Surprise Getaway from Toronto – Guess Where Trips Review

Surprise Getaway from Toronto – Guess Where Trips Review

Have you ever wanted to just getaway from Toronto for a day? 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 8 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 this post – we bought the service on our own and we’re giving our honest review of our own experience.


Surprise Getaway from Toronto – Guess Where Trip Review Contents
This post is lengthy. Here are some links to jump to the content you’re looking for. Enjoy!


What is Guess Where Trips?

Guess Where Trips is an Ontario company that produces curated itineraries that are theme-based, self-guided, and day-trip friendly and based on your trip style for $55.

Guess Where Trips Services

At the time of publishing, the company currently offers 8 getaways from Toronto and 4 getaways from Ottawa. The list continues to be improved upon and added to, so check back on their website for new getaways! (For those located in Vancouver, they have itineraries coming soon to you as well!)

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 from Toronto:

  1. Vistas, Falls & Caves – Explore the regions North-West of Toronto. The itinerary may include outdoor art, hikes, natural attractions, and a hidden gem of a winery.
  2. 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.
  3. 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”.
  4. 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”.
  5. 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.
  6. Hops & History – Get thirsty and head West of Toronto. Learn about some historical town facts while visiting some funky and up-and-coming breweries and wineries. You might even take a few short hikes along the way.
  7. 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
  8. 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.
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Guess Where Trips from Ottawa:

  1. Brews & Bites – 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. A Little Bit of Everything – Look to the East of Ottawa for a photo op at a country cafe. Eat some cute vegan snacks, go on a hike, and visit an outdoor attraction with something for everyone in this getaway from Ottawa
  3. 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.
  4. 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.
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 recently 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 does not include:

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

Our Guess Where Trips 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 out right. 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 anymore 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, a 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 and 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!

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!

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.

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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 colors 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 bottom of the falls. 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 favorite 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 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!

Was the trip worth it?

Guess Where Trips

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!

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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