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Take a surprise day trip in Ontario with Guess Where Trips

August 19, 2020
Take a surprise day trip in Ontario with Guess Where Trips and discover hidden gems and picturesque places all in your backyard | My Wandering Voyage travel blog #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

Your bag is packed, and you jump in the car, ready for a road trip. But your destination? Well, that’s a secret! With Guess Where Trips, you can take a surprise day trip in Ontario and discover new destinations you may not have known about before. Would you do it? Would you toss aside planning and let someone else guide you?


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A big shout out to Guess Where trips for providing a free trip in exchange for this post. As always, options are my own and I won’t recommend anything unless I truly love it.



Take a surprise day trip in Ontario with Guess Where Trips and discover hidden gems and picturesque places all in your backyard | My Wandering Voyage travel blog #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

Let me tell you, that was hard for me. I’m a type-A planner. I have spreadsheets and maps that help decide where to go and what to see along the way. Setting out on a trip with no idea of where I was going and what I would see when I get there was nerve-wracking.

What is Guess Where Trips?

Guess Where Trips package | Take a surprise day trip in Ontario | My Wandering Voyage travel blog #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

Guess Where Trips wants to take all the planning and booking away from you and give you a fun, planned and surprise trip! The Ontario company creates curated itineraries based on the type of adventure you want to have and allows you to discover new places you may have never seen before.

They currently offer itineraries for a surprise day trip in Ontario.

How Does It Work?

The envelopes from Guess Where Trips | Take a surprise day trip in Ontario | My Wandering Voyage travel blog #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

First, you select your trip style. Guess Where Trips has several itineraries for a surprise day trip in Ontario, from adventurous areas to pretty places.

After selecting your trip and entering your contact information, you’ll have to wait for the surprise package to arrive in the mail.

The package includes a “before you go” guide that will give you all the need to know details without actually spilling the beans on where you’re going. You’ll also get your stop envelopes, which hold all the secrets within.

On departure day, you’ll likely want to leave early. Most of the day trips are within a couple of hours drive, but depending on where you are in the province, it could be longer. And the trips are a full day of adventuring. Meaning, you’ll want to hit the road early and get to your first stop.

Before you head off, open your first envelope and find out about your first destination and places to see along the way. Pack your day bag with comfy shoes, road snacks, sunglasses, a camera and some road trip tunes and get going!


RELATED: 25 best scenic lookouts in Ontario you have to see for yourself


What you need to know about Guess Where Trips

Frolicking in the Forest | Take a surprise day trip in Ontario | My Wandering Voyage travel blog #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

The cost of the surprise day trip in Ontario includes the planned itinerary but doesn’t include transportation, meals or entrance fees. There are several food stop recommendations, and I definitely recommend bringing some snacks for the drive.

You’re basically getting a fun, planned out itinerary with places you may not have head about before. For the cost, which is currently listed at $55 CAD, is totally worth it. I mean, I know how much goes into planning a road trip and having it all built for you, in a fun and exciting way, is worth every penny.

The price is not per person but per trip. So, if you want to bring a carload of people or head our on a solo trip, you’ll pay just one price for each trip you take. And it can be taken on any day (just double check on your “Before You Go” guide since some stops will be closed on some days of the week, or closed for the season), so if the day you plan to go is crappy weather, you can save it for a day with better weather.

If you’re terrible at secrets and can’t help but peek at where you’re going, there are maps available online using a unique code.


RELATED: 52 day trips from Toronto for every traveller


Surprise Day Trip in Ontario

Your Second Stop envelope | Take a surprise day trip in Ontario | My Wandering Voyage travel blog #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

Guess Where Trips offers at least eight different itineraries for a surprise day trip in Ontario, and they seem to keep growing. If you want to find hidden gems or if you’re looking for “instagrammable” places, there’s a trip for you. If you’re looking for a fun outing with your friends or a more fun outing with your significant other, there’s a trip for you. If you’re looking to discover new-to-you towns or new-to-you food stops, there’s a trip for you. Or if you want a complete surprise, then there’s a trip for you too!

Guess Where Trips offers the following itineraries for a surprise day trip in Ontario:

  • Outdoor Adventures and Scenic Roads: which offers hiking, countryside driving, and delicious food stops.
  • Funky Florals and Instagrammable Boardwalks: which offers wine, boardwalks and lots of flowers
  • Pretty Places and Country Favourites: which offers markets, lavender, beaches and more
  • Local Markets and Picturesque Towns: which offers picturesque towns and riverside fun
  • Wine Time and Hidden gems: which offers markets, restaurants and wine
  • Beaches and Breweries: which offers beaches, brews, food and paddling adventures
  • Taste of the Country: which offers a local farm experience, wine tasting, and picnics
  • Surprise me: which is for the spontaneous and indecisive who want a complete surprise.

Why go on a surprise day trip in Ontario?

Your Third Stop envelope | Take a surprise day trip in Ontario | My Wandering Voyage travel blog #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

There are so many amazing places in Ontario that go overlooked by those who want to visit the most popular sites, like the Bruce Peninsula, Niagara Falls and cottage country. From roadside stops to hidden gems, these secret trips will bring you to new and exciting places, all while playing a little surprise game.

Guess Where Trips is the perfect way to explore Ontario with your friends or significant other safely. It can be made the perfect gift for friends and family, or you can even treat yourself to a trip.

It’s so easy. You choose what type of adventure you want and They. Do. All. The. Work. For. You. I can’t stress how amazing it is to have a thoroughly planned trip without lifting a finger. I spend hours (sometimes days) crafting my trips to make it successful and enjoyable, but it was nice not having to do that at all and just enjoy the day.

I admit it was hard not to peek at where I was going! I am a type-A planner after all, and I just wanted to know. It was exhilarating to rip open the next envelope to see where I was going next.


RELATED: 22 best scenic bridges in Ontario you have to visit


My surprise day trip in Ontario

Beautiful building in a historic town in Ontario | Take a surprise day trip in Ontario | My Wandering Voyage travel blog #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

Without giving away too many details, I spent the day on the eastern side of Toronto, stopping at a lovely little town I had not heard of before. I enjoyed my time wandering the streets, drinking iced coffee from one of the recommended stops.

Takeaway Charcuterie Board | Take a surprise day trip in Ontario | My Wandering Voyage travel blog #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

Next was a hike where I could frolic in the forest, which is my happy place, but in a completely new area that, again, I had not heard of.

The third stop was a winery with an incredible view of the surrounding Oak Ridges Moraine landscape. But what I loved most was their takeaway charcuterie board. It was the best charcuterie board I have ever had.

Secret location on a surprise trip | Take a surprise day trip in Ontario | My Wandering Voyage travel blog #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

The last stop was another adorable small town I had actually been to before, so I dived into some of the surrounding recommended stops that are included in the itinerary and was pleasantly surprised with where I ended up.

Sorry (not sorry) the photos and descriptions are so vague, but if you want to see where these trips take you, you’ll just have to see it for yourself!

Take a surprise day trip

Guess Where Trips are listed as $55 CAD plus tax, but you can take 15% off with my code “MWV15” (expires Sept. 19, 2020) Go, enjoy the special day trip or gift it for a friend!


Take a surprise day trip in Ontario with Guess Where Trips and discover hidden gems and picturesque places all in your backyard | My Wandering Voyage travel blog #Travel #Ontario #Canada #SurpriseTrip #TripItinerary
Take a surprise day trip in Ontario with Guess Where Trips and discover hidden gems and picturesque places all in your backyard | My Wandering Voyage travel blog #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

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