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.

girl with laptop Guess Where Trips website

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 TownsTakes you to a historic village, a riverside trail and gorge
Funky Florals and Fine WinesMust love wine, food and flowers
Weird and Wonderful ThingsTakes you to a secluded waterfall and unusual attractions
The Small Town Charm TrailBrings you to quaint small towns full of charm
Outdoor Adventures & Scenic RoadsTakes you to cool attractions, good food and scenic roads
Bridges to BeachesOff the beaten path to sandy beaches and picturesque bridges
In GTA, London and Windsor area

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!

girl at mailbox with package from Guess Where Trips

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. 

girl with bag from Guess Where Trips

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.

open road with farm on Guess Where Trips

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.

girl in field on Guess Where Trips day
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 doing something I’ve never done before. The anticipation of the surprise secret day trip was definitely part of the thrill. 
girl with map Guess Where Trips
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 itinerary. I must say having a full exciting day already planned for you is an absolute pleasure and a welcomed change.
girl with camera Guess Where Trips
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.

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!  

Guess Where Trips envelope in field

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!

Guess Where Trips location tree and farm land

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.  

flowers with Guess Where Trips package
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. 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!

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51 Comments

  1. I have never heard of a trip planning website, but I am going to check it out 🙂 It seems to be very useful. Also, I would love to visit Ontario one day.

  2. What an interesting concept! I love surprises and love seeing new places. And love the research or learning about places when I get there. But having someone take over the planning part is really brilliant. Plus, the anticipation!

  3. 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

  4. 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!

    1. 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.

  5. 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.

  6. 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.

  7. 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.

  8. 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.

    1. 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.

  9. 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!

    1. 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.

  10. 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.

  11. 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.

  12. 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.

  13. 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.

    1. 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.

  14. 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.

  15. 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!

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