Guess where you’ll go.

Credit: Keith Tanner –

After a challenging year and a half, travel is definitely something that has been on all of our minds lately! If you’ve been itching to get away, Guess Where Trips is a must-try adventure that offers you the experience of a lifetime. Guess Where Trips takes travelling to a whole new level as a brand that specializes in one-day, curated, surprise road trips in Toronto, Vancouver, Ottawa, London (ON), and Windsor.  

Guess Where Trips was created by Jessica Off after several years of planning travel. The idea initially began as a Christmas gift for Jessica’s parents, but she loved planning their trip so much she decided to make a business out of it and, thus, Guess Where Trips was born. The team at Guess Where Trips fully understands how long it takes for the average trip to be planned and booked, and one of their greatest joys is creating exciting itineraries that allow travellers to discover new places they would have never seen before.

Credit: Keith Tanner –

What’s great about Guess Where Trips is that the team does all the planning for you by curating a unique trip designed to fit anyone’s travel needs and style. From winery tours to Instagrammable locations to hiking, shopping, cultural/historical trips, waterfalls, and historical haunts, the possibilities are endless! When booking on the site, you can also decide how long or short your day trip will be and how many stops you want to input along the way. Guess Where Trips will also add in restaurant and activity recommendations during your trip based on your travel style. 

Credit: Keith Tanner –

Here’s how it works:

Firstly, select your trip style – are you looking for an indoor or outdoor-based trip? Do you want hidden gems or Instagrammable attractions along the way?

There’s even a before-you-go guide that will help guide you on what to pack even before knowing the surprise destination. 

In your package, you will also receive several envelopes that will lead you to several surprise destinations on your trip.

The morning of, you open up your first envelope and your adventure begins! 

*Note that transportation, gas, entrances (majority of stops are free), parking fees, food, beverages and gratuities are not included in Guess Where Trips.

Credit: Keith Tanner –

This is the perfect experience for families, friends, couples, or individuals looking for a fun way to travel this year. Most Guess Where Trips are scheduled to last between 6-8 hours, which also includes the driving and time spent at each stop. It is also important to note that you can bring as many people on the trip that will come, as the price is per trip and not per person (however, it is recommended to have 2-5 people per trip). Additionally, most of the activities and attractions recommended by Guess Where Trips are free or have a minimal entrance cost (under $10/per person)., and almost all trips are kid-friendly and dog-friendly!

So what are you waiting for?! Check out for more information and to book your surprise trip today!

Published by HOLR Magazine.