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What to expect

From Southern Ontario/GTA: Spend your getaway next to a river (with a private hot tub) just 5 minutes from a historic town. Your accommodation is set on 7 acres and your unit is just one of four, making the stay incredibly private. We've included 7 surprise stops over 3 days that include quaint cafes, picturesque viewpoints, funky museums and a couple of dinner reservations. Please avoid this getaway if you've taken our 'Local Markets & Picturesque Town trip.

Trip Highlights

Two nights of pre-booked accommodation

7 envelopes of surprises set over 3 days

Two dinner reservations (dinner not included)

A historic town with great local markets and restaurants

Beautiful gorges, riverside walks and a small waterfall

A mini self-guided surprise route in the country

Suggested for
  • Couples
  • Photographers
  • Foodies
  • Seniors
  • Not Pet-Friendly
  • Not Kid-Friendly
Available to depart
See dates in drop down 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.  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.

Stop 2

Check-in starts at 3 pm. We guarantee you’ll fall in love with the uniqueness and charm of this private riverside boutique stay. Your hosts are on-site to assist with any check-in needs. A few surprises are included once you settle into your room.

Stop 3

We have a few dinner options for you to choose from and can make reservations at your request anytime between 5pm-8pm. Based on your pre-trip survey, we’ll select a restaurant that best suits your dining interests. Rather eat in? We can provide you options for take-out or delivery.


Stop 4

A few breakfast essentials are included in your stay to get you started for the day. If you’d prefer to dine out, we’ve provided a few different breakfast and cafe options.

Stop 5

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: local markets, historic villages, riverside hikes and picturesque museums. We’ll even provide a list of lunch recommendations based on your dining preferences.

Stop 6

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

Stop 7

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
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Before you go

What You'll Need to Bring

Additional Details
5 minutes from town
Hot tub
Queen bed
River view
Small kitchen
Somewhat accessible

Frequently Asked Questions

We're here to help!

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

Your private riverside unit includes a private hot tub, AC, small kitchenette (with fridge, toaster, microwave and coffee maker). Some added touches are the flat screen TV and pair of robes. The unit is narrow, measuring at 26 m², as it is a recently refurbished shipping container. 

The property is set on 7+ acres, featuring only 4 individual accommodation units, with all units being on the ground floor

“Amazing. Peaceful. Immaculately clean. The most beautiful view of the river and gardens. The hot tub was the nicest touch for a relaxing getaway. We loved walking down to the river to sit in the gazebo or taking the 5-minute drive into town.”-a recent review

This getaway package includes two nights at one of our favourite accommodations in Ontario, dinner reservations for Friday and Saturday, 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 20% 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 requires a minimal fee to enter.

After booking, we’ll send you a link to a pre-trip survey that needs to be filled out. On the survey, we 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 10am on the first day.

The selected accommodation provider does not allow pets or children. Please contact us at if you’d like other kid or pet-friendly day trip recommendations.

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 our  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. The maximum guests you can book per stay is 8 guests. 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: 1 hour and 25 minutes / 116km
  • From St Catharines: 1 hour and 48 minutes / 128km
  • From Kitchener: 27 minutes / 25km
  • From London: 1 hour and 31 minutes / 131km
  • From Windsor: 3 hours and 16 minutes / 308km
  • From Barrie: 1 hour and 46 minutes / 134km
  • From Kingston: 4 hours and 6 minutes / 358km