I’m a big fan of day trips. There’s just something about hitting the open road and visiting a different place for a day. Luckily, Ontario has so many great options – whether it’s visiting a quaint little town, exploring hiking trails or going to a historical site – the choice is endless. But maybe there is too much choice. That’s where Guess Where Trips comes in. An Ontario company that is redefining road trips. They create exciting surprise itineraries that take you to new places you’ve never been before. (Updated April 2022)
How does Guess Where Trips work
1. Choose Your Day Trip
From the Guess Where Trip website, the first step is to select a one day road trip based on your interests and preferences. This can include driving time from your starting location to attractions that appeal to you, like history/culture, beaches, cute towns, and hiking to name a few. You also have the option to filter by accessibility, whether that’s wheelchair, vegan, family-oriented, or dog-friendly. Or, if you really want to leave it up to Guess Where Trips, take the road trip quiz to see what suggested trips are best for you.
Each surprise road trip includes a curated itinerary that you’ll never really know exactly where you’re going until the day. In Ontario, trips are focused in southwestern Ontario (Windsor to London), central Ontario (Toronto), and eastern Ontario (Ottawa). The best part is all the research and planning are all done for you. Guess Where Trips plan one day surprise road trips for only C$65.
Guess Where Trips Locations
Guess Where Trips are found in the following locations:
- Ontario trips include Greater Toronto Area, London, Windsor and Ottawa
- Alberta trips include Calgary and Edmonton
- British Columbia trips include the Vancouver area
- Nova Scotia trips include the Halifax area
Best Selling Guess Where Trips
|Local Markets and Picturesque Towns||Takes you to a historic village, a riverside trail and gorge|
|Funky Florals and Fine Wines||Must love wine, food and flowers|
|Weird and Wonderful Things||Takes you to a secluded waterfall and unusual attractions|
|The Small Town Charm Trail||Brings you to quaint small towns full of charm|
|Outdoor Adventures & Scenic Roads||Takes you to cool attractions, good food and scenic roads|
|Bridges to Beaches||Off the beaten path to sandy beaches and picturesque bridges|
2. Get your Package
Now that you have chosen your trip all you have to do is wait for your surprise package to arrive in the mail (shipping is included). You do have the option for express shipping (an additional cost) or virtual delivery (it’s just not as fun). There’s really no better feeling than opening the mailbox to find your package has arrived!
In your package you will receive 5 envelopes – a ‘Before You Go’ plus four secret itinerary stops. Only open the ‘Before You Go’ envelope, at least the night before. The guide shares everything you need to know while still keeping the details of your day a secret. What you’ll find out is…
- what time you should depart (strongly recommend you depart by the suggested time to be able to take advantage of the full itinerary)
- a glimpse into your four surprise stops each with driving time and recommended duration
- what to wear, pack and bring with you
- how long the round-trip will take (time/km)
- frequently asked questions specific to your day trip
3. Pack your Bags
Your bag is packed, and you’re ready to jump in the car and hit the open road, but before you do, open the ‘Your First Stop’ envelope. It holds all the information about your destination, plus interesting facts and history. Each of the four secret stops will have recommended options for additional side trips or mini-stops, try and explore as many as you can.
Add the first destination into your GPS, and don’t forget every road trip needs some good tunes. Guess Where Trips has even supplied you with a road trip playlist on Spotify. Ok, now you’re ready – let’s go!
Your Guess Where Trips Adventure Awaits You
Every curated surprise itinerary will bring you to four destination areas. Each of the four stops is packed with information, travel tips, and maybe even some exclusive Guess Where Trips coupon codes for some of the select local businesses.
There will also be recommended roadside attractions and mini-side trips between stops. Your day will be brimming with activities that suit a wide variety of interests. Even though your day has been meticulously planned, there’s still a great feeling of it being carefree and spontaneous. It’s the element of surprise!
My Guess Where Trips Review
Here’s my personal review.
My Surprise Day Trip
You won’t read about any Guess Where Trips spoilers here. As much as I am eager to share the details of my amazing day trip, I hate to ruin the surprise for you. All I will say is that my surprise trip is called ‘Secrets in the South.’ It included a scenic drive in the country to do some hiking, stopping by a lovely village that I’ve long had on my list to visit, going to a town with some historical attractions, and of course so much more!
A ‘Choose Your Own Adventure’ is included in every surprise itinerary. In ‘Secrets of the South’ it included options for hiking, visiting an instagrammable spot, and a delicious winery. I was giddy with excitement the entire day. It was definitely a memorable day trip full of surprises!
Read more: Check out my second experience with Guess Where Trips with their one day road trip called Vistas, Falls & Caves
Gift A Trip
According to Forbes, the secret to happiness is spending money on experiences rather than things. So surely gifting experiences is the next best thing you can do! Guess Where Trips offers a ‘Gift-A-Trip’ gift certificate. Their gift card covers the cost of one of their one day surprise curated day trips. Either select one or allow the recipient to choose their own. I promise you the memories attached to this day trip are something your gift recipient will not soon forget.
As a holidaymaker…
Guess Where Trips far exceeded my expectations. Every little detail is carefully thought out and planned, right down to the cute packaging. Let Guess Where Trips plan your next day trip. Guess Where Trips is not only for locals looking to discover hidden gems in their own backyard, but it’s for tourists too. What a great way to experience the local area you are visiting in Canada. It’s bound to be a highlight of your trip!
Thank you to Guess Where Trips for gifting me with a free trip. As always, the opinions expressed are my own and I only recommend it if I absolutely love it, and I did!