Touring Historic Kingston, a 3-Day Family Guide


Before visiting Kingston, Ontario I have to admit, I didn’t know much about the city.  Located a 2.5 hour drive from Toronto and 2 hours from Ottawa, it’s a destination for many and after spending three days there with my family, I see why.  So if you’re planning to visit Kingston or perhaps it hasn’t even been on your radar yet, we’ve made it easy by laying out our entire itinerary, along with some tips we know you’ll find helpful before hitting the road!


Situated on the shores of the St. Lawrence River of Lake Ontario, the city was first established in the 1800’s and was actually named the first capital city of Canada, before being changed to Ottawa four years later. Kingston began as a military and train works centered town, and though trains are no longer constructed in Kingston, the Canadian Forces has remained a strong as part of Kingston’s identity today.


So, you might be wondering, is Kingston really a family-friendly destination?


Absolutely!  The city has a deep history that has been well-preserved and there are many ways your family can enjoy it. From walking and trolley tours, to cruise ship tours through the 1000 islands of the St. Lawrence River, there are opportunities for learning, exploring, sightseeing, and relaxing for each member of your family!


Highlights of our Trip
  • Watching the cruise ships arrive and depart from our balcony at  Holiday Inn Waterfront
  • Creating our own stone fired pizzas at Score Pizza
  • Meeting The Town Crier and going on a special walking tour with him
  • Riding the Trolley through Kingston
  • Visiting Fort Henry National Historic Site and Royal Military School of Canada
  • Strolling through Ontario’s oldest Farmers Market
  • Cruising through The 1000 Islands



Where to Stay
  • Holiday Inn Waterfront is located in the heart of Kingston and within a short walking distance of a long-list of tour opportunities, shops, restaurants, and of course the waterfront. This pet-friendly property is perfect for families with an indoor and outdoor (seasonal) pool, on-site restaurant, guest laundry, free WiFi, and plenty of parking.  One of our favorite parts of our stay here was the view from our balcony. Overlooking Crawford Warf into Kingston Harbour, we were not only able to watch the cruise boats arrive and depart, but we could take in a little bit of Kingston all in one view.



Where to Eat

Kingston is filled with choices and varieties of restaurants, most of them being locally owned and operated; here are three that we absolutely loved:

This unique pizza shop offers two ways to order, you can choose a Signature Pizza or build-your-own by choosing from a wide variety of toppings. All pizzas are stone fired to perfection and are so tasty! We ended up having Score Pizza for dinner two nights in a row because it’s just that good!

This popular bakery & restaurant was started to resolve a problem, original founders of the beloved Chez Piggy Restaurant, wanted to open a small bakery to provide hand-made bread that would  complement their restaurant’s menu. From that small seed, grew Pan Chancho Bakery & Cafe, a European style bakery, a gourmet food shop and a dine in cafe. We enjoyed a delicious breakfast including french toast for the kids and a salmon eggs Benedict for mom and dad!

This trendy restaurant is just steps from the waterfront and provides views of beautiful City Hall. The menus brings together flavours from the East Coast and Mexican BBQ to offer a variety of tasty comfort foods. We lucked out with the perfect patio weather and enjoyed the sunset while connecting over a delicious plate of fish tacos and traditional fish & chips, the tartar sauce is perfect!


Get The K- Pass

When you visit Kingston, do yourself a favour and grab a K-Pass! It’s an all-inclusive pass to the city, including 7 attractions, 8 restaurants, and several other offers and bonuses. You can choose an access pass for 24, 48, or 72 hours, which includes the 1000 Islands Cruise, Trolley Tour, and much more! With this pass, you won’t need to worry about ticketing, extras costs, bookings, or missing out on the best attractions the city has to offer!


Day 1  |  Arriving in Kingston and Amazing Local Pizza

We arrived into Kingston and were pleasantly surprised by the location of our hotel, jetting out onto the water, we were in the perfect spot to look out onto the harbour and within walking distance to everything we could possibly want or need. After five hours on the road, we got settled into our room at the Holiday Inn Waterfront, and then hit the town for some pizza!

Our friends at Visit Kingston recommended and gifted us with a meal at Score Pizza, and I’m so happy they did, otherwise we may never have discovered the best build-your-own-pizza place ever! (We loved it so much that we grabbed more for take out the following evening). The restaurant is conveniently located down town and only a 5 minute walk from the hotel, easy for little legs! To order your pizza, you can either choose a signature pie or build your own by choosing toppings as someone makes it right in front of you, similar to those popular sandwich shops. At the end, your pizza is put into a fire stove to give it that perfect crust! Next time you visit Kingston, please don’t forget to eat here!



Day 2  |  Meeting The Town Crier & Taking a Trolley Tour

Our day began with a bang, literally! A thunderstorm rolled into Kingston in the early morning and strong winds had stirred up choppy waters, and just about everything else!  We had a lunch cruise scheduled for the day, although because of the inclement weather, the cruise needed to be postponed. Luckily, there are several ways to tour the city of Kingston, and our first stop of the day was definitely one of our favorites!


Tip: We highly recommend stopping in the Visitor Experience Centre as one of the first things you do when you visit Kingston. With friendly staff, details and booking of tours, helpful literature, and locally made souvenirs, you can easily plan your visit!


The Visitor Experience Centre is located across from City Hall, the Kingston harbour, and of course our hotel. Here, we met with The Town Crier, authentically dressed and eager to share stories, tips, and a bit of a behind the scenes tour on Kingston.


We were so lucky to have a private walking tour with The Town Crier, an absolute expert on the area who has been making public announcements throughout the town for over 30 years! He’s a wealth of knowledge and someone we highly suggest meeting during your visit to Kingston! Keep in mind, he’s a bit of a celebrity, so you may want to grab a photo with him!



Following our walking tour of City Hall and surrounding streets, we hopped on a Kingston Trolley Tour! These hop-on, hop-off style tours follow a route throughout the city that includes tour sites such as Fort Henry National Historic Site and Canada’s Penitentiary Museum.


Tip: Make sure to grab your Passport booklet at the Visitors Experience Centre (where you board the trolley), because not only is it a guide for the tour (with descriptions of each stop, suggested time to spend at each, and any walking distances), but you can collect stamps as you go just like a real passport!



Tip: Designate at least half a day to for a Trolley Tour, there are so many places to visit!
The Trolley arrives and departs at each location every 30 minutes, so if you plan your time well, you can check out every tour!



Day 3  |  Exploring Ontario’s oldest Farmers’ Market, Cruising 1000 Islands, and Wandering Downtown “K Town”

Our first stop of the day was breakfast at Pan Chanco Bakery, a Kingston favorite and one stop shop for delicious home style baked breads, treats, and meals in their dining room. We settled in for a delicious meal of french toast for the kids and salmon eggs benedict for mom and dad – We highly recommend both!


Pan Chanco Bakery


Next up, was a stroll through Ontario’s oldest farmers market, The Kingston Public Market. Established in 1801, the city of Kingston didn’t have any stores in operation yet, so the market was the place where anyone looking to buy, sell or trade goods came to do business.  Today, the Public Market is still a hub of community and hosts a full list of vendors selling the highest quality local produce, prepared foods, garden plants and flowers, and handmade crafts.


The Kingston Public Market


Following a morning of local eats and crafted goods, we were ready to tour the beautiful 1000 Islands we had heard much about! There are a few different options for touring the islands. Initially, we were scheduled for a lunch cruise with a delicious menu, although the day we were to board a strong winded thunderstorm came through Kingston and all cruises were cancelled. Luckily, we were able to re-schedule for the following day (which was beautiful weather), and although the lunch option was sold out, we still got to take in the beautiful sights atop a 3-story ship resembling an old paddle boat.

The islands of the St. Lawrence River are a unique sight to see and gives us all the cozy cabin feels. Many of the islands have single property dwellings built right into them and are only reachable by boat.  The largest of the world renowned islands, “Wolf Island,” is a 29km long island reachable by ferry from Kingston, and would make for a perfect day trip!



After a three hour long cruise through the islands, we returned to Kingston and regained our land legs back in time for dinner and a stroll through “K-Town” (aka downtown Kingston).

Dinner at Dianne’s Fish Shack & Smokehouse was the perfect way to cap the day and our stay in Kingston, Ontario. We lucked out with beautiful weather giving us the opportunity to sit on the street-side patio, watch the sunset over the clock tower of City Hall, and watch the downtown buzz of people.  We delighted in a plate of fish tacos and traditional fish & chips, all were incredible!

Following our meal, we took a stroll through downtown Kingston to take in as much of the city as we could before we departed the next morning. We absolutely loved how walk-able this city is, especially with children.


Tip: If you’re worried about how far your little ones are capable of traveling on foot, bring along your stroller or collapsible wagon. Don’t bother driving to close by locations, walking is much easier!



Our view from dinner at Dianne’s Fish Shack & Smokehouse
Local shops across cobblestone Princess Street, Kingston

Night view of Crawford Warf, Kingston


We absolutely loved our visit to Kingston, Ontario and would recommend a trip for any family! With so much to learn, see, and do it’s a great place to immerse yourself in the culture of the city and learn about the heritage of Canada.


View of Kingston Marina and Martello Tower


Disclosure: We were generously hosted by Visit Kingston so that we could share this wonderful experience with you! As always, our opinions are entirely our own and the experiences we participated in align with our family lifestyle.


For more details and information, or for planning your trip to
Kingston, connect with our friends at Visit Kingston: