Kingston, Ontario, is a city that packs a surprising punch when it comes to tours. With its lakeside setting, historic sites, and charming downtown, it’s a place where exploring on foot, by boat, or even from the air reveals stories that go beyond the usual tourist fare. We especially love the Kingston: Heart of the Thousand Islands Riverboat Cruise for its spectacular scenery and lively onboard entertainment, and the Ghosts and Mysteries Trolley Tour for a spooky twist on the city’s past. If you’re into historic architecture, the Trolley City Tour offers a nostalgic way to see Kingston’s 300-year history. Whatever your interests, Kingston’s variety of guided experiences makes it a fantastic destination for all types of travelers.
Quick Overview
Kingston’s tours cover a wide range of interests and formats, including scenic river cruises, evening dinners, ghost walks, trolley tours, and walking explorations. For boat lovers, there are options like the Thousand Islands Riverboat Cruise, offering stunning vistas and live music. History buffs can enjoy the Historic Downtown Walking Tour or the Trolley City Tour, which bring Kingston’s 300 years of stories to life. For those seeking a thrill, the Ghosts and Mysteries Trolley and Haunted Night Walking Tour reveal Kingston’s darker side. Ready? Let’s explore each one in detail.
1. Kingston: Heart of the Thousand Islands Riverboat Cruise
At number one, this 3-hour river cruise offers a quintessential Kingston experience. Departs from downtown Kingston, cruising into the stunning Thousand Islands, a region once called “The Millionaire’s Playground.” The paddlewheeler’s triple-deck design pays homage to classic Mississippi River steamboats, adding a nostalgic touch. This cruise isn’t just scenery; it’s lively, with onboard live musical entertainment that keeps the atmosphere upbeat. The scenery is the star here—rocky islands, lush forests, and historic lighthouses. Visitors often comment on the peaceful beauty of the region and the engaging commentary from the crew. The $47 ticket offers great value for a memorable afternoon. Perfect for those who want to relax and soak in a world-famous landscape, with a bit of musical fun thrown in.
Bottom line: A scenic, lively cruise that blends natural beauty with entertainment—ideal for first-time visitors or anyone wanting a taste of the Islands’ charm.
2. Kingston: Sunset Dinner Cruise
Number two on our list is a 3-hour Sunset Dinner Cruise offering a relaxed, romantic way to enjoy Kingston’s waterfront. For around $97, you’ll indulge in a three-course a-la-carte dinner while drifting past the Admiralty Islands as the sun dips low. The cruise provides spectacular sunset views—a photographer’s delight—and a chance to unwind with live music onboard. The cruise’s 4.4-star review score reflects its popularity, with many customers praising the quality of the meal and the beautiful setting. It’s especially suited for couples or special occasions, but anyone who enjoys a good meal with a view will find it worthwhile. Be prepared for a leisurely pace and a focus on ambiance.
Bottom line: A leisurely, scenic dinner cruise that’s perfect for romance or celebrating a special occasion, with excellent food and stunning sunset views.
3. Kingston: Ghosts and Mysteries Trolley Tour
Number three is a 1.5-hour guided trolley tour exploring Kingston’s darker past. With a star rating of 4.5 out of 5, this tour is a hit among those intrigued by the eerie stories of Kingston’s haunted sites. The trolley will take you through neighborhoods where Kingston’s ghostly legends come alive, including a visit to the grounds of Rockwood Asylum, one of the city’s most haunted buildings. Your guide shares tales of ghostly sightings, mysterious disappearances, and eerie happenings that have persisted for generations. The $39 price includes plenty of spooky stories and vivid history. It’s ideal for night owls and fans of the supernatural who like storytelling with a chill. Some might find the pace a little quick if they’re history buffs, but overall, it’s a fun, atmospheric experience.
Bottom line: Perfect for lovers of ghost stories and local legends, this trolley tour is a fun way to see Kingston’s haunted side after dark.
4. Kingston: Haunted Night Walking Tour
Next, the Haunted Night Walking Tour offers a 75-minute spooky stroll through Kingston’s downtown and Sydenham Ward. With a 4.5-star rating, this tour is a favorite for those who want to explore Kingston’s ghostly stories on foot. Your guide will tell tales of hangings, hidden burial grounds, and grave robbings, all set against the city’s atmospheric nightscape. The tour’s intimate size makes for a personal experience, and the stories are both intriguing and chilling. For only $24, it’s an affordable, captivating way to spend an evening. The walking pace is manageable, making it suitable for most fitness levels.
Bottom line: An engaging, spine-tingling walk through Kingston’s haunted streets, ideal for small groups or anyone interested in local ghost tales.
5. Kingston: Trolley City Tour
Number five is the Trolley City Tour, a delightful hour-long ride through Kingston’s historic downtown. This nostalgic trolley allows you to see key sights like Queen’s University, Kingston Penitentiary, and Fort Henry from a comfortable seat. With a 96-review rating and a price of $32, it offers a great way to get oriented, especially for first-timers. The guide shares stories covering more than 300 years of Kingston’s history, which helps put the city’s landmarks into context. The trolley runs every 30 minutes and allows you to hop off at any of the 10 stops if you want to explore further. It’s perfect for travelers short on time but eager to get a broad overview.
Bottom line: An easy, informative introduction to Kingston’s history, especially good for those who prefer a relaxed, scenic ride.
6. Kingston: Lunch Cruise of Thousand Islands
Number six combines a 3-hour cruise with a delicious onboard lunch, offering a relaxing way to see the Islands. For $73, you get to enjoy a meal while cruising through the scenic Thousand Islands region. The cruise features live entertainment and detailed descriptions of the scenery and local history, making it both entertaining and educational. The boat’s comfortable setting and generous meal make this a good value, especially if you want to combine sightseeing with tasty food. It’s well-suited for travelers who want a laid-back experience with plenty of photo opportunities. Be sure to book in advance, as this popular cruise fills quickly.
Bottom line: A relaxed, scenic cruise paired with a tasty lunch—ideal for those who want to combine food and scenery without rushing.
7. Kingston: Hop-On Hop-Off Trolley Tour
This 3-day pass is perfect for visitors who want to explore Kingston at their own pace. The Hop-On Hop-Off Trolley has 10 stops, including Fort Henry, Queen’s University, and the Penitentiary Museum. The 4.7-star review and flexible schedule make it an excellent choice for families or anyone who prefers a relaxed, self-paced exploration. Trolleys arrive every 30 minutes, giving you plenty of options to customize your day. The tour includes insightful commentary and easy access to major attractions. The $56 price offers solid value, especially with unlimited hopping over three days. It’s best for those who want to see all of Kingston without rushing or lugging around a guidebook.
Bottom line: The most flexible way to see Kingston’s highlights at your own pace, perfect for multi-day travelers.
8. Kingston: Brunch Cruise of Thousand Islands
Number eight is a brunch cruise aboard the Island Queen. Offering a delicious breakfast or brunch on St. Lawrence River, this experience combines scenic views with good food. Though specific reviews aren’t available, the concept is ideal for weekend mornings or special celebrations, providing a leisurely way to cruise and eat. The cruise showcases the remarkable scenery of the 1000 Islands while you enjoy freshly-prepared meals—perfect for a relaxed start to your day.
Bottom line: A laid-back, tasty way to see Kingston’s waterways while enjoying brunch, best suited for a leisurely morning outing.
9. Kingston: Waterfront Discovery Cruise
Number nine offers a 1-hour cruise along Kingston’s waterfront. It’s a quick, lively way to see Historic Sites like Fort Henry and Kingston Penitentiary from the water, with engaging narration. Rated at 4.1 out of 5, it’s a good option for a short, informative tour. The covered lower area makes it comfortable, and the top deck provides fresh air and views. At just $32, it’s an affordable introduction to Kingston’s waterway. It’s especially suitable for travelers short on time who still want a taste of Kingston’s history from a different perspective.
Bottom line: A concise, informative cruise that’s great for a quick overview of Kingston’s waterfront.
10. Kingston: Historic Downtown Walking Tour
Number ten is a 1-hour guided walk led by local expert Arthur Milnes. It explores highlights like Market Square and City Hall, with stories about Canadian Prime Ministers, Indigenous leaders, and even the Queen. With a 4.5-star rating, it offers small group intimacy and fascinating anecdotes, making history feel alive. For only $22, it’s an affordable way to engage deeply with Kingston’s past. The tour is ideal for history enthusiasts who like storytelling and a relaxed pace, with plenty of photo stops along the way.
Bottom line: A compact, engaging walk through Kingston’s historic core, perfect for history buffs and curious travelers alike.
11. Hidden Kingston City Walking Tours
Rated 5/5 from just 4 reviews, this quirky 1.5-hour tour explores Kingston’s offbeat side. Expect tales of duels, sea serpents, and costly mistakes. The guide’s fun storytelling style makes it a hit for those who like humor with their history. The tour’s accessible starting point and the chance to see historic buildings up close make it a favorite for small groups. The $28 price is a good deal for an hour and a half of discovery and giggles. It’s perfect for travelers wanting a humorous, less conventional look at Kingston.
Bottom line: A fun, unusual tour that uncovers Kingston’s lesser-known stories, ideal for lighthearted history lovers.
12. From Montreal: Kingston City Day Trip & 1000 Island Cruise
Number twelve offers a full-day guided trip, including hotel pickup in Montreal, a tour of Kingston’s landmarks, and a cruise in the Thousand Islands. Priced at $122, this option is great for travelers short on time but wanting a comprehensive experience. Highlights include Kingston City Hall, Royal Military College, and an opportunity to explore downtown’s shops. The cruise is a highlight, offering scenic views and commentary. The convenience of pickup and drop-off makes it especially appealing for visitors without their own transport.
Bottom line: An efficient, all-in-one day trip for those who want a deep dive into Kingston’s sights and scenery with minimal planning.
13. Kingston: Waterfront Shipwreck Cruise with Guide
This guided 1.5-hour cruise focuses on Kingston’s maritime wrecks. The $32 price makes it accessible, and the Great Lakes Museum guide shares stories of how these wrecks occurred. It’s ideal for maritime enthusiasts interested in shipwreck history and natural forces that shaped the harbor. The cruise explores Kingston’s shipwreck stories and the area’s maritime past in a relaxed setting. Though the review is modest, the focus on shipwreck stories adds a unique twist for history and nautical buffs.
Bottom line: An interesting, niche cruise that deepens your understanding of Kingston’s maritime history.
$32 per person
14. Kingston City Tour
Last but not least, the aerial Kingston City Tour offers a 30-minute flight over Kingston’s landmarks. For $236, this is a splurge, but it provides bird’s-eye views of Fort Henry, Kingston Penitentiary, and Garden Island shipwrecks. It’s perfect for those who want a quick, spectacular overview from above and see Kingston from a totally different perspective. The tour’s high price reflects its unique vantage point, making it ideal for aviation fans or special occasions.
Bottom line: A brief but stunning way to see Kingston’s key sites from the sky, suited for travelers who appreciate a panoramic view.
$236 per person
How to Choose the Right Tour
When deciding which tour to book, consider your interests, budget, and physical activity level. If scenery and a relaxed pace are your priority, the Riverboat Cruise or Lunch Cruise are excellent choices. For history buffs, the Historic Downtown Walking Tour or the Trolley City Tour offer in-depth stories and easy access. Ghost lovers should not miss the Ghosts and Mysteries Trolley or the Haunted Night Walking Tour—both deliver spine-tingling tales with different atmospheres. For a flexible visit, the Hop-On Hop-Off Trolley allows you to see as much as possible over multiple days, while the day trip from Montreal packs in a lot for travelers with limited time.
Booking early is recommended, especially for popular cruises and multi-day passes. Also, consider the season—summer offers the best weather for outdoor tours, but Kingston’s charm can be enjoyed year-round.
Final Thoughts
Whether you’re after scenic boat rides through the Thousand Islands, spooky ghost stories, or a quick glimpse from the sky, Kingston has a tour to match your interest. For a relaxed day on the water, the Heart of the Thousand Islands Riverboat Cruise is a standout, blending scenery with entertainment. History lovers will find plenty to fascinate, from walking tours to trolley rides exploring Kingston’s 300-year story. And if you’re feeling adventurous, the shipwreck cruise offers a unique maritime perspective.
Remember, early booking is wise for the most popular experiences. With such a diverse lineup, Kingston’s tours promise memorable ways to experience this charming lakeside city. Pick what suits your style, and you’ll leave with stories worth telling.