Take a surprise day trip in Ontario with Guess Where Trips
Your bag is packed and you jump in the car, ready for a road trip. But your destination? Well, it's a secret! With Guess Where Trips you can take a surprise day trip to Ontario and discover new destinations you may not have known before. Would you do it? Would you like to put planning […]

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


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Many thanks to Guess Where Voyages for providing free travel in return for this post. As always, the options are mine and I won't recommend anything unless I really like it.



Take a Surprise Day Trip to Ontario with Guess Where Trips and Discover Hidden Gems and Scenic Places in Your Backyard |  Travel Blog My Wandering Voyage #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

Let me tell you, it was difficult 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. Going on a trip with no idea where I was going and what I would see when I got there was scary.

What is Guess Where Trips?

Guess Where Trips Package |  Take a Surprise Day Trip to Ontario |  Travel Blog My Wandering Voyage #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

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

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

How it works?

The envelopes of Guess Where Trips |  Take a Surprise Day Trip to Ontario |  Travel Blog My Wandering Voyage #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

First of all, you select your travel style. Guess where the trips offers several routes for a surprise day trip in Ontario, from adventurous regions to pretty places.

After selecting your trip and entering your details, you will need to wait for the surprise package to arrive in the mail.

The package includes a 'before you go' guide that will give you all you need to know the details without really spilling the beans on your destination. You will also get your stop envelopes, which contain all the secrets.

On the day of departure, you will probably want to leave early. Most day trips are a few hours' drive away, but depending on where you are in the province it could be longer. And the trips are a full day of adventure. This means you'll want to hit the road early and get to your first stop.

Before you go, open your first envelope and learn about your first destination and the places to see along the way. Pack your day pack with comfy shoes, road snacks, sunglasses, a camera and road trip tunes and get started!


RELATED: 25 Best Scenic Views In Ontario You Must See For Yourself


What you need to know about Guess Where Trips

Frolic in the forest |  Take a Surprise Day Trip to Ontario |  Travel Blog My Wandering Voyage #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

The cost of the Surprise Day Trip to Ontario includes the planned itinerary but does not include transportation, meals or entrance fees. There are several food stop recommendations, and I definitely recommend bringing some snacks for the ride.

Basically, you get a fun, planned route with places you might not have experienced before. For the cost, which is currently listed at CAD $ 55, it's definitely worth it. I mean, I know how much it takes to plan a road trip and build it all for you, in a fun and exciting way, worth every penny.

The price is not per person but per trip. So if you want to take a car full of people or take a solo trip, you will only pay one price for each trip you take. And it can be taken on any day (just check your 'Before You Go' guide as some stops will be closed on certain days of the week or closed for the season), so if the day you plan to go is no weather, you can save it for a day with better weather.

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


RELATED: 52 day trips from Toronto for each traveler


Surprise Day Trip to Ontario

Your Second Stop envelope |  Take a Surprise Day Trip to Ontario |  Travel Blog My Wandering Voyage #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

Guess Where Trips has at least eight different routes for a surprise day trip to Ontario, and they seem to keep growing. If you want to find hidden gems or are looking for “Instagrammable” places, there is a trip for you. If you are looking for a fun outing with your friends or a more fun outing with your other half, there is a trip for you. If you are looking to discover new cities or new restaurants, there is a trip for you. Or if you want a complete surprise, there is a trip for you too!

Guess where the trips offers the following routes for a surprise day trip to Ontario:

  • Outdoor adventures and scenic routes: which offers hiking, country driving and delicious food stops.
  • Funky Flowers and Instagrammable Walks: which offers wine, walks and lots of flowers
  • Nice places and favorites of the country: which offers markets, lavender, beaches and more
  • Local markets and picturesque towns: which offers quaint towns and riverside entertainment
  • Wine Time and hidden gems: which offers markets, restaurants and wine
  • Beaches and brasseries: which offers beaches, breweries, food and paddle adventures
  • Taste of the country: which offers a local farm experience, wine tastings and picnics
  • Surprise me: which is aimed at the spontaneous and undecided who want a total surprise.

Why take a surprise day trip to Ontario?

Your third stop envelope |  Take a Surprise Day Trip to Ontario |  Travel Blog My Wandering Voyage #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

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

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

It is so easy. You choose what kind of adventure you want and them. Make. All. The. Job. For. You. I can't stress how amazing it is to have a well-planned trip without lifting a finger. I spend hours (sometimes days) designing my trips to be successful and enjoyable, but it was good not to have to do that at all and just enjoy the day.

I admit that it was difficult not to see where I was going! I'm a Type A planner after all, and just wanted to know. It was exhilarating to tear up the next envelope to see where I was going next.


RELATED: 22 Best Scenic Bridges In Ontario You Must Visit


My surprise day trip to Ontario

Beautiful building in historic Ontario |  Take a Surprise Day Trip to Ontario |  Travel Blog My Wandering Voyage #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

Without going into too much detail, I spent the day in East Toronto, stopping in a charming little town that I hadn't heard of before. I enjoyed my time wandering the streets drinking iced coffee at one of the recommended stops.

Take away cold cuts board |  Take a Surprise Day Trip to Ontario |  Travel Blog My Wandering Voyage #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

Then there was a hike where I got to frolic in the forest, which is my happy place, but in a completely new area that, again, hadn't heard of.

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

Secret place on a surprise trip |  Take a Surprise Day Trip to Ontario |  Travel Blog My Wandering Voyage #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

The last stop was another lovely little town I had been to before, so I dove into some of the recommended stops in the area that are included in the itinerary and was pleasantly surprised at where I was. found myself.

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

Take a surprise day trip

Guess where the trips are listed at CAD $ 55 plus tax, but you can take 15% off with my code "MWV15" (expires September 19, 2020) Come on, enjoy the special day trip or gift it to a friend!


Take a Surprise Day Trip to Ontario with Guess Where Trips and Discover Hidden Gems and Scenic Places in Your Backyard |  Travel Blog My Wandering Voyage #Travel #Ontario #Canada #SurpriseTrip #TripItinerary
Take a Surprise Day Trip to Ontario with Guess Where Trips and Discover Hidden Gems and Scenic Places in Your Backyard |  Travel Blog My Wandering Voyage #Travel #Ontario #Canada #SurpriseTrip #TripItinerary

One of my biggest regrets from the first year of my travels was that I wasn’t brave enough to try any of the local food. I was raised a picky eater and that, combined with debilitating anxiety and an eating disorder, led to me believing that I would either hate or be allergic to anything I hadn’t tried before. I love trying new things, and I’ve found a thousand amazing dishes that I never would have discovered if I’d continue to eat from supermarkets around the world. Trying new food isn’t scary, and you’ll build your confidence up as you fall in love with more and more things.

One of the first lessons I learned on the road was that your plans will nearly always change. You’ll arrive in a place and hate it and want to leave immediately, or you’ll fall in love with a destination and want to spend longer there. You’ll make friends with a group of awesome people and want to change your partouze so you can travel with them for longer, or you’ll find out about an amazing-sounding town that’s nearby and want to head there instead.

Sure, you should have a rough plan for your trip, but don’t book everything in advance or you’ll likely feel too restricted and end up regretting it. Book a one-way ticket and your first few nights of accommodation — you’ll figure the rest out along the way. It’s not as intimidating as it sounds. If you’re in a tourist destination there’ll always be someone who’s willing to take your money by giving you a place to stay.

If you do only one thing before you leave, make it getting travel insurance. I’ve heard far too many horror stories of travellers injuring themselves in remote places and ending up in hundreds of thousands of dollars worth of debt. Don’t think that it won’t happen to you, because you know those travellers thought that, too. I’ve use World Nomads for my travel insurance provider for six years and recommend them to everyone I know. They were fantastic to deal with when making a claim.

People laughed at me when I said that I was carrying around a dozen spare passport photos, but they’ve been incredibly useful and saved me a ton of time and hassle. Who wants to wander the streets of some rural town in Cambodia searching for someone who can take your photo ? Friends of mine had to do this !

I’ve used them to apply for visas around the world, to get a new passport when mine expired while I was on the other side of the planet, and I even needed one to buy a local SIM card in Nepal ! Having spares in my backpack meant that I didn’t have to waste a day researching and then wandering around a city to try to find someone who could take a passport-sized photo of me.

I’m fortunate to have never had to deal with lost luggage, but I did have my backpack ripped open on a flight and I was grateful to have not had anything valuable in it at the time. I’ve also been on dodgy buses in Southeast Asia where we’ve arrived at our destination and people have had items stolen by someone hiding out in the luggage hold while we were transit.

If there’s anything I’d be upset to lose, I keep it in my daypack, which is always by my side on travel days. For me, that’s my passport, laptop, camera, external drive, a debit card, and some spare cash. As long as I have all of these, I can survive indefinitely.

When you travel, you’re in the sun more than most people thanks to months of island-hopping and beach time, as well as entire days spent outside exploring. Wear sunscreen every single day, regardless of the weather and temperature, because you really don’t want your trip of a lifetime to result in skin cancer or a body that’s blanketed in leathery wrinkles.

There have been so many times when I’ve been too shy to ask someone to take my photo in a place and I’ve almost always regretted it. After eight years of travel, I probably only have around 200 photos of me around the world. Photos of the beautiful places you visit are great and all, but when you get home, they’re not all that different to the ones everyone else has taken there, too. Photos with you in them are special and they’ll mean a lot more to you when you look back at them. You’ll gain more respect from the locals if you can at least say hi, please, sorry, and thank you. On that note, remember : if you don’t speak the language, it’s your problem, not theirs. And please don’t start speaking louder to make yourself understood. Try miming instead, or using a translation application on your phone.

Travel isn’t conducive for sleep, whether it’s snorers in dorm rooms, early risers rustling plastic bags, or drunk backpackers stumbling around in the middle of the night. Even if you don’t stay in hostels, you’ll still have to deal with street noise from outside, loud bars nearby, and uncomfortable overnight journeys. Pack some ear plugs and a sleep mask in your bag to help improve your sleep. I’ve been using Sleep Phones to block out light and listen to podcasts and I love them.

I’d always been all about the packing cubes, until I discovered vacuum-sealed variantes of them ! You throw your clothes in, seal the bag, then roll it up to push out all the air. I can literally fit twice as many clothes in my backpack when I use these ! Even if you don’t want to carry more things in your bag, it frees up so much space that if you need to pack in a hurry, you can just chuck everything in.

Sometimes your bank will block your card, sometimes your card won’t work in an ATM, and sometimes you could even lose it or have it stolen. Bring at least three debit/credit cards with you that are all linked to different accounts ( with money in them ! ) Keep one in your backpack, one in your daypack, and one on your person.

I carry a spare 300 USD that’s split up in various places in my backpack, daypack, and occasionally, my shoe when I’m nervous I’ll be robbed. It means that in a worse-case scenario, I can pay for some food, a dorm bed, and a Skype call to my family to get an emergency wire transfer until I can get back on my feet again. I went with U. S. dollars because it’s the most widely accepted currency around the world and easy to change.

When I decided to see if it was possible to visit the Maldives on a budget back in 2014, information was so sparse that I couldn’t even find a photo of the islands I’d decided to visit. Well, that trip was one of my highlights of the past eight years and I’m so glad I went, despite not being able to find any information online. And the advantage to that lack of information was getting to be the only tourist on an entire island — I had the whole beach to myself ! If you know it’s safe to travel somewhere, but can’t find out much else, go for it. It’s probably far easier to get there than you think. And if not, it makes for a good story.

I’m definitely testament to that ! But expecting everything to go perfectly on your trip is only setting yourself up to fail. Nobody goes travelling and comes back without any stories of mishaps. No matter how prepared you are, at some point you’re going to get lost, get scammed, miss your bus, get food poisoning, injure yourself… the list is endless ! Expect it to happen, and don’t beat yourself up when it does. In a month’s time, you’ll find it funny rather than frustrating.

It achieves absolutely nothing and makes you look like an asshole. Instead, calm down, put a smile on your face, think of how this will make a great story one day, and rationally figure out an option plan. This too shall pass.

What happens if you arrive in a city, go to grab your fax confirmation for your accommodation, and your phone and laptop are out of battery ? I always make sure I have a hard copy of my guesthouse name and their address, as well as directions if I won’t be taking a taxi. Once I arrive, I’ll grab one of the hotel’s cards, so I’ll always know where I’m staying, and can show it to locals to ask for help with finding my way back.

So many people will tell you not to travel with pantalons, but if you wear jeans all the time at home, you’ll want to wear them while travelling, too. I didn’t start travelling with pantalons until my second year of travel, and man, I missed them so much ! They’re not *that* bulky so you really don’t need to worry about the extra space and weight. And in many cities in Europe, you’ll want to wear pantalons to fit in with the locals — you don’t want to look like a grubby backpacker in Paris !

Checking out is when you’re most likely to lose something. Whenever I check out of a place, I check the bathroom, I check under the beds, I check the desks, and then I make sure I have my passport, laptop, camera, money, phone, and external drive. I’ll be fine if I leave anything else behind. Having a routine that you go through every solo time will help you keep track of everything. I learned my lesson with this one when I left my passport behind in a guesthouse in Bagan, then left it in an apartment in London two months later.

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