Kingston has it all; which is exactly why after finishing my studies at St Lawrence College, I haven’t left! There’s always something new to do and after being here for over 7 years, there’s still so much of this city I have yet to explore. In fact, Kingston has been ranked #8 for the best place to live in Canada by Millenials!

Not only a great place to live and work, but also an ideal place for a romantic getaway, girls trip, or a family vacation. This itinerary will help you create the perfect day in Kingston.

Grab Some Breakfast At Toast & Jam

We have a lot of ground to cover so you need to start your day by fueling up. Start with breakfast at Toast & Jam, a modern and cozy restaurant located on the west end. This is a busy spot on the weekends, with wait times at 20 mins but trust me, it’s worth it! You’ll quickly understand why once you try their brunch masterpieces. While waiting, I usually pop next door to the sister company, Bread + Butter and grab some delicious baked goods for the car ride or to eat while waiting for a table. No judgement.

Must Try: Southern Cornbread Breakfast $14 – Bacon, Cheddar, Jalapeno Cornbread topped with caramelized onions, poached eggs, and red pepper sauce.

Hike at Lemoine’s Point

After breakfast, work off those calories with a hike at Lemoine’s Point. There are many different trails offered depending on the length you would like. This is also a great spot to practice your photography skills. When you go, make sure to bring seeds as you will be able to feed the chickadees from your hands. Best of all enjoying this natural beauty is free.

During the most recent time that I went, we were chased down by some wild turkeys that were fed by other humans. These turkeys literally came out of nowhere and had us circled. Moral of the story, do not feed wild turkeys!

Visit The Chit Chat Cafe

Of course, you’ll need some caffeine to keep you going throughout the day. The Chit Chat Cafe is a coffee shop with a great sense of community. Here, you will strike up a conversation with either the barista or one of the locals, while enjoying a delicious cup of their java. If you’re like me and the bitterness of coffee throws you off, there’s a wide selection of flavoured coffees. They also offer the option of purchasing a bag of their beans to take home (available in over 10 different flavours.)

Wander Around Martello Alley

Next up, head downtown to one of Kingston’s oldest stone alleys and view some beautiful local artwork at Martello Alley. Make your way down the bright and vibrant alley and feel as though you have been transported to La Rue du Tresor in Quebec. Continue towards the back where you’ll reach their indoor art gallery that features displays, photographs of iconic places in Kingston, and artisan jewellery. There’s always the chance that one of the artists will be there too!

Have Lunch At Sally’s Roti Shop

Next door to Martello Alley is Sally’s Roti Shop. This is a super casual eatery where you can stuff your face with doubles, rotis, jerk chicken, and oxtail plates. With the owners coming from Trinidad and sharing their Caribbean influences, you’ll get authentic homestyle cooking at very fair prices. My partner and I usually share a roti because they’re so massive! They also have a beautiful mural which makes for a great opportunity to snap a photo for Instagram.

Must Try: Goat Curry Roti $11.50. They also have vegetarian options available.

No doubt, there’s an incredible foodie scene here in Kingston. Sometimes it can be a bit overwhelming on deciding where to eat. A Kingston experience that should be on everyone’s bucket list is Kingston Food Tours. These guided tours allow you to taste a sample of some of the best restaurants in while learning about the historic culture and thriving community.

Tour City Hall

Confession time, I have lived in Kingston for 7 years, but have never taken a tour inside City Hall despite it being open to the public. This is the most iconic building on Kingston’s waterfront since 1844, and has probably been photographed an absurd amount of times.

The free self-guided tour has two floors available year-round and will take you about 30 mins to complete. If you’re here in the summer, take the guided tour where you get to tour the cell blocks. I would highly recommend stepping inside for all of the beautiful design elements and learning about Kingston’s history. Having the opportunity to travel through Kingston like a tourist opened my eyes to a lot that is offered.

At this point, you might be ready to head over to your ‘home away from home’ for a quick recharge. Here are a few places I would recommend.

The Green Acres Inn – Located on the West End of Kingston
The Delta Hotel– Downtown on the waterfront
Hochelaga Inn – Downtown

Carb Up On Pasta at Olivea

Nothing is as satisfying than a big bowl of saucy pasta when you’re hungry. If you want authentic Italian food but can’t afford a vacation to Italy, then this is the place for you. Great service and mouth-watering cuisine. Olivea is modelled after a traditional Italian trattoria and can easily prove how Italian food is one of the best cuisines in the world! Salute!

Must Try: Tagliatelle Bolognese $21
Bonus: Olivea is one of the restaurants that are toured during a Kingston Food Tour.

Sip On Some Prestige Bourbon At Musiikki Cafe

If you take pride in your alcohol, Musiikki Cafe is a great place to have a post-dinner beverage. They have an impressive selection of scotch and bourbon plus an ultra laid back setting. This intimate whiskey bar offers live music every night of the week and is a great place to hang out.

Speaking of music, if you have heard of The Tragically Hip and The Glorious Sons, then you know that Kingston produces some incredibly talented musicians. Take the night to explore the downtown bars to find your next favourite artist! We have listed some spots to check out in the Google Map below.

While you’re enjoying your entertainment for the evening, stop by Ontario’s oldest brewpub: Kingston Brewing Company for a frosty pint. If you’re not into the live music scene, Kingston also has its very own independent movie theatre located downtown. The Screening Room specializes in contemporary independent, foreign & art films.

Late Night Munchies At Bubbas

Where do I even start to explain why you must finish your night with this Kingston staple. It’s known as “The Best Damn Poutine in Kingston.” Ask anyone who has ever had a night out here and they will tell you how they have ended up at Bubba’s at least once. They’re known for their poutine, it’s what they do and they do it oh so well. It’s the kind of poutine that doesn’t try too hard but still tastes unreal. With two locations downtown, it’s the ultimate spot for both locals and visitors.

Must Try: Quebec Style Poutine $7.95 – French fries and curd cheese smothered in gravy. Local tip, add chicken AND bacon to your order.

Make The Most Of Your Visit To Kingston

I hope this itinerary helped you get started on planning your next trip to Kingston! If you’re looking for more things to do, check out our blog post Things To Do This Winter In Kingston.