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 comes along and takes you to some new hidden gems!

Let me share how it works, and my experience using Guess Where Trips, more than once!

How does Guess Where Trips Work?

1. Choose Your Day Trip

girl with laptop Guess Where Trips website

The first step from the Guess Where Trip website involves selecting a one-day road trip tailored to your unique interests and preferences. You can factor in essential elements like driving time from your starting location.

Whether you’re a history and culture enthusiast, a beach lover, a fan of charming towns, or an avid hiker, there’s a road trip experience waiting for you.

You have the option to filter your choices based on specific needs. Are you travelling with a wheelchair? Seeking vegan-friendly options? Exploring with your family or furry friend in tow? No worries – Guess Where Trips has you covered.

Or, if you want to leave it up to them, take the road trip quiz to see what suggested trips are best for you.

Each mystery day trips Ontario package is designed with utmost care and attention to detail. The best part? You won’t know your exact destination until the day of your adventure. It’s a delightful twist that keeps the excitement alive.

These trips are concentrated in key regions of Ontario, spanning from the charm of southwestern Ontario (Windsor to London) to the vibrancy of central Ontario (Toronto) and the historical appeal of eastern Ontario (Ottawa).

Guess Where Trips takes the burden off your shoulders in planning an exciting day trip. They meticulously research and plan each itinerary, ensuring that your day is filled with delightful surprises and memorable experiences.

For only C$65, you can embark on a one-day surprise road trip that’s bound to leave you with cherished memories.

To make things even more convenient, you have the option to get their PDF package for $39. However, for those seeking the full experience, receiving the package in the mail is a treat in itself. The packages are not only filled with valuable information but also arrive in charming packaging, adding a touch of anticipation and excitement to your journey.

Guess Where Trips Locations

Guess Where Trips are found in the following locations:

  • Ontario trips include the 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, in many Eastern states (FL, GA, NC, DMV, NY, NJ, PA, CT) of the USA

Best Selling Guess Where Trips Ontario

Here’s a small sample of their cute day trips that are near Toronto (In GTA, the London and Windsor area)

Local Markets and Picturesque Towns

Funky Florals & Fine Wines

Weird & Wonderful Things

The Small Town Charm Trail

Outdoor Adventures & Scenic Roads

Bridges to Beaches

Takes you to a historic village, a riverside trail and a gorge

Must love wine, food and flowers

A secluded waterfall and unusual attractions

Brings you to quaint small towns full of charm

Takes you to cool attractions, good food and scenic roads

Off the beaten path to sandy beaches and picturesque bridges

2. Get your Package

girl at mailbox with package from Guess Where Trips

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 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

girl with bag from Guess Where Trips

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 Mystery Trips Ontario Adventure Awaits

open road with farm on Guess Where Trips

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 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

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 that 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.

Guess Where Trips location tree and farm land

In ‘Secrets of the South’ there are options for hiking, visiting an instagrammable spot, and a delicious winery. I was giddy with excitement the entire day. It was a memorable day trip full of surprises!

Gift A Trip

flowers with Guess Where Trips package
Hint, hint to my family and friends, I would love to do this again!

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.  

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 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!