If you haven’t heard of Guess Where Trips by now, I am thrilled to be the one to introduce you to these kickass surprise trips. It is not hyperbole when I say they are the best surprise day trips in Canada. I’ve been on 4 so far (including “The Waterfall Route” in Ontario, which I created!) and have another 4 at home waiting for sunnier days – although these trips are great for all seasons. There’s a discount below for you, so keep reading!

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What is Guess Where Trips?

Alright, you’re thinking, she’s hyping these day trips up, but what’s the deal? Well, thanks to owner and founder Jessica Off’s own humongous Ontario bucket list and creativity, the spark for Guess Where Trips started a few short years ago. Her travel wish list was a varied combination of hikes, hidden gems, foodie destinations, and odd attractions to explore. The first itinerary was actually a Christmas gift for family who loved them. Shortly after creating these homemade itineraries, the company Guess Where Trips was born.

Open Your Guess Where Trips Envelope

How Do Guess Where Trips Work?

When you visit the Guess Where Trips website you’ll notice a few things: 1) trips are now offered across Canada and in the USA, and 2) there are very little itinerary details available. This is the brilliance of these trips. If that’s confusing, hang on for a second. The first step is choosing your starting point. For example, if you’re in Ontario then you can choose Toronto, London, Ottawa, etc… as starting points. For Manitoba, start with Winnipeg, for Alberta there’s Calgary, in British Columbia it’s Vancouver, and in Nova Scotia start from Halifax. (I anticipate more locations and provinces will be added in the future.) Next, either choose a trip based on a theme, found in trip titles like “Funky Florals and Fine Wine” or “The Butter Tart Trail”, or take the Trip Quiz to see which routes best suite you, or (my favourite) close your eyes and point to one! I can honestly say that whichever trip you choose, and however you make the decision, you will have the best time discovering new places in Canada.

Tasty Treats on Surprise Day Trips in Canada

After making your purchase with discount code “TMC10”, choose between a PDF itinerary or a mailed physical copy, you’ll receive several envelopes – 1 per stop and an additional “Before You Go” envelope. The night or day before you go, open your “Before You Go” envelope. Without giving away any of the surprises for the next day, it will let you know when to leave the next day, any covid information to note, and what to bring for the day. It also includes information on the trip creator (check out the Ontario “Waterfall Route” for someone you might recognize!), pet, accessibility, and nutrition information, as well as any options for overnight accommodation and how long the trip may take. The morning of your trip, open up your first envelope and buckle up for a fantastic day!

Your First Stop Envelope for Guess Where Trips

What Should You Bring?

Some things you might want to bring include layers of clothing to match the weather, a reusable water bottle, cash and cards to pay for treats and souvenirs, comfortable shoes, a camera and/or phone, charging cables, hand sanitizer and a face mask, a solid playlist of road trip music or podcasts, a full tank of gas, and the rest of your Guess Where Trips envelopes! (Even the chronic overpackers will be able to pack light on these trips.)

What Can You Expect?

Each trip is specially curated by travel bloggers like yours truly who research, visit, and vet each destination. There are also special offers for Guess Where Trip travellers at some of the stops. The itineraries provide multiple options along the way to allow for a bit of a create-your-own-adventure experience as well. All in all, you can expect to create some great memories, discover new places, and have stories to share at the end of the day of your adventures.

Amazing Views on Guess Where Trips

Guess Where Trips Locations

As of December 2021, Guess Where Trips itineraries are available across the country from Halifax to Vancouver. Whether you want to explore your own province, gift someone who lives in another city, or travel your country with a few surprises sprinkled along the way, it’s currently possible in 5 provinces.

A very special part of each trip’s destinations is the local businesses that have been selected for you to visit. Every restaurant, cafe, ice cream shop, boutique, and store is run by small business owners who pour their heart and soul into their shops. As a small business owner myself, I appreciate the value these trips place on supporting local economies and the individuals behind them. It’s another reason why the chosen stops are so special and memorable.

There are many outdoor, cultural, and historical locations as well. The stunning views, friendly people you may meet, and fun facts you’ll learn along the way will surely give you the travel itch to discover more in your backyard.

Enjoy ice cream on your Guess Where Trip

My Guess Where Trips Review

You can probably guess by now that I’ve thoroughly enjoyed the trips I’ve taken with Guess Where Trips. I’ve travelled with family, my partner, and solo, and each time it’s been fantastic. To date, I’ve gone on the “Weird and Wonderful”, “Vistas, Falls, and Caves”, and “Historic Haunts”, and created the Ontario “Waterfall Route” itineraries. I’m a bit of a slowpoke and always take longer than recommended at a stop so technically I’ve got a couple of things to return to for each tour…but I kind-of love that too! Anytime you travel I think it’s great to have something to return to. It doesn’t matter if you finish your itinerary in one day because it’s in your possession once it’s purchased. For me, this only adds to the value of an already awesome experience.

The Guess Where Trip Waterfall Route

In addition to loving the surprise component, the snail mail itineraries, and the support for small businesses, another aspect of this company and these trips that I really appreciate is the focus on sustainable and responsible travel. In the past, Guess Where Trips has encouraged their travellers to clean up the places they visit and share a picture of it to social media in hopes that these actions will inspire others to help preserve and respect destinations for future visitors too.

Run into Chad Michael Murray on your Guess Where Trip

And last, you never know what extra surprises might be in store for you anytime you hit the road. I will never forget my first Guess Where Trip when I wound up accidentally walking through the set of One Tree Hill’s own Chad Michael Murray filming a holiday Hallmark movie in Bracebridge. University me would have lost her sh*t with excitement! (Okay, let’s be real, “adult” me was still pretty jazzed.) While I will probably never watch “Tycoon’s Kiss”, or any other cringy Hallmark rom-com, I will most definitely smile every time I think about sharing a sidewalk with one of the ballin’ Scott brothers!

Which Surprise Day Trips in Canada Am I Going on Next?

Sitting next to my computer at my desk are the next 4 trips I’ll be taking with Guess Where Trips. There’s “Funky Florals & Fine Wine”, “Outdoor Adventures & Scenic Roads”, “Bridges to Beaches”, and the scrumptious “Butter Tart Trail”. Which trips have you got your eye on?

About TMc


Me having a seat in front of one of the famous Brighton Bathing Boxes in Australia!

Heya! I’m Tara (Tar-ah)! Welcome to Travel with TMc where you’ll find quirky language tidbits, travel hacks for Canadians, and stories from the road. I hope you enjoy!
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2 Comments. Leave new

  • Jeannie Baker
    August 31, 2022 8:31 PM

    I cant seem to locate where i would look at the cost and trips available in Ontario and Alberta.

    • Hi Jeannie! Thanks for reading my blog post on Guess Where Trips. If you visit the “Trips” tab on the Guess Where Trips website and then scroll down and select the location you’re looking for, the price will be available for you there. Happy travels!


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