Best Things to Do in Downtown Kingston: Cruises, Trolley Tours & Local Attractions
By Rosalyn Gambhir
Published: May 27, 2026
There’s a certain kind of charm in living in a city that still feels like it has more to show you.
As someone who now calls Kingston home, I’ve started to realize how easy it is to overlook what’s right in front of us. We get used to beauty when it becomes familiar.
Kingston has always been that place for me - familiar, yes, but never fully finished revealing itself. Between its waterfront views, layered history, limestone buildings, foodie scene and vibrant downtown core, it’s easy to forget just how much is packed into one city until you slow down enough to actually experience it.
That’s where “The Staycationer” mindset comes in for me - choosing to be a tourist in your own city, stepping into curiosity and experiencing your surroundings like you’re visiting for the first time.
And recently, I got to do exactly that, rediscovering Kingston with Kingston Destination Group visitor offerings at the gateway of the 1000 Islands and the UNESCO-designated Rideau Canal, from daily sightseeing cruises and complete dining cruises with Kingston 1000 Islands Cruises, to historic tours of the city with Kingston Trolley Tours, visiting local museums and attractions with K-Pass, and so much more.
And honestly? It felt like falling in love with the city all over again.
Cruising the 1000 Islands with a Sunset Cruise
If you’ve only seen Kingston from land, you’re missing half the story. Stepping aboard a cruise with Kingston 1000 Islands Cruises was one of those moments that makes you pause and fully take in where you are.
On board the glass-topped Island Star, the Sunset Dinner Cruise was a scenic journey of 3-hours with changing scenery through the heart of the 1000 Islands. A three-course meal is served at your table with live music and live-hosted commentary about the region as you sail past cottage islands and grand estates. You’ll be left in awe. Relax inside with panoramic views, or head out onto the open-air top deck as the sun sets and the sky gives you a show of its own. My partner and I enjoyed a side of Kingston we hadn’t done together in years.
It’s the kind of moment that makes you realize how much history and quiet beauty exist just beyond the shorelines of downtown Kingston.
While the Sunset Dinner Cruise was my personal experience, there’s a full lineup of cruises that each reveal a different side of the 1000 Islands and Kingston waterfront:
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Islands Brunch & Lunch Cruise: Enjoy a daytime 3-hour dining experience onboard the Island Queen as you wind through the 1000 Islands with a plated three-course meal served onboard with panoramic deck.
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Sunset Cocktail Cruise: Set sail on a 2-hour cruise along Kingston’s historic waterfront with a live host and curated music. Enjoy a selection of beer, wine, and cocktails as the sun sets. It’s a laid-back 19+ experience, perfect for an evening where the city itself is the entertainment
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Shipwreck Cruise: Created in partnership with the Great Lakes Museum, this cruise dives into Kingston’s maritime past while passing over historic waters, paired with artifacts and wreck-diving footage, bringing the region’s underwater history to life.
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Heart of the Islands Cruise: A 3-hour sightseeing cruise through the 1000 Islands featuring live-hosted commentary, a licensed bar and canteen, plus both indoor seating and open-air viewing decks.
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Discovery Cruise: A 1-hour tour where you get a front row seat in seeing historic Kingston landmarks such as Fort Henry, Royal Military College of Canada and the walls of Kingston Penitentiary from the waters.
Exploring Kingston by Trolley
If the water shows you Kingston’s beauty, the trolley shows you its personality.
My time exploring with Kingston Trolley Tours was shared with my mum and my partner, and it ended up being one of those unexpectedly perfect slow travel days - no rush, no agenda, just exploring and enjoying the sights, the stories and company. There’s something special about rediscovering a place together and sharing those “I didn’t know that!” or “wow!” moments in real time.
We hopped onto the iconic red trolley for the Hop-On Hop-Off Tour, winding through nine stops across the city. From the historic downtown core along Princess St to Fort Henry and the Kingston Penitentiary area, it’s a loop that makes you realize just how walkable and layered downtown Kingston really is.
What I loved most was the flexibility. You can stay onboard for the full 75-minute guided tour, listening to stories of Kingston’s past as the trolley moves through the city streets or hop off at any stop to explore museums, historic landmarks and waterfront spaces at your own pace. It makes the city feel accessible in a way that’s both structured and spontaneous at the same time.
If you’re short on time, the City Tour with no stops is perfect to explore Canada’s first Capital City! And then there’s the Ghost & Mystery Trolley Tour, a 90-minute evening ride through Kingston’s darker corners and haunted history, which adds a completely different atmosphere to the city. It’s eerie in the best way, it takes you off the beaten path to notable sites and notorious neighbourhoods that played a ghostly role in Kingston’s early history.
Take a Piece of Kingston Home with You
To kick off the adventures and in between exploring, right in the heart of downtown, steps from City Hall and Market Square, is the Waterfront Gifts & Apparel. This is where you can pick up your tickets, build your itinerary with the aid of the knowledgable staff onsite and browse around for a souvenir - it’s filled with locally inspired gifts and Canadian-made apparel. This shop lets you bring a small memory of the experience back with you.
The K-Pass: Your All-in-One Pass to the City
What stands out the most after exploring Kingston is how much is here - often right in front of us. Waterfront views. Historic landmarks. Immersive storytelling. Local culture. Museums. Cruises. Trolley tours. Walkable downtown streets. More restaurants per capita in Canada.
And when you bring it all together through something like the K-Pass, it becomes an easy, all-in-one way to experience the city differently, whether you’re here for a weekend, hosting guests or simply trying to rediscover your own city. It’s designed to make exploring effortless.
One pass, one price and suddenly Kingston opens up in a completely new way.
With 24, 48, or 72-hour options, the K-Pass bundles together some of Kingston’s best attractions, from sightseeing cruises and hop-on hop-off trolley access to museums, haunted walks, and special attractions like Fort Henry and Kingston Pen Tours.
It includes:
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A Kingston 1000 Islands Cruise (your choice of experience)
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Hop-On Hop-Off Trolley access
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16+ museums, tours, and attractions
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Bonus discounts at local dining spots and businesses
For me, the appeal is simple. It removes the friction of planning and replaces it with curiosity.
You don’t have to choose just one side of Kingston. You get to experience almost all of it. And when you consider the savings compared to individual tickets, it becomes not just an experience pass, but a smart way to explore Kingston.
The truth is, we often think of experiences as something we have to travel for. But Kingston quietly challenges that idea. The moment you slow down, stay curious and experience Kingston intentionally, the city shifts from familiar to fascinating.
Rosalyn Gambhir
I’m a daydreamer, a foodie, an adventurer, and an explorer. But most of all, a tourist in my own backyard of the limestone city rediscovering old favourites and hidden gems. As a proud Kingstonian for over a decade and an alumna of Queen's University, I has thrived in this vibrant community, which has fueled her creativity and passion for building a strong online community and supporting local businesses through my blogging, social media and freelance writing.
