Guess Where Trips creates exciting surprise Ontario day trips for you.

Ultimate Day Trips in Ontario with Guess Where Trips

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

Guess Where Trips creates exciting surprise Ontario day trips for you.

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.
From Toronto:

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.

From Ottawa: 

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

Guess Where Trips creates exciting surprise Ontario day trips for you.

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

Guess Where Trips creates exciting surprise Ontario day trips for you.

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

Guess Where Trips creates exciting surprise Ontario day trips for 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

Guess Where Trips creates exciting surprise Ontario day trips for you.
As a bit of a DREAMER, I thrive on having always something to look forward to. I love shaking up my normal routine and exploring a new-to-me place or do something I've never done before. The anticipation of the surprise secret day trip was definitely part of the thrill. 
Guess Where Trips creates exciting surprise Ontario day trips for you.
As a master PLANNER, I am always researching obsessively to find the best places to go and things to do. I was blown away by the planned intinery. I must say having a full exciting day already planned for you is an absolute pleasure and a welcomed change.
Guess Where Trips creates exciting surprise Ontario day trips for you.
As an EXPERIENCE collector, I am always on the hunt for new undiscovered places. I feel like I already know what southern Ontario has to offer. So, to my surprise, all but one of the four surprise stops I hadn't been to before. Guess Where Trips really does deliver on finding those hidden gems.
Guess Where Trips creates exciting surprise Ontario day trips for you.
Guess Where Trips creates exciting surprise Ontario day trips for you.

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). 

Guess Where Trips creates exciting surprise Ontario day trips for you.

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!

Guess Where Trips creates exciting surprise itineraries bringing you to new places in Ontario.

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!

Gift-A-Trip with a Guess Where Trips gift certificate which will allow someone to receive a surprise day trip in Ontario.

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. 

Guess Where Trips creates exciting surprise itineraries bringing you to new places in Ontario.
Guess Where Trips creates exciting surprise itineraries bringing you to new places in Ontario.

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!


  • Krista

    I have never heard of a trip planning website like this before! It makes road trips so much more fun and is such a unique idea. I’ll definitely look into them when I get back to Ontario later this year!

  • Raksha

    I am just like you, I am always on the research of finding new things or new places to discover at a place. I have not been to Ontario till date but would definitely want to go some day and explore the hidden gems. I will want to visit it for a longer period so I can spend sometime like a local.

  • barry

    These are very unique trips. I read the titles and the variety is immense and very enticing. I’ve never done a mystery tour like this but it appeals immensely to me as it looks like you have your own personal guide to all the sights on paper (or digital if you prefer).

    The “Local Markets & Picturesque Towns” one would be a must-do for me as my interest would lie mostly here.

    An advantage here is clearly to do this with a group of friends as the $55 for the package split betwen a group of 4-6 friends would be a really cheap way to have a fun day out.

    Great to see it covers several areas of Canada. Next year I’m off to see friends near Vancouver, BC and these trips would be a definite fun way to explore the areas with those friends who also do not know the area very well.

    • The.Holidaymaker

      Oh most definitely you’ll have to try it when you are in Vancouver. Barry you’ll appreciate that the surprise stops are chock full of interesting facts and history that makes seeing some of these sites even more interesting. You’re exactly right, it’s a great activity to do as friends, as it offers lots of variety to suit all interests, and cost effective.

  • Trisha Velarmino

    I also appreciate day trips! They can be a great source of discovery learning. What you’ve shared on your post is something I’ve heard of just now. It’s a wonderful concept! I’d love to be gifted with a curated trip. It’s nice to get surprised and thrilled with an unknown once in a while.

  • Linda (LD Holland)

    We were so glad we got to do so many road trips in Ontario over the last year. Always looking for new spots to head out to. I love the way the different types of road trip sights have been categorized! We too do a lot of research in advance for places to stop – so every drive takes so much longer than we planned! It would be fun to leave the planning to Guess Where Trips and see how that goes. Maybe for a fall adventure when we get back home.

  • Clarice

    This is exciting! Love that they had everything planned out for you. I would definitely avail of their service once we are back in Ontario. It’s cool that they will even provide a guide what to wear, pack or bring. What a unique and brilliant service.

  • Riana Ang-Canning

    This is so fun! I followed along on your trip on Instagram and thought it looked like such a blast. Love the tote bag and the next level touch of Spotify playlists too! So cool to hear they’ve expanded into BC. I’ll have to look into this – sounds like an awesome local adventure!

    • The.Holidaymaker

      You’ll have to definitely try it Riana! Your day will be full of surprises and jam packed with activities! I had such a great day! I can image the adventures you might have in the Vancouver one.

  • Eric Gamble

    As a Gen X-er you had me at the phrase “Choose Your Own Adventure!” This Guess Where Trips program sounds amazeballs! I love the whole concept though I wish it was in more places than just Ontario. No offense to our cousins up north but this would be amazing here in New Orleans too! I was literally talking about a similar program for major trips like this with a control freak friend of mine. He doesnt know if he could let go for a Pack Up & Go type program but I told him it was probably what he needs cause he never ever goes anywhere due to his control issues.
    If I was in Ontario though, I think I would probably choose the Quirky Adventures and then the Hops & History options first though I do say that Local Wonders would be very cool too.

    • The.Holidaymaker

      Well, you never know if they might expand! It’s a cool concept and so much fun. It plans out so many activities throughout the day that it suits all interests especially if you are going with friends. Maybe you’ll just have to come to Toronto and try one.

  • Natascha

    The “Guess where trips” really sounds like a fun concept to spend a day near Toronto or Ottawa exploring new things. I like that you can choose the direction of the trip, but still have the surprise moment of the itinarary. It would be nice if they also offer trips by public transport.

  • Manjulika Pramod

    Very well said, one must spend money on experiences than things. I loved the pictures and inspiration to take those one day trips. ‘Guess where trips’ sound like the perfect thing for these pandemic days. A trip full of surprises would be great for the family too. Thank you for this refreshing post.

  • Ambica Gulati

    There’s a lot that can be done in a day! Your itinerary and planning was superbly done through Guess Where Trips. I liked their attention to detail. Your pictures make it look like such a happy day trip. Am sure it would be fun to replicate something like this in India too.

  • Jennifer Prince

    A surprise itinerary is such a fun idea! I’ve been to Ontario a few times but only to see Niagara Falls and Niagara on the Lake (b/c I’m obsessed with the Falls basically, ha!). I’d love to travel again and see what else Ontario has to offer!

    • The.Holidaymaker

      You’ll definitely have to give them a try next time you are cross the border. I couldn’t think of a better way to see some of Ontario’s hidden gems – that are beyond the falls. Thanks for stopping by and commenting.

  • Emma

    I love this concept. I’m always looking for somewhere new to visit, or even new recommendations for a place I’ve been to before. This would be such a great experience, I like surprises so the mystery of it has me intrigued. Kind of like those surprise flight itineraries I’ve seen

    • The.Holidaymaker

      This is a great company who has planned safe day trips to hidden gems especially since we can’t travel to far yet. Perfect for locals who want to discover places close by.

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