girl in field on Guess Where Trips day

Mystery Day Trips with Guess Where Trips Ontario

Are you a big fan of day trips? There’s just something about hitting the open road and visiting a different place for a day. Let me introduce you to Guess Where Trips! A local Ontario company that is redefining road trips. They create exciting surprise itineraries that take you to new places you’ve never been before.

Just when you thought you knew every quaint little town or hiking trail or historical site Guess Where Trips Ontario comes along and takes you to some new hidden gems!

In this article, I’ll share how it works, my experience and my Guess Where Trips review. (Updated for 2023)

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 mystery day trips Ontario package 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. Or, get their PDF Instant Download for $39CDN. Personally, it’s a better experience to get the package in the mail, as there is so much info contained in these packages, not to mention the cute packaging you get to open.

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
  • And, Florida USA (*newest location in 2023)

Best Selling Guess Where Trips

Here’s a small sample of their cute day trips that are near Toronto.

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.

I had so much fun on this mystery road trip I did a second one called Vistas, Falls & Caves.

Don’t believe me, just take a look at these Guess Where Trips Ontario reviews, they are glowing!

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 all mystery trips Ontario surprise itineraries.

In ‘Secrets of the South’ there’s 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

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 surprise road 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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