Surprise Getaway from Toronto – Guess Where Trips | Ontario Review

Surprise Getaway from Toronto – Guess Where Trips | Ontario Review

Have you ever wanted to just plan a getaway from Toronto for a day? Or have you ever wanted to plan a surprise trip for your partner? And have you ever suddenly decided against taking that getaway because:

  • it was a long week and you just don’t have the energy to plan that getaway
  • you want to go *somewhere*, but not enough to actually research places to go for it
  • you’re bored of your own local travel ideas (I get it, some days I don’t really want to go hiking, but I can’t think of anything else to do either!)
  • you feel like you already know what all of Southern Ontario has to offer

then you might want to consider trying one of the curated itineraries created by Guess Where Trips.

COVID Updates:
Due to COVID, everything related to travel is changing. At the time of publishing, travel in Ontario is restricted. Please refer to: Reopening Ontario for more details.

Disclaimer: SYDE Road was not sponsored or commissioned to create or update this post – we bought the services on our own and we’re giving our honest review of our own experience.


Looking for other day trips near Toronto? Here are some posts you may like!


Surprise Getaway from Toronto – Guess Where Trip Review Contents
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Last Updated: October 9, 2021

What is Guess Where Trips?

Guess Where Trips is an Ontario-based company that produces curated itineraries around Canada that are

  • theme-based
  • self-guided and
  • day-trip friendly (with options to make it overnight!)

all for $55. The kicker? All the road trips don’t tell you the destinations! Every itinerary is essentially a mystery road trip somewhere in Canada.

Need a bit of convincing? Check out this quick summary from our second Guess Where Trips!

Guess Where Trips Locations

At the time of publishing, the company currently offers surprise road trips that start from: Calgary, Halifax, Toronto, Ottawa, London, Windsor, Winnipeg, and Vancouver.

The list continues to be improved upon and added to, so check back on their website for new getaways!

For today’s post and review, I will be focusing on the road trips offered in Ontario… because well that’s where I live!

The dog-friendly adventures are highlighted in green below. While most of the available getaways are labelled as dog-friendly, some of the itineraries may have restrictions at food places or specific stops.

If you’re not certain about an itinerary, you can definitely contact Guess Where Trips to make sure that the itinerary is 100% dog-friendly.

Guess Where Trips around Toronto:

  1. Wine Time and Hidden Gems – Look to the East of Toronto. Includes an iconic market, a scenic boardwalk, some quirky & cute wineries, a ‘Ghost Town’, and a few hikes along the way.
  2. Weird & Wonderful Things – Head North of Toronto. You might sightsee waterfalls, go on hikes, go through a town with hidden outdoor art, and visit a place ranked as “one of the world’s most bizarre places”.
  3. The Waterfall Route – Head north and escape the Hamilton waterfall road trippers. Discover new waterfalls, scenic views, new small-town food shop favourites, and a one-of-a-kind seasonal garden
  4. Historic Haunts – Get spooky driving West of Toronto. Visit haunted schools, post offices, hikes, graveyards, ghost towns, and several other locations with a haunted past.
  5. The Butter Tart Trail – In the mood for butter tarts? Take this surprise road trip and head East of Toronto to enjoy some country farms, country bakeries, picturesque historic buildings and ruins, and some cottage country towns all while devouring as many butter tarts as you can!
  6. The Fairy Tale Trail – Live in the GTA, Niagara, or Kitchener-Waterloo area with kids under 12? This is the ideal mini road trip to complete with your children. Transport your child and let their imagination run wild as you visit waterfalls, castle grounds, and wildlife in this stroller-friendly road trip.
  7. The Whimsical Route – Another mini road trip designed for families with children over the age of 5 that live in the GTA, Niagara, or Kitchener-Waterloo area. This trip will take you on a number of easy outdoor adventures that provide a variety of kid-friendly options at each stop. There’s even a scavenger-style activity throughout the itinerary to keep your kids engaged!
  8. Bridges to Beaches – Look to the North-West of Toronto for hikes, pretty beaches, a seasonal waterfall spot, and maybe some alpacas and goats too! You’ll love the bridges in this itinerary that are perfect for a photo-op too.
  9. Taste of the Country – Discover scenic towns, do a waterfront photo op, and enjoy some cute, family-friendly farms when you head west of Toronto on this road trip!
  10. Funky Florals and Fine Wines – Head to the regions South-West of Toronto. The itinerary might bring you through a floral wonderland, wineries, and a cute Canadian Town.
  11. Local Markets & Picturesque Towns – Drive West of Toronto. Includes historic towns with great local markets, a picturesque surprise stop, beautiful gorges and riverside walks, and stopping at “the most beautiful village in Canada”.
  12. Outdoor Adventures – Head North-East of Toronto to get away from the crowds. Go to a cute town with a few surprises, take a short hike, visit an Italian winery, and ogle at some pretty countryside driving
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Guess Where Trips around Ottawa:

  1. Brews, Bites, and Everything Nice – Explore the South-West regions of Ottawa. Enjoy a couple of adorable cafes and shops. Stroll through a variety of different breweries & distilleries, and maybe take a few photos as some of the spectacular photo opportunities in this itinerary
  2. Quirky Adventures – Go South of Ottawa for this adventure. Maybe visit adorable towns, look at beautiful views at a boardwalk, see some old mill ruins, and drive-by a very cool photo opp. You might even have some forest bathing opportunities too.
  3. Local Wonders – Discover some hidden gems within the city’s limits! Look forward to some insta-worthy photo ops, funky restaurants, and some classic treasures you might just have forgotten about!
  4. All the Pretty Things – Looking for stunning viewpoints, delicious restaurants and wineries? Then check out this surprise road trip itinerary!
  5. Views & Secret Stops – Look for an underground tunnel south of Ottawa. Then, go on scenic hikes, visit a craft cidery, a waterfront town, and head to numerous viewpoints and photographic opportunities with this itinerary.
  6. Backroad Bliss– Perfect for folks who live anywhere between Ottawa and Montreal! This secret travel itinerary takes you from waterfalls and hikes to ridiculously cute towns and shops. There’s a little bit of everything to be enjoyed on this trip!
Guess Where Trips - Limone in Background

Don’t Peek! Your destinations are sealed!

I love that Guess Where Trips mails you the itinerary in several sealed envelopes. How cute and unique! Like the company’s name implies, you really only find out where you’re going once you get to each stop in the itinerary.

The package includes:

  • a ‘before you go’ envelope that gives you all the details you need to know about your day trip (spoiler-free details!)
  • several numbered envelopes

Each getaway, including driving time, is generally 6-8 hours long so you’re definitely in for a full day of adventuring regardless of which adventure you choose.

What you get when you buy Guess Where Trips

What does the $55 include?

When you purchase a Guess Where Trips itinerary you get the following:

Note: as of June 2, 2020, Guess Where Trips rebranded and upgraded the experience. You’ll still receive the sealed envelopes, but they’re coming in redesigned envelopes and instead of pamphlets, they’ve been upgraded to super pretty booklets!

  • Detailed before you go pamphlet
  • A planned itinerary with recommended driving hours and destination hours
  • Recommended breakfast/café and lunch locations
  • Optional stops in each itinerary
  • Updated information on travel restrictions to destinations (including any restricted weekend or weekdays due to business operating hours)

What is not included?

The Guess Where Trip services do not include:

  • Costs incurred for going on the getaway itself including gas, food, drinks
  • Admission fees to the suggested locations in the itinerary

Guess Where Trips Reviews – Our Experience (spoiler-free)

Guess Where Trips

I started guessing a few weeks before we went

The surprise and anticipation of a Guess Where Trip can begin way before your trip if you plan it outright. For me, the guessing experience started several weeks before we even started the trip. Out of the blue, Angelo asked me to block a full day off for an extra special date.

It doesn’t have to be any special day… we can do it whenever, but it does need to be a full day. Oh and wear comfy but cute clothes.

Angelo being tightlipped when I asked where we were going

Talk about mysterious! So here’s the thing about me. I love guessing things. I love guessing movie endings before starting a movie, guessing where we’re going and even guessing my birthday or Christmas gifts before I get them. I love it so much that Angelo has had to impose a ‘guess 3 times only’ rule to keep me from talking his ear off! Having a very tightlipped partner meant that I wasn’t going to get any more hints.

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Hmm.. since he said that ‘it doesn’t have to be any particular day‘ that probably meant it wasn’t holiday-related, concert-related or any special event-related activities like Rib Fest. But the full-day part really got me thinking… alas, I really didn’t have much to go on!

Maybe a winery somewhere? Or a hike at one of the provincial parks? Hmm but the ‘comfy AND cute’ part doesn’t seem like it could be a hike either (I don’t own ‘cute’ hiking clothes.. they’re all sweats!). I was stumped!

Revealing the Surprise and Receiving the Package

A few days later we received a non-descript brown package in the mail. It was just large enough to hold a book. Turns out the package was for the full day date! Now my thoughts were racing. Maybe we were going to a concert after all? Hmm but this was October 2020, during COVID restriction times, there’s no way there’d be a concert right now. Something that only the two of us could do… Maybe it was one of those date book ideas and we would spend the day going through it? I was still stumped.

By now, we had already decided on a date and my not-so-discreet search attempts on the Internet for upcoming events resulted in.. no answers. I was still doing to have to wait and find out what we were doing.

My project manager tendencies were really itching. I needed to make a plan for our date, but I couldn’t.

I’m not opening this until the night before. No more guessing.

Angelo to me when I tried to exceed my 3 guess limit
Guess Where Trips Package

Finally the reveal

The night before our scheduled date night had finally arrived.

We opened the mysterious brown package. I was finally going to find out what we were doing. Imagine my surprise when I found out we were doing a getaway from Toronto and that Angelo, the one who ‘planned’ this date, didn’t know what we were doing either!

All he knew was that we were in for an interesting and possible weird experience – he bought Guess Where Trips’ Weird & Wonderful Things for us to try out. I LOVE weird and quirky things so I literally could not wait to head on out and do this trip! Alas, I needed to wait one more night before I could 🙁

We read the ‘before you go’ envelope and followed the instructions. We packed some money and picked out some clothes for our date. It was pretty clear that we would be driving for a while. There was also something about donating a can of goods at one of the locations… but ironically enough we didn’t have any canned goods in our house that day, so we made a mental note to stop by somewhere on our date day.

Our Trip Experience

Guess Where Trips - First Stop
Our first stop was at a café in a picturesque town

To keep the experience as spoiler-free as possible – this part is purposely going to be vague. We started our day off early-ish at about 9 AM, stopping by McDonald’s for some breakfast. The itinerary listed out several cafes for the day but as they were an hour or so away, we figured that eating breakfast first and then stopping at the cafes to enjoy a coffee would be better for our hunger.

Our itinerary took us north to a cute town with a unique café. We weren’t able to linger at the café because of COVID travel policies and drank our coffee outside. Unfortunately because of this, we weren’t really able to appreciate their unique interior design for more than a few minutes as we waited for our coffee to brew.

At this point, we met a family of four who also stopped by this cafe. As they bought their cookies and headed back to the car, we noticed they were clutching the same Guess Where envelopes as us! So as you go on these itineraries, keep your eyes peeled as you may see fellow Guess Where adventurers around you too!

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Next, we stopped at a cute town (not pictured to keep things spoiler-free!) with a waterfall before opening our next envelope. We entered the address into our GPS and away we went.

Guess Where Trips Scenic Viewpoint

Our next stop took us to a populated scenic viewpoint of the area where we got to enjoy the fall colours the area had to offer. The envelope did mention that this particular location was a perfect place to enjoy a lunch break, but we decided to stop by one more optional hike activity before trying one of the three lunch places offered in the itinerary.

To be honest the optional hike was gorgeous! We liked this hike better than the waterfall listed in the main itinerary. It was a slightly secluded, tall, and beautiful waterfall nestled at the end of a short trail. We had the option to head to the top of the falls as well as enjoy a short walk to the falls’ bottom. There was practically nobody there and it felt like we had the falls all to ourselves that day.

Afterwards, we went for lunch at one of the recommended locations, and again due to COVID restrictions, we had to get takeout and eat it outside, but the food was delicious. At this point we needed a canned food donation, so we stopped by a gas station to pick one up before heading to our last and final stop, an outdoor park.

To be honest our last stop at the outdoor park was our favourite location and it pains me so much that sharing any additional photos will immediately reveal the location and give away the surprise. Our Guess Where Trips itinerary truly saved the best for last and I really wish they allotted more time for this last stop. We arrived at this area by the late afternoon/ early evening and honestly, we could have spent an extra hour here if we could!

Guess Where Trips

Was the trip worth it?

The short answer? Yes. We LOVED that we there is a service that takes the planning out of day trip. Something about opening a sealed envelope to reveal directions to your next destination is SO SATISFYING. I love it so much that I might even be tempted to re-create something like this next time I plan a day trip for ourselves!

For $55.00, Guess Where Trips takes the planning out of the trip and fully allows the entire party to enjoy the trip with minimal planning. Overall we found the itinerary to be:

  • accurate with estimated driving times
  • accommodating – offering several meal options to cater to dietary restrictions or cravings
  • flexible – since this is self-guided you can stay at each stop for however long you’d like and pick and choose the optional items to best suit your day needs
  • dog-friendly – we didn’t try this with Limone since it was a humans-only date day, but after going through it, we’d love to try a new experience and bring Limone to the other dog-friendly options!

What I like the most about this service is that everyone on the trip gets to experience the joy of guessing where the next location will be and reacting to the place once we get there.

The price tag isn’t even a per-person experience – it’s the cost of each itinerary, meaning you’re not restricted to the number of people you take to experience it. Next time, I’d really love to do this again and bring Limone and my friends and family with us too!

[Update: October 9, 2021] Surprise surprise! We loved it so much we bought one experience for our relatives and bought another to experience for ourselves again!

Two years later, we went on another fall road trip around Ontario with Guess Where Trips. Our verdict? Still freaking awesome! Other than the updated packaging and added itineraries, the heart and soul of Guess Where Trips remains the same. Guess Where Trips continues to consistently curate and deliver itineraries that:

  • are educational
  • are fun to explore
  • support a plethora of local businesses
  • inspire and prove that local travel can be just as exciting and fun as international travel

My verdict remains the same! 100% recommend trying at least one trip, if not several! I promise you’ll discover some new hidden gems that you’ll love!

In the theme of keeping things a surprise, I won’t be listing out any locations for updated Guess Where Trip pictures – but feel free to enjoy our new photos 🙂

So what do you think? Will you give Guess Where Trips a try as well? If you did, I’d love to hear your experience of the trip as well!

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Maria is the founder of SYDE Road, a blog about adventure and often-times dog-friendly traveling. She loves researching and planning for trips and is the 'project manager' for many of the small group adventures documented on this blog. She believes that while it is always best to go into a trip with a plan, the best planned trips are always the ones that have time built-in to explore and get a bit lost. Her itineraries are detailed with safety hints and tips, but are also peppered with unique travel stories and experiences that are the result of free time, getting lost, or stepping off the main trails. She aims to inspire others and give people the confidence to travel the world and get a bit sidetracked!

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