I’m a big fan of day trips. There’s something about exploring a different place for a day – even if it’s just the next town over… it has always appealed to me. Luckily, Ontario has so many great options for day trips. Whether it’s visiting a quaint town, or exploring hiking trails and lakes, or going to museums and cultural sites – the list is endless.
For any memorable day trip, it requires research and planning, and that equals time. And, who has that kind of time? Let me introduce you to Guess Where Trips, an Ontario company that creates exciting surprise itineraries that take you to new places you’ve never seen before.
Choose Your Day Trip
The very first step is to select a day trip based on your interests and preferences. This can include driving time from your starting location and attractions that appeal to you, such as, history/culture, beaches, cute towns, and hiking to name a few. Additionally, you can filter by accessibility, whether that be wheelchair, vegan, family oriented or dog-friendly. Or, simply take the road trip quiz to see what suggested trips are best for you.
Each trip includes a curated surprise intinery, so 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, it’s very affordable. Each day trip is only C$55.
Here are a select few day trips.
Local Markets & Picturesque Towns is one of their best-selling trips that takes you to a historic village, riverside trail and a gorge.
Bridges to Beaches is a new trip that takes you to some scenic bridges and sandy beaches and a funky cafés in between.
Hops & History takes you to some cool up-and-coming breweries and wineries and historical towns.
Secrets in the South is a new trip that takes you to some country markets and eateries, a cute hamlet and a beach town.
All the Pretty Things is a new trip offering a variety of experiences from cute eateries to seeing some beautiful sights.
Views and Secret Stops is all about the views from a scenic drive to hiking vistas and visiting a charming town.
Local Wonders is a new trip full of mini adventures promising lots of photo-op moments.
Quirky Adventures is a locals favourite as it takes you to some unique spots like forest bathing, an old mill ruin.
Get your Package
Now that you have chosen your trip you’ll have to wait for the surprise package to arrive in the mail. There’s really no better feeling than opening the mailbox to find a package has arrived! Such a simple thing, yet it brings so much joy.
In your package you will receive 5 envelopes – a ‘Before You Go’ plus four secret intinery 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 intinery)
- 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/kms)
- frequently asked questions specific to your day trip
Pack your Bags
Your bag is packed, you’re ready to jump in the car and hit the open road, but before you do, open ‘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 your first destination into your GPS, and don’t forget every road trip needs some good tunes. Guess Where Trips has even supplied you with road trip playlists on Spotify. Ok, now you’re ready – let’s go!
Your Adventure Awaits You
Every curated intinery will bring you to four destination areas. Each of the four stops are packed with information, travel tips, and maybe even some exclusive Guess Where Trips discounts at 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 is still a great feeling of it being carefree and spontaneous. It’s the element of surprise!
My Guess Where Trips Experience
As much as I am eager to share the details of my wonderful day trip, I hate to spoil the surprise for you. All I will say is that my trip 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, and going to a town with some historical attractions (and so much more).
Additionally, a ‘Choose Your Own Adventure’ included a mix of 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!
Gift An Experience
According to Forbes, the secret to happiness is spending money on experiences rather than things. So surely gifting experiences is the best thing you can do!
Well, you’re in luck as Guess Where Trips offers a ‘Gift-A-Trip’ gift certificate. Their gift card covers the cost of one of their 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 they’ll never forget.
Hint, hint to my family and friends, I would definitely love to do this again!
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. They have recently expanded to BC and Alberta, and are considering expanding to other provinces in Canada. I would definitely recommend this, not only to locals, but to travellers visiting Ontario. It’s a great to learn, discover and support local communities.
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 if I absolutely love it, and I did!