose to park. The website linked here will give you a good idea of where lots are, however you’ll be able to find street parking around too

When Can I Go?

Days of the week: Any day, with some closures on Mondays

Seasons: Best done Spring through Fall

Not recommended: 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.

Read our full return policy →

Toronto Gems

4.4 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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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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