Uncover Kingston’s rich past through the landmarks, stories, and characters that shaped Canada. From fortifications and penitentiaries to medical discoveries and maritime heritage, Kingston offers you something old and something new around every corner.
Day 1:
Morning
Start your discovery at Fort Henry National Historic Site, a cornerstone of Kingston’s UNESCO World Heritage designation (shared with the Rideau Canal and fortifications network). Set above Lake Ontario, Fort Henry immerses groups in 19th-century garrison life with guided tours, artillery demonstrations, and seasonal programs like the Sunset Ceremony and Fort Fright. Winter visitors can enjoy scenic overlooks and heritage architecture that photograph beautifully in the snow.
Lunch
Take a break for lunch at Black Dog Tavern, where French-inspired bistro fare complements Kingston’s historic ambiance, or enjoy a casual meal featuring locally sourced ingredients at Harper’s Burger Bar, perfect for groups. For those seeking artisanal breads, sandwiches, and pastries, Pan Chancho Bakery & Café offers a cozy, historic setting in downtown Kingston. These options allow visitors to experience a variety of Kingston’s culinary flavours while staying immersed in the city’s character.
Afternoon
Continue to the Great Lakes Museum, where interactive galleries trace Kingston’s maritime story. Step aboard the S.S. Keewatin, a meticulously restored Edwardian passenger liner now permanently docked beside the museum. The ship’s staterooms, dining saloon, and engine room offer a rare window into early-1900s travel on the Great Lakes. The Great Lakes Museum is open year-round.
Dinner
Dine at AquaTerra, where refined regional cuisine pairs with lakeside views; Tango Nuevo, offering contemporary Canadian dishes with local ingredients; or Wharf & Feather, perfect for group-friendly private dining experiences. These dining options not only satisfy appetites but also continue the story of Kingston’s culinary evolution, blending historic surroundings with innovative flavours.
Evening
After dinner in Kingston’s historic downtown, join The Haunted Walk of Kingston for an atmospheric lantern-lit stroll through alleys and courtyards brimming with local lore. Guides bring centuries of true tales and legends to life—an unforgettable way to close your first day in Canada’s oldest city.
Day 2:
Morning
Step back into Confederation-era Kingston at Bellevue House National Historic Site, the former home of Sir John A. Macdonald. Operated by Parks Canada, the site invites reflection on nation-building, politics, and legacy through interpretive storytelling, costumed guides, and heritage gardens overlooking the lake.
Afternoon
Tour the legendary Kingston Penitentiary, one of Canada’s most compelling heritage experiences. Knowledgeable guides—some retired corrections staff—share stories of daily life and reform inside this formidable limestone structure. Various tour formats (45-minute express tour; 90-minute standard tour; two-hour extended tour) make it ideal for both groups and FIT travellers. Open from spring through fall, with limited specialty programs in shoulder seasons.
Lunch
For lunch, savour fresh Mediterranean-inspired dishes at Olivea, enjoy a blend of seafood and Mexican flavours at Dianne’s, or experience heritage-style comfort dishes at Black Dog Tavern. Each location offers pre-booked group options and fits perfectly into the historical and cultural rhythm of a Kingston visit, complementing the morning’s heritage experiences with vibrant local flavours.
Evening
Board a Kingston 1000 Islands Cruise (May–October) to see Kingston’s harbour and fortifications from the water or opt for a private Kingston Trolley charter for a narrated loop through the city’s heritage districts. Both experiences offer flexible itineraries suited to group schedules and sunset departures.
Day 3:
Morning
Begin at the Military Communications and Electronics Museum, home to one of Canada’s most unique military collections. Exhibits showcase everything from early field radios to modern satellites, pairing technology with human stories of service and innovation. The museum welcomes group visits year-round with guided tours available by request.
Late morning / afternoon
Continue to the Museum of Health Care, housed in the Ann Baillie Building National Historic Site on the Kingston Health Sciences campus. Here, Canada’s medical milestones come to life through rare artifacts and interactive displays. Group programming and educational tours are available throughout the year.
Follow with a light lunch nearby at the lakeside Juniper Cafe, and a self-guided wander through Queen’s University’s heritage district, where limestone buildings and commemorative plaques trace Kingston’s role in shaping Canadian education and innovation.
Evening
Conclude your visit aboard the Kingston Trolley Tour (operating year-round, by request). The City Tour circuit ties together Kingston’s museums, attractions, and waterfront landmarks—perfect for recapping three days of discovery while planning your next return.
Trade and group notes
Ideal seasons: Year-round; Kingston Penitentiary, Fort Henry, Bellevue House, S.S. Keewatin tours, and Kingston 1000 Islands Cruises operate seasonally (May–October).
Group readiness:
Fort Henry and Kingston Pen Tours offer dedicated group booking lines and guided tours.
Great Lakes Museum and S.S. Keewatin accommodate motorcoach parking and private tours.
Museums welcome custom itineraries and combined passes, such as KPASS.
FIT-friendly experiences: The Haunted Walk of Kingston, Kingston Trolley Tours, and select museums are open year-round.
Accessibility: Most attractions feature accessible entrances and washrooms; advance notice is recommended for group mobility requirements.
Hotels: Delta Hotels by Marriott Kingston Waterfront, Residence Inn Kingston Water’s Edge, Hampton by Hilton Kingston, and Holiday Inn Kingston-Waterfront provide a range of options for groups and FIT travellers, offering downtown or waterfront locations with easy access to all itinerary stops.
Suggested length: 2–3 days; all locations within 15 minutes of downtown.
