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What to expect

From Southern Ontario/GTA: Stay in your own lakeside cottage with a stylish mid-century vibe and well-equipped kitchen. Guests also have full access to the outdoor deck, BBQ, fire pit (firewood is supplied), 2 kayaks and snowshoes for those getaways. Please avoid this getaway if you've taken our 'Weird and Wonderful' trip.

Trip Highlights

Two nights of pre-booked accommodation

7 envelopes of surprises set over 3 days

Two dinner reservation options (dinner not included)

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

Mountain top hikes

Lakeside adventures

Tons of Instagrammable opportunities

Suggested for
  • Photographers
  • Small group of friends
  • Girlfriend Getaways
  • Small Families
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.  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 is anytime after 3 pm. After checking in, you’ll want to soak up all the vibes and hang around a bit before dinner. Have a drink by the water, walk down to the lake or hang in your room.

Stop 3

In the pre-trip survey, we’ll ask what type of meals you’re interested in eating. There are a few restaurants 20-30 minutes away. Alternatively, we can provide nearby grocery stores as this getaway is equipped with a kitchen.

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: lakes, an adorable village, excellent hiking trails, breweries and more. We’ll even provide a list of lunch recommendations based on your dining preferences.


Stop 5

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

An ice pack and cooler
Bathing Suit
Beach towel
Bug Spray
Hiking Shoes
Ice Skates (Optional)
Outdoor Gear
Reusable shopping bags
Road Trip Snacks
Walking shoes
Additional Details
2 Kayaks
Full Kitchen
Indoor/Outdoor Fireplace
Somewhat accessible

Frequently Asked Questions

We're here to help!

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

You’ll be staying at a stylish mid-century styled 2 bedroom/1 bath cottage with a  well-equipped kitchen. A propane furnace, wood stove, TV is available in the den. Outside, enjoy the waterside dock, firepit or head out for a kayak.

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.

We do not allow pets on our getaways, 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 or four guests (each date is different.) 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 43 minutes / 273km
  • From St Catharines: 3 hours and 31 minutes / 354km
  • From Kitchener: 3 hours and 11 minutes / 327km
  • From London: 3 hours and 58 minutes / 414km
  • From Barrie: 1 hour and 35 minutes / 162km
  • From Kingston: 4 hours and 22 minutes / 425km
  • From Ottawa: 4 hours and 22 minutes / 379km