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What to expect

From Southern Ontario/GTA: Stay in a boho-chic, vintage-inspired boutique motel in the heart of a trendy village. We've included 7 surprise stops over 3 days that include the best restaurants, breweries, waterside adventures and a few waterfalls. Please avoid this getaway if you've taken our 'Markets to Mountains' or 'Waterfall Route' trip.

Trip Highlights

Two nights of pre-booked accommodation

7 envelopes of surprises set over 3 days

Two dinner reservation (dinner not included)

Up-and-coming breweries and cideries (other options available)

Spa options available (at an additional cost)

Lakeside adventures

A few waterfall hikes (other options available)

Tons of Instagrammable opportunities

Suggested for
  • Couples
  • Photographers
  • Small group of friends
  • Girlfriend Getaways
Available to depart
See dates in link OR request a date 2 months out with a $100 deposit.


Stop 1

Depending on what time you request to leave, we’ll include one or two surprise stops before checking in. Stops on your first day could range from funky markets, hikes through caves, cute towns, or a country cidery.  During the booking process, we’ll ask what time you’re able to hit the road on day one. This will allow us to choose how many stops you’re able to complete before checking in.

Check our FAQ below, for round-trip driving distances to the selected accommodation.

Stop 2

Check-in is anytime after 4 pm. After checking in, you’ll want to soak up all the vibes and hang around a bit before dinner. Play some bocce ball, eat a few oysters or sit by the fire.

Stop 3

In the pre-trip survey, we’ll ask what type of restaurants you’re interested in, and reserve a spot for both nights. There are quite a few to choose from in the area.

Stop 4

For the second day of your getaway, we’ve provided you with a variety of options that will keep you busy. Your pre-trip survey will help us customize the types of activities we’ll include here. Feel free to do as many or as few of the recommendations we suggest.

This area offers a little bit of everything: beaches, an adorable village, waterfalls, shopping, cideries, breweries and a ton of hikes. We’ll even provide a list of lunch recommendations based on your dining preferences.


Stop 5

Ready for dinner? We’ll have dinner reservations ready for you at a pre-set time determined by you. I

Stop 6

Check-out is at 11 am the next day. We’ve included a few roadside surprise stops for your trip back home. When filling out your pre-trip survey, you’ll provide us with a set time you’ll need to be home for.

Estimated Travel Time
to First Stop


Calculate distance to the first stop

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Before you go

What You'll Need to Bring

An ice pack and cooler
Bug Spray
Hiking Shoes
Outdoor Gear
Reusable shopping bags
Road Trip Snacks
Snowshoes (Optional)
Additional Details
In town
Outdoor Firepit
Restaurant onsite
Somewhat accessible

Frequently Asked Questions

We're here to help!

We don’t want to ruin the surprise, but have included a few hints:

This recently-renovated boutique motel offers an immaculately designed room, with some pretty funky amenities: courtyard, bocce ball, s’mores by the fire etc. All the little details of this ‘retro motel’ are so incredibly aesthetically pleasing.

The onsite restaurant offers:

-Coffee services (from 8am-11am)

-Lunch (Wednesday-Saturday) 11am-4pm

-Dinner (Friday & Saturday, 4pm-9pm)

-Brunch (Saturdays & Sundays 8am-12pm)

This getaway package includes two nights at one of our favourite accommodations in Ontario, dinner options for bott nights, 7 surprise envelopes that include pre-planned and customized activities. The package comes in a pretty box that is mailed (via Xpresspost) 2 weeks prior to your departure.

The price also includes a service fee that Guess Where Trips adds onto the cost of the accommodation. This helps pay for our time planning your road trip, printing, material costs, handling and shipping your trip.

Most of the activities included in each surprise stop are free or require a minimal fee to enter.

When booking, we’ll ask what time you would like to depart and we’ll plan your first day around this. To make the most of your experience, we recommend departing around 10 am on the first day.

The selected accommodation provider is not pet friendly but is kid friendly.

Please select the last option ‘request-a-date’, where we require a $100 deposit. Please select three dates at least 2 months out to ensure we have availability. The accommodation providers we work with have very few rooms and have to be booked months in advance.

If we cannot find any dates that work with your schedule, we can refund your $100 deposit.

If you have more questions, we’d be happy to assist. If you’d like to set a time for us to call, please email us with your contact number and the best time to call. You can email us at 

Unfortunately, our getaways are only 2 nights. For shorter trips, we recommend  one-day surprise trips and we provide overnight recommendations via email after you book.

For this getaway, there’s a maximum of two guests per unit for the king room, and four guests per unit for the double queen room. For large group requests, please provide us with a minimum of 4 months in advance for groups this size. For smaller groups (4-6), please provide us with a minimum of 3 months in advance.

As soon as we receive your order, we start working on the customization of your trip. Many of the accommodations we work with also have a strict cancellation policy. Because of this, we do not allow cancellations after a booking has been made.

Unfortunately, no coupons or ‘road trip gift cards’ can be applied to getaways.

However, we do have getaway-specific gift cards that can be applied. Please email us beforehand for us to discount this off your stay.

Approximate driving distances are listed below – this is how long it would take to drive to the accommodation (one way) and does not include time spent at stops along the way.

  • From Toronto: 2 hours and 11 minutes / 171km
  • From St Catharines: 2 hours and 52 minutes / 240km
  • From Kitchener: 2 hours / 147km
  • From London: 2 hours and 58 minutes / 224km
  • From Windsor: 4 hours and 44 minutes / 432km
  • From Barrie: 1 hour and 12 minutes / 75km
  • From Kingston: 4 hours and 21 minutes / 417km