Wine Time and Hidden Gems
Home / Trips / Wine Time and Hidden Gems

Wine Time and Hidden Gems

Wine Time and Hidden Gems

Regular price $49 USD
Regular price USD Sale price $49
Sale Sold out

One package is recommended for 1-5 people.

* PDF Instant Download will be emailed immediately after purchasing and is the entire trip in one PDF document.


This trip requires a little more driving, but we promise it's worth it. We've found quite a few hidden quirks and gems along the route which we know you'll love. We've packed the last stop full of great recommendations in case you want to make this day trip into an overnighter.

Trip Highlights

  • An iconic market
  • Some quirky & cute wineries
  • Fantastic local restaurant recommendations
  • Drive by an old ‘Ghost Town’
  • Recommended hikes along the way
  • A lighthouse and beach photo opp


Available to depart any day with limited hours on Monday-Wednesdays.


  • Those looking for longer day trips or an overnight getaway
  • Foodies
  • Girlfriend Getaways
  • Couples
  • Photographers



The first stop is the perfect place to start your day. The drive time to the second stop is 20 minutes.


The second stop allows you to connect with a bit of nature. Not a fan of hiking? There's a few photographic opportunities here you don't want to miss. The drive time to the third stop is 30 minutes. Travel Tip: We've recommended an extra hike that requires a reservation. If you want to book this spot, please send us an email for the provincial park name.


Welcome to the 'wine-ding' road. You'll have a lot of fun at this stop. The drive time to the third stop is anywhere between 5-30 minutes (depending on where you want to go).


We've packed SO much stuff into the fourth stop. The choice is up to you!



Can depart from

Toronto Area, Kingston Area

Before you go

What You'll Need to Bring

  • Camera
  • Cash
  • Money
  • Outdoor Gear
  • Reusable Shopping Bags
  • Road Trip Snacks
  • Walking Shoes
  • Water


We're here to help!

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

• From Toronto: 4 hours and 15 minutes / 399 km

• From Oakville: 4 hours and 43 minutes / 471 km

• From Hamilton: 5 hours and 20 minutes / 533 km

• From Pickering: 3 hours and 22 minutes/ 323 km

• From Kitchener: 5 hours and 53 minutes / 582 km

• From Barrie: 5 hours and 31 minutes / 558 km

This trip can be used all year. There are some closures Monday-Wednesday, however we’ve recommended alternative stops. Please keep in mind that there might be closures on holidays.

We recommend leaving anytime between 8 am-9 am.

Only the alternative hike suggestion on the second stop requires an entrance fee and a reservation. It is $21/vehicle, so please email us if you would like the park name to book in advance. All other stops are free!

You can bring your pup on Wine Time and Hidden Gems!

The trip includes patio options for when it’s warm & take out options. There will also be at least one dog-friendly activity at each stop. If you bring your furry friend, you will be unable to bring them into any indoor suggestions.

We recommended bringing up to 5 people on your surprise road trip. If you're bringing a larger group, we highly recommend having one person in charge of booking reservations at the restaurants and attractions in advance. In your confirmation email, you'll receive a copy of the itinerary.

We have included a few accommodation recommendations in the confirmation email.

Customer Reviews

Based on 2 reviews
Overall, how would you rate this trip?:
Rate how active the trip was::
Rate how accessible the trip was::
Rate how 'unique' the stops were::
Make this into an overnight trip!

Fantastic trip to one of my favourite areas in Ontario. Highly highly highly recommend booking an overnight hotel at last stop. Book as early as you can as the hotels fill up. Would be great for a girlfriend getaway trip or bachlorette. If you're doing it as a day trip from Toronto leave early!

Sydney Bates-Schouten
Overall, how would you rate this trip?:
Rate how active the trip was::
Rate how accessible the trip was::
Rate how 'unique' the stops were::
An Epic Weekend Getaway

All I can say is WOW! I had been to this area quite a few times before but Guess Where Trips introduced me to so many new hidden gems. Don't even get me started on that taco place on the fourth stop. One of the best meals I've ever had!