The Ultimate Kingston Ontario Weekend Itinerary

Written By: The Planet D

When planning an Ontario staycation, Kingston should definitely be on your list.

Located just three hours from both Toronto and Montreal, a mere 90 minutes from Ottawa, and conveniently located on Highway 401, Kingston, Ontario has everything you could possibly hope for in a staycation. The former capital city of Canada is home to a UNESCO World Heritage Site, five national historic sites, four Rembrandt paintings, and more restaurants per capita than most cities in Canada. Kingston has something for everyone.

Kingston Itinerary – 3 Perfect Days

kingston itinerary weekend getaway
Kingston’s #1 Tourist attraction – Read on to find out what it is!

We’ve put together the ultimate itinerary to help you plan your trip to Kingston. If you are looking to make the most of the long weekend, follow this guide and create the perfect weekend getaway in Ontario. For more information on Kingston Travel, visit the Kingston Tourism Website.

Where to Stay in Kingston

kingston itinerary 3 days
Secret Garden Inn

Secret Garden Inn is a beautiful boutique manor home. It is such an iconic Victorian Inn that they even mention it on the Kingston trolley tour! Located within walking distance from the waterfront, Princess Street, and many of Kingston’s top attractions it is a great choice to stay and the breakfasts are delicious. Visit their website for reservations and availability.

Day 1 Kingston – Downtown

3 days in kingston ontario

Day one of Kingston is all about being introduced to Kingston’s top attractions. Make your way downtown to explore the highlights of the city and get acquainted with the history and top attractions in Kingston.

Trolley Tour

kingston sign

Start your trip on the Kingston Trolley tour. This one-hour guided tour starts in historic downtown Kingston and takes you on a journey through Kingston’s history its top attractions. Your entertaining guide keeps the trip moving along as they offer information about the city’s history and insider tips. The tour makes stops at different points of interest around Kingston including Fort Henry, the Kingston Pen, The shopping district and Queen’s University. The Kingston Trolley Tour provides the perfect introduction to the city. Visit the City Trolley Tours to get your tickets – $28 for a one-hour guided tour

Kingston Visitor Information Centre

kingston ontario visitor center

At the end of your tour the Trolley lets you off at the Kingston Visitor Information Centre in front of City Hall and at Confederation Park. This is the perfect place to explore next. From the Kingston Trolley, you can pop into the visitor centre to get information about the attractions that interest you the most. Here are some of our suggestions for sights to fill in your first day in Kingston.

Engine 1051

kingston train engine 1051

Grab a snapshot in front of the Kingston Sign and then walk behind it to check out Engine 1051. Engine 1051 has been resting at this location for 40 years reminding visitors and residents that this area was once a bustling train yard. It’s beautifully restored and makes for one of best photo opportunities in Kingston.

Confederation Park

confederation park kingston ontario

From here, you can take a stroll along the waterfront for different views of City Hall, the waterfront, and the fountain. As you make your way down to the yacht club, make sure to keep an eye out for the Martello Tower that stands in the center of the Marina. This is one of six Martello Towers in Kingston. You can’t tour this one, but there are others that you can go inside. The Murney Tower is a 15-minute walk from Confederation Park along the waterfront, and Fort Frederick Tower, which is free to visit, is located the Royal Military College.

Spend as long as you like exploring the waterfront, it is 8km long with many places to see including the Marine Museum and the PumpHouse Museum. Don’t forget to stop to take in the beautiful waterfront views.

Lunch on the Patio at Olivea Fine Dining

deb eating lunch on a patio in kingston ontario

Now that you have worked up an appetite, grab lunch on a patio on Brock Street. Located just a two-minute walk from the Visitor Information Centre, Olivea Fine Dining has excellent Italian cuisine. In fact, each year the staff travels to Italy to immerse in the Italian culture for inspiration and information on the Italian cuisine and recipes. The food is delicious and it is located across the street from City Hall and the square which is home to Canada’s oldest public market. Make reservations at Olivea Fine Dining.

Springer Market Square

kingston ontario city hall

This square feels like you have stepped back in time as it is surrounded by historic buildings. The architecture is so authentic, it has been used in movies and TV shows that are set in the 1700s and 1800s. Most recently Murdoch Mysteries filmed one of their episodes in the square. 

Explore Kingston’s Historic Downtown

downtown kingston ontario princess street

To work off some of that food, it is time to explore downtown Kingston. There is so much more to the city than just Princess and Ontario Streets. Start at Kingston City Hall. This National Historic Site is a beautiful 19th-century Neo-classical building that is the centrepiece of Kingston’s skyline. You can book tours to go inside. (Check COVID regulations as at the time of writing, tours were put on hold)

Kingston’s Alleyways

rochleau court sign kingston ontario canada

From here it’s time to explore two iconic alleyways in Kingston. Walk just two minutes around the corner and you’ll find Rocheleau Court. It has restaurants, shops, and courtyards that are simply gorgeous. Plus, here you’ll find one of Kingston’s most popular restaurants, Chez Piggy. This back alley is a lovely stroll through a maze of courtyards, patios, restaurants, and shops.

Martello Alley

martello alley kingston itinerary

Another must-visit alley in Kingston is Martello Alley. Located on Wellington Street this short walk from Rocheleau Court takes you to Martello Alley. This historic alley is one of Kingston’s hidden gems. The colourful courtyard is filled with original artwork created by a community of artists. The alley was inspired by La Rue du Trésor in Québec city and the staff is friendly and welcoming. Go inside and grab a piece of memorabilia and say hello to the artists. See what’s going on in Martello Alley

Walking Tour with Arthur Milnes

A walking tour with Arthur Milnes is one of the most unique things to do in Kingston and is a great way to spend an hour before dinner. Meeting at the Visitor Information Centre, this tour takes you from the waterfront through downtown. Arthur is a local historian who shares many personal stories from life in the city. Taking a tour with him will give you insider tips of where to eat and what to do but it is the personal stories that we enjoyed most. Arthur hosted President Jimmy Carter at his house when he visited Kingston to receive an award. He was also a speechwriter for Prime Minister Harper so he has plenty of stories to tell. Visit Arthur Milnes Walking Tours to book a tour.

Dinner at Wooden Heads

food in kingston ontario restaurants

There are so many places to eat in Kingston, it can be overwhelming to choose. Arthur Milnes has some great suggestions, but if you want one of ours, we loved the atmosphere and food at Wooden Heads. Wooden Heads is known for its gourmet wood oven pizzas and we can attest that it was delicious. But they also have pasta and Italian food on the menu as well to suit anyone’s taste. See their website for reservations.

Drinks at Musiikki Cafe & Whiskey Bar

musiikii cafe kingston patio

No trip to Kingston would be complete without going to see live music and Musiikii Cafe & Whiskey Bar has a fantastic atmosphere and exceptional cocktails. The backyard outdoor setting is a relaxing venue to listen to local artists. What sets Musiikki apart is its selection of whiskeys. From scotch and bourbon to Canadian Rye, you must try one of their whiskey cocktails, but we warned, they can be pricey.

Visit the Musiikii Cafe website for the music lineup and menu. It is also a fair-trade coffee shop during the day.

Day 2 in Kingston – Art and Academics

Isabel Bader Kingston Ontario

After a delicious breakfast at the Secret Garden Inn, it’s time to set out for day two of your Kingston itinerary. You can walk to everything, but if you want to make the most of your time, you can call an uber, or chances are you are probably on a road trip, so hop in your car and head to Queen’s University campus.

Queen’s University Campus

queens university campus kingston

Today is a beautiful day to explore Kingston’s historic architecture. There is no better place to stroll through the historic buildings of Kingston than Queen’s University dating back to 1831.

Agnes Etherington Art Centre

agnes etherington kingston ontario

While you are walking through the campus, be sure to stop at the Agnes Etherington Art Centre to see four of Rembrandt’s works of art. This art gallery is free to visit (donations welcome) and was one of our favorite places to visit in Kingston. The gallery not only houses traditional and historical art, but it also has contemporary, Indigenous, African, and regional art. It really is something we highly recommend to do when visiting Kingston. See the website for exhibits and opening times.

Lunch and Afternoon – River Cruise

river cruise on the st laurence from kingston ontario - thousand islands

After a morning on land, it is time to hop aboard the Island Queen for the Heart of the Islands cruise. This three-hour lunch cruise takes you onto the St. Lawrence River where you’ll explore the world-famous Thousand Islands. The Thousand Islands actually consist of 1800 islands and islets that line the St. Lawrence River along the Canada – U.S. border. You’ll see Fort Henry, the Martello towers of Kingston, and the Kingston skyline as you enjoy a three-course lunch. Make sure to upgrade to a window seat for a premium view of the Thousand Islands. You are free to roam around on the cruise so no matter where you are sitting, you’ll have a good view.

Murney Tower National Historic Site

murney tower kingston canada

It’s already been a full day, but if you want to take a stroll, Murney Tower is one of the two Martello Towers that you can tour in Kingston. It is a 15-minute walk from Confederation Park (where you’ll be disembarking from the cruise) and it’s a great way to work up an appetite before dinner after sitting for three hours on the boat. This is a beautiful Martello tower and even if you don’t tour inside, you must at least take a walk around to see it from all angles. Visit the Murney Tower Website for hours.

On your way, you can stop to see the Pumphouse Museum which was home to Kingston’s first waterworks from 1851 to 1952. Check it out here.

Dinner – Union Kitchen and Cocktails

union cafe princess street kingston

Once you have finished taking your tour through historic sites make your way to Princess Street for dinner at Union Kitchen and cocktails. This cocktail lounge has a chic urban vibe serving fantastic food. Make sure to order the steak frites, our personal favourite. Make reservations for Union Kitchen here.

Drinks and Arcade Games at Barcadia

barcadia sign kingston ontario itinerary

For something different after dark, make your way to Barcadia. This beer hall has classic video arcade games to take you back to your youth. But since you are no longer a teenager, you can enjoy a beer or cocktail as you play your favourite arcade game. Check out Barcadia for more details.

Day 3 – History and Heritage

Kingston Mills Locks

best things to do in kingston ontario video

A visit to Kingston would not be complete without visiting the UNESCO World Heritage Site of the Rideau Canal. Located just outside of town are the picturesque Kingston Mills Locks. This set of four locks was the location of the first mill on the Rideau Canal dating back to 1784. You will need to drive out here, but it is worth seeing this feat of engineering. If you time it right, you may see a boat going through the locks. Check out: Amazing Rideau Canal Cruise – A Unique Cruise Holiday with Le Boat

Morning tour of Kingston Penitentiary

kingston penitentiary lookout tower

It’s the number one attraction in Kingston, so you cannot miss visiting the notorious Kingston Penitentiary. There are different tours offered from 60-90 minutes. The Kingston Pen closed in 2013, but today you can go inside to see where some of Canada’s worst offenders were incarcerated. Across the street is the former Women’s prison. There are different tours from the standard tour to the extended and architectural tours. A Hollywood movie was filming while we were there. Kingston Pen movie tours are offered as well. Pick your tour here.

Lunch at Juniper Cafe

modern architecture in kingston waterfront

Located on the waterfront the Juniper Cafe has one of the best settings for lunch in Kingston. It is located between Tett Centre for Creativity and Learning and The Isabel Bader Centre for the Performing Arts. This area is a beautiful blend of historic buildings and modern architecture. Make sure to take a walk through the Tett to see the artisans at work. Check out the Juniper Cafe for more information.

Make Your Way to Fort Henry

fort henry walls kingston ontario

After lunch, a visit to yet another national historic site is a must. Fort Henry also has one of the best views of Kingston and is a great place to watch the sun set over the city. Fort Henry was built during the War of 1812 due to its strategic location. As Canada’s first capital city, Kingston was expected to be a target in the war but luckily it was never invaded and the fort is in excellent condition after its restoration in 1936. It is now one of the top attractions in Kingston to learn about Canada’s military history. Visit the website for opening hours and exhibits.

On Your Way Home Bonus…

daft brewery kingston ontario

Kingston has a long history of brewing beer dating back to 1790. In fact, Kingston even has ties to Canada’s oldest brewery, Molson, when the son of John Molson moved to Kingston to start his own brewery and distillery in 1824. Today Kingston has eight breweries and one cidery and a very cool one to visit is the Daft Brewing Company. It feels like a little slice of Key West, situated in a renovated five-car garage. Make sure to order a flight and to sample their very unique flavors and then pick up a six-pack to enjoy once you are home from your extended weekend getaway. Visit Daft Brewery for details

There are so many things to do in Kingston that a long weekend in the city is barely enough time to scratch the surface, but if you plan it right, you’ll be able to see a lot in a short time. Kingston is truly a surprising city, it has come a long way since it was Canada’s first capital and if you plan a getaway you won’t be disappointed.

Travel Planning Resources

Looking to book your next trip? Why not use these resources that are tried and tested by yours truly.

Flights: Start planning your trip by finding the best flight deals on Skyscanner

Book your Hotel: Find the best prices on hotels with these two providers. If you are located in Europe use and if you are anywhere else use TripAdvisor

Find Apartment Rentals: You will find the cheapest prices on apartment rentals with VRBO

Travel Insurance: Don't leave home without it. Here is what we recommend:

  • World Nomads - Digital Nomads or Frequent Travelers.
  • Allianz - Occasional Travelers.
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Need more help planning your trip? Make sure to check out our Resources Page where we highlight all the great companies that we trust when we are traveling.

About The Planet D

Dave Bouskill and Debra Corbeil are the owners and founders of The Planet D. After traveling to 115 countries, on all 7 continents over the past 13 years they have become one of the foremost experts in travel. Being recognized as top travel bloggers and influencers by the likes of Forbes Magazine, the Society of American Travel Writers and USA Today has allowed them to become leaders in their field.

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