Kingston, Ontario, is a city that rewards curious explorers. Its well-preserved architecture, storied past, and scenic waterfront make it ideal for a variety of city tours. Whether you prefer a nostalgic trolley ride, a lively walking adventure, or an aerial perspective, Kingston offers memorable ways to see its historic streets and hidden corners.
Among our favorites is the Kingston Trolley City Tour—a charming way to cover a lot of ground fast while enjoying stories of Kingston’s 300-year history. We also love the Hidden Kingston City Walking Tours for a quirky, personal look at lesser-known tales and secret spots.
And for those who want a broader experience, the From Montreal: Kingston City Day Trip & 1000 Islands Cruise combines history with stunning river scenery.
If aerial views are your thing, the Kingston City Tour by Air offers a quick but breathtaking perspective on the area’s landmarks.
Each of these options appeals to different interests and time frames, making Kingston a city that’s as easy to explore as it is fun to discover.
Quick Overview
For a quick, fun introduction, the Kingston: Trolley City Tour (link) is a 1-hour ride on a nostalgic red trolley that covers Kingston’s downtown, Queen’s University, Fort Henry views, and Kingston Penitentiary. It’s perfect if you want a broad overview with a friendly guide.
If you prefer to walk and uncover stories on your own terms, the Hidden Kingston City Walking Tours (link) offers a 1.5-hour stroll focusing on funny, surprising, and lesser-known tales of the city’s past.
For a comprehensive day, the From Montreal: Kingston City Day Trip & 1000 Islands Cruise (link) combines a guided tour of historic sites with a scenic boat cruise on the Saint Lawrence River, ideal for travelers staying in Montreal or nearby.
And if a quick aerial overview sounds appealing, the Kingston City Tour (link) provides a 30-minute helicopter or plane ride giving sweeping views of Kingston’s waterfront, forts, and sunken ships.
1. Kingston: Trolley City Tour
Rated 4.6 out of 5 from nearly 100 reviews, the Kingston Trolley City Tour offers an engaging 1-hour trip through Kingston’s downtown core and shopping districts, aboard a nostalgic red trolley. This tour stands out for its lively storytelling, as guides share tales spanning over 300 years of Kingston’s past.
The route includes stops at Queen’s University to admire its classic architecture and Kingston Penitentiary, which once housed Canada’s most notorious inmates.
What makes this tour particularly appealing is the combination of historical insights and scenic views. You’ll get to see Fort Henry from Point Henry, which is a photographer’s favorite spot, especially during sunset.
The central boarding point makes it easy to hop on and off, and the small group size ensures a personalized experience. The guide’s expertise shines through as they connect Kingston’s past to its present, making history feel alive.
Priced at $32 per person, this tour offers excellent value for a quick yet rundown of Kingston’s main sights. It’s perfect for first-time visitors or those with limited time who want a spirited introduction to the city.
Bottom Line: If you enjoy a lively, story-driven tour and a chance to snap some scenic photos, the Kingston Trolley City Tour is a fun, affordable choice.
2. Hidden Kingston City Walking Tours
In just 1.5 hours, the Hidden Kingston City Walking Tours unveil Kingston’s quirky, lesser-known tales—perfect for travelers eager for a more personal and humorous perspective. Rated 5 out of 5 from four reviews, this tour prides itself on uncovering Kingston’s lighter side, from tales of duels and sea serpents to amusing incidents involving tricky tenants and musical mischief.
Led by engaging guides, this tour explores historic buildings, prestigious sites, and hidden corners that most visitors miss. Along the way, you’ll have plenty of opportunities to snap photos of architecture and landmarks, all while learning amusing stories and facts that make Kingston’s past come alive with humor and personality.
The tour starts and ends at convenient points downtown, making it easy to combine with a meal or a coffee break afterward. Priced at $28 per person, it provides a delightful, intimate experience that’s well suited for those who love storytelling and discovering the city’s offbeat side.
Bottom Line: If you enjoy exploring a city through quirky stories and hidden sights, this walking tour offers a memorable, light-hearted experience at an accessible price.
3. From Montreal: Kingston City Day Trip & 1000 Island Cruise
For around $122, the From Montreal: Kingston City Day Trip & 1000 Islands Cruise provides a full day of sightseeing, combining historic Kingston landmarks with a scenic cruise of the 1000 Islands. This guided tour takes care of transportation with hotel pickup and drop-off in central Montreal, making it a stress-free way to explore.
The tour’s highlights include visiting Kingston City Hall, an impressive 1844 building, and notable sites like the Royal Military College and Queen’s University. After a cultural stroll around downtown, you’ll board a boat for a cruise on the Saint Lawrence River, where you can admire historic mansions and natural scenery, including the famous sunken ships near Garden Island.
Guests appreciate the smooth logistics and the opportunity to see Kingston’s architecture and waterways in one day. The combination of a guided tour and leisure time to explore on your own at the end makes it a good pick for those wanting a balanced experience.
Bottom Line: Ideal for travelers who want a comprehensive day trip from Montreal, blending history and natural beauty with ease and comfort.
4. Kingston City Tour
At just 30 minutes, the Kingston City Tour by air is a quick, panoramic way to see Kingston’s top landmarks from above. Although the review scores are not listed, its unique offering makes it a standout. From an aerial perspective, you’ll fly over Kingston Harbour, Fort Henry, and the Kingston Penitentiary—giving a new dimension to your understanding of the city.
This tour also includes views of the Garden Islands shipwrecks, which are a fascinating sight for maritime enthusiasts. Its brevity makes it ideal for travelers short on time or for those who want a quick, impressive introduction to the city’s geography and key sites.
The experience is perfect for photography lovers or anyone curious about Kingston’s layout from above. The cost is higher at $236, reflecting the exclusive nature of aerial tours, but the perspectives gained are unmatched.
Bottom Line: If you’re after a quick, visually stunning overview of Kingston’s landmarks, this aerial tour makes for a memorable highlight.
How to Choose the Right Kingston Tour for You
Choosing between these options depends on your interests, schedule, and budget. If you’re all about history and storytelling, the Trolley City Tour offers a lively, comprehensive introduction. For a more intimate, humorous experience, the Hidden Kingston walking tour fits nicely, especially if you love uncovering stories on foot.
Budget-conscious travelers or those wanting a flexible day of sightseeing should consider the Montreal day trip with a cruise, which combines ease with rich experiences.
Meanwhile, if a bird’s-eye view excites you, the aerial Kingston City Tour provides breathtaking vistas in a short amount of time.
Book early, especially in the busy summer months. Many tours fill up quickly, and planning ahead ensures you get your preferred experience. Think about what kind of exploration suits your style—whether it’s walking, riding, or flying—that will make your Kingston visit truly memorable.
Final Thoughts
Kingston offers a variety of city tours that cater to different interests and time constraints. Whether you want to hop on a nostalgic trolley, wander through stories on foot, cruise the Saint Lawrence, or take to the skies, there’s an option for everyone. For most visitors, combining a trolley ride with a walking tour gives a well-rounded feel for the city’s character.
If you’re planning a trip, consider your schedule, budget, and curiosity level. The Kingston Trolley City Tour and the Hidden Kingston Walking Tour are excellent choices for a short visit, while the Montreal day trip appeals to those looking for a full day of varied experiences.
Don’t forget to book early, especially if you want to enjoy popular options during peak season. Kingston’s unique blend of history, humor, and scenic beauty makes it a city worth exploring in multiple ways.