Going on a Surprise Road Trip with Guess Where Trips

Planning trips is something that I LOVE. Picking out the perfect places to dine, the best sites to see, and the most unique attractions makes me so happy. I find that I thrive off the challenge to find adventures that are a little out of the box, but more than anything, I like having the control of knowing that everywhere I visit will be 100% accessible. There’s nothing worse than leaving the planning up to someone else, just to find out that they didn’t do the proper research and I can’t participate after all. 

That’s why going on going on a surprise Road Trip with Guess Where Trips was both incredible and terrifying at the same time. For one day, I put all my control behind and went on an accessible Road Trip of a lifetime. No planning, no strict schedule, and no colour coded itinerary — just me, my sister, my vehicle, and a couple of envelopes telling us where to go next. 

It was seriously the day-trip of a lifetime!  

What is Guess Where Trips?

Guess Where Trips is an incredible Canadian company that offers surprise single day road trips in the Toronto, Ottawa, and Vancouver areas. They have a wide range of trip themes you can choose from depending on your travel style and preferences, including trips centered around:

• • • Outdoor Adventures 
    • Wineries and Restaurants 
    • Local Markets & Picturesque Towns 
    • Haunted Attractions
    • Festive / Seasonal Activities

Although you get to choose the theme of your trip, you won’t actually know where you’re going until you depart, which is what makes it so exciting! 

How Does Guess Where Trips Work?

The first step is to head to Guess Where Trip’s website and choose your adventure. In addition to choosing one of their specially curated trips, you can also opt for them to send you a surprise trip or have them customize a trip just for you. This would be a perfect option for a special occasion, or if you have accessibility requirements that are not included in their other packages. 

After you finish picking a trip on their website, you will be mailed a beautiful package with a series of envelopes. In one envelope you will find a ‘Before You Go’ guide with a packing list, approximate driving distances and more tips to plan for your day ahead. 

 

The next 4-5 envelopes will make up your day’s itinerary — I suggest opening them as you progress through your stops (rather than all at the beginning) in order to keep the thrill alive for the whole day. In most cases, each envelope will include small roadside stops to break up your driving time, as well as alternative stops if you don’t like the stop they have planned or simply just want to add onto your day! Guess Where Trips does an outstanding job at planning your route and including quirky / rare spots that you’re likely to have never visited before. 

 

According to the Guess Where Trips website, most trips are between 7-10 hours, which includes the driving and time spent at each stop. If you would like to make it an overnight trip, you can let them know when you purchase your package, and they will include a list of recommended accommodations in the general area of your last stop. Although the trips are designed to be completed in one day, the itinerary they have planned for you will certainly be jam-packed, so I do recommend staying overnight if you want to complete the trip in a more slow paced manner. 

Is the Itinerary Wheelchair Accessible?

Yes, many of their trips are wheelchair accessible! Guess Where Trips indicates directly on their website whether the trips are wheelchair accessible or not, so you know before you book.

Personally, I was very thrilled to see this on their website, as so many travel companies are not transparent or forthcoming about accessibility measures in the slightest. Normally I have to call or email a bunch of people to simply ask if I’ll be able to participate, but with Guess Where Trips, it was all laid out right there for me. It definitely made me happy knowing that accessibility is on their radar when planning trips and that they make it so easy for people with disabilities to book and experience these adventures, just like anyone else. 

It is also worth noting that Guess Where Trips has incredible customer service. If you are worried about whether or not a trip will meet your needs, simply reach out to them with your access needs, and they will be happy to match you with a trip that works for you. If there are no trips that meet your needs, they can always put together a custom itinerary that matches both your accessibility requirements and personal preferences! 

My Trip

My day trip was honestly so much fun. It included a mix of fun little ‘instagrammable’ spots, delicious food and wine, a ‘choose your own adventure’ full of hiking spots & attractions, and an adorable little town that I’ve always wanted to visit. I don’t want to say too much because the surprise of the trip is what makes it so exciting, but here are a few photos to show what kinds of things we got up to! 

Snapshots from the day

Overall, it was so much fun to get away for the day and explore new places I never would have come across otherwise. For the most part, the stops they planned weren’t major tourist attractions, but rather, smaller local spots that I had never heard of before. This made it so much different than anything I would have been able to plan on my own. 

It is also worth noting that all the stops were 100% COVID friendly. Most of the stops were outdoor (or had mostly outdoor elements), but even the ones that required us to go inside were following all social distancing protocols, making us feel very safe and comfortable. 

Guess Where Trips also continually updates their website with the restriction status of each stop, so you will be able to verify ahead of time that each of your stops is open. Please just be mindful that you will likely be entering different zones on your trip; as such, if you live in a red zone, please be respectful of the local community and delay your trip to a later date. Unless you purchased a seasonal package (i.e. on of their Christmas themed adventures), your Guess Where Trips itinerary can be used at any time. You will not be out money if you choose to go on the trip later than you intended. 

With all that being said, Guess Where Trips is a phenomenal gift for any travel-lover in your life this holiday season! Whether used as a family outing, a couples retreat, or a solo adventure, GWT will certainly help scratch that travel itch I know where all feeling right now.