Montreal is a city that wears its history proudly. Unlike many North American cities, it’s layered with stories of French colonial roots, Jewish settlement, jazz evolution, and modern urban renewal. Exploring Montreal on a historical tour reveals the city’s complex identity, vibrant neighborhoods, and architectural marvels. We’re especially fond of tours that go beyond the surface — like the Making Their Mark: Montreal Jewish History Walking Tour which dives into the early 20th-century Jewish community in the Plateau. It’s a deeply personal and immersive experience that brings history to life through meaningful sites. For a different flavor, the Old Montreal: Private History Walking Tour with Tastings combines history with local cuisine, perfect for those who love a good story with their food.
Montreal offers a wide variety of guided walking tours, boat cruises, private explorations, and thematic walks, providing travelers with options tailored to interests and fitness levels. Whether you want a quick 1-hour cruise on the St. Lawrence or a comprehensive day trip exploring Quebec’s historic towns, this list has a lot to offer.
1. Making Their Mark: Montreal Jewish History Walking Tour
Gain insight into Canada’s colorful Jewish heritage on this engaging 2-hour walking tour in Montreal. Your guide takes you through the Plateau neighborhood, where waves of Jewish settlers arrived in the early 1900s. The tour covers synagogues, schools, hospitals, and cultural hubs that these community builders created from scratch. It’s a deeply human look at how this community helped shape Montreal’s identity. The tour begins and ends at different spots around the Plateau and Mile End, making it easy to link with other explorations. Many participants praise the knowledgeable guides, with one calling Emily “friendly and knowledgable,” and emphasizing the tour’s immersive storytelling. The moderate pace makes it family friendly, too.
What sets this tour apart is its focus on local stories and physical sites, like the Museum of Jewish Montreal, which the guide expertly references to animate the past. It’s perfect for history lovers interested in cultural diversity and community development. At just around $24 per person, the value is excellent.
Bottom Line: Rich in personal stories and meaningful sites, this tour offers a compelling introduction to Montreal’s Jewish community and its enduring legacy.
2. Rabbis, Writers and Radicals: Montreal Jewish History Walking Tour
This 2-hour tour explores Montreal’s Jewish literary, political, and social contributions, primarily in the Mile End district. For just $23.72, you get inside tips from a local guide who takes you through the streets where prominent Jewish authors, playwrights, and politicians once worked and socialized. You’ll visit key sites like libraries, social clubs, and synagogues, learning about the community’s resilience and influence. Tour participants highlight guide Serafina’s kindness and thorough knowledge, noting how she opens windows into the stories of early Jewish Montrealers. The tour begins and ends at different locations around the neighborhood, and public exhibitions are open nearby, adding context.
This experience is especially suited for those interested in literature, politics, and social change. The walking pace is moderate, making it accessible for most fitness levels. For a deeper dive into Montreal’s Jewish past, this tour provides a detailed, intimate view.
Bottom Line: A great choice for those wanting a culturally rich experience focused on influential figures and social history.
3. In the Shadow of the Mountain: Montreal Jewish History Walking Tour
Starting from the Museum of Jewish Montreal, this 2-hour interpretive walk explores Jewish neighborhoods with a focus on Mount Royal’s symbolism, called ‘Tur Malka’ by early Yiddish poets. Led by staff from the museum, the tour uses mobile tech to bring history to life, showing what life was like for Jewish residents trying to make Montreal their home. The tour covers diverse cultural conditions faced by the community, emphasizing their vibrancy despite adversity. Participants enjoy stories about community resilience, with Avery receiving praise for his extensive knowledge. The tour operates on several departures, making it flexible for travelers.
What makes this tour distinctive is its multimedia approach and emphasis on cultural symbolism tied to Mount Royal. It’s ideal for travelers interested in urban history, cultural identity, and community stories. At $23.72, it provides a rich experience for the price.
Bottom Line: An engaging, tech-enhanced walk that deepens understanding of Montreal’s Jewish neighborhoods and their connection to the city’s heart.
4. Montreal History Guided Sightseeing Cruise
Set sail for a scenic 1.5-hour cruise on the St. Lawrence River aboard the AML Cavalier Maxim. This is a relaxing way to see Montreal from a different perspective, admiring landmarks like the Jacques-Cartier Bridge, Boucherville Islands, and the Biosphere. The cruise combines stunning city views with stories about Montreal’s founding and legendary explorers, making it ideal for history buffs who enjoy a leisurely pace. The boat offers sunny terraces and glass-enclosed dining areas, perfect for chilling out while soaking up the scenery. Reviewers mention the tour as “well organized,” though some note that the narration can be continuous, which may be distracting for some.
This tour suits travelers who want a combination of sightseeing and storytelling on the water, especially those with limited time or seeking a relaxing experience. The slightly higher price reflects the boat amenities and scenic value.
Bottom Line: An enjoyable, scenic ride that offers both perspectives of Montreal’s skyline and its historic landmarks.
$34.09 per person
5. Day trip on Quebec Historic Road, Chemin du Roy (Montreal to Trois-Rivières)
For those with more time, this full-day tour hits the mark for exploring Quebec’s oldest highway, Chemin du Roy, built during France’s colonial era. Traveling by small group, you’ll visit towns like L’Assomption, Lavaltrie, and Trois-Rivières, discovering architectural treasures and historic sites. The highlight is Quebec City, with guided visits to Old Town and downtown, plus a pilgrimage at the Notre-Dame-du-Cap Basilica. The tour includes stops at historic houses and markets, with comments from local guides that make history tangible. Critics appreciate the well-paced itinerary and Mounir’s friendly, knowledgeable approach.
This trip is suited for history and architecture lovers seeking an in-depth look at Quebec’s past. The long 9-hour day is best for those comfortable with a bit of travel and walking.
Bottom Line: A comprehensive journey through Quebec’s historic towns, perfect for those wanting a full immersion in regional history and culture.
6. The 1-Hour Convertible Cadillac Old-Montreal History Tour SHARED
This is the classic Montreal experience in style—a 1-hour ride in a vintage convertible Cadillac. Starting at Bonsecours Market, you’ll cruise through Old Montreal’s cobblestone streets, passing Notre-Dame Basilica, Place Jacques-Cartier, and the Old Port. The small group in the open-top car makes it personal, with guides sharing stories from Montreal’s founding in 1642 to today’s lively city scene. Guests love the fun factor, with Olivier’s energetic narration and the chance to feel the breeze while admiring historic architecture. It’s a great choice for those who want a short, memorable introduction to Old Montreal.
The tour’s main limitation is its brevity, but it packs a lot into a single hour, making it perfect for tight schedules or as a fun side activity.
Bottom Line: A stylish, fun way to see Old Montreal’s highlights with a personal touch, ideal for first-timers or those short on time.
7. Black & Jazz History of Montreal with Ruby Roy Licensed Guide
This 2-hour private tour explores Montreal’s Black history and jazz scene, led by Ruby Roy, who has over 25 years of experience. Starting in Little Burgundy, you’ll see sites like the Atwater Market and the Lachine Canal, while hearing stories about jazz legends, prohibition-era nightlife, and the role of the railway in Black migration. The tour is designed for up to 15 people, creating a personal and detailed experience. Ruby’s deep knowledge shines as she shares her own research, making the history both educational and inspiring.
It’s a tour tailored for those interested in music history, civil rights, and multicultural stories. The private nature means you can customize the experience somewhat, and the size makes for an intimate setting. At $405 for the group, it’s an investment but well worth it for a unique perspective.
Bottom Line: A highly personalized journey into Montreal’s Black and jazz history, perfect for culturally curious travelers.
8. Private Montreal Car Tour with History and Hidden Gems
Explore Montreal at your own pace with this customizable 2 to 3-hour private car tour. It covers Old Montreal, Mount Royal, Plateau, and Little Italy, with stops where you can walk or drive. The guide shares stories about local culture, architecture, and secret spots like markets and cafes. Highlights include panoramic views from Mount Royal’s lookout and the colorful murals of the Plateau. This tour suits those who want a personalized experience without the hassle of navigating alone. Reviewers mention guides like Kian as “incredibly knowledgeable,” making this a flexible choice for families or first-time visitors.
Priced at $117.36 per person, the tour offers good value for private, customized exploration. It’s ideal for people who want a tailored experience that covers a broad swath of Montreal’s history and neighborhoods.
Bottom Line: A flexible, private way to discover Montreal’s history, culture, and hidden corners with a personal guide.
9. Old Montreal: Private History Walking Tour with Tastings
This 3-hour private tour combines history with culinary delights. Starting outside the Banque de Montreal, you’ll stroll through cobblestone streets, learning about Old Montreal’s past while sampling gourmet treats at each stop. Highlights include the architecture of Place d’Armes, historic buildings like Saint-Sulpice Seminary, and local shops. The tastings are carefully chosen to showcase Montreal’s gastronomic scene, making this perfect for food lovers interested in history. Participants praise guide David’s engaging storytelling and well-planned route, with some noting it skewed more toward sightseeing than food. The premium price reflects the personalized experience and gourmet tastings.
Ideal for those who want a culinary twist on history, this tour makes the past flavorful and fun.
Bottom Line: A delicious way to learn about Old Montreal’s history while enjoying local food and stories.
10. A Private Walk of Old Montreal: Historic & Cultural Sites
This private 2-hour walk offers a personal exploration of Old Montreal’s key sites, including Place d’Armes, Notre-Dame Basilica, and Old Saint-Sulpice Seminary. The route is flexible, allowing your guide to tailor the experience based on your interests. You’ll enjoy quiet moments in old courtyards, see lively public squares, and learn stories behind the architecture. The tour suits travelers who prefer an intimate, customized experience without the crowds.
Priced at $955 per group, it’s a premium option for those seeking exclusivity and a detailed narrative. Many appreciate the chance to ask questions and go at their own pace.
Bottom Line: An exclusive, flexible private tour ideal for history enthusiasts wanting a bespoke experience.
$955 per group up to 4
How to Choose the Right Montreal Historical Tour
Picking the best tour depends on your interests, schedule, and budget. If you’re passionate about Jewish history, the Making Their Mark or Rabbis, Writers and Radicals tours are excellent choices. Looking for a scenic experience? The Montreal Cruise offers a relaxing water-based perspective. For customized exploration, the Private Car Tour allows flexibility, while history and food lovers will enjoy the Old Montreal Tastings.
Consider your fitness level and whether you prefer walking, driving, or cruising. Booking early is wise during peak seasons, as these popular tours fill quickly, especially the private options.
Montreal’s history is woven into every street and building. From the Jewish neighborhoods and jazz clubs to the mighty St. Lawrence River, there’s a tour tailored to your curiosity. Whether you want a brief water cruise or a full-day journey into Quebec’s past, you’ll find plenty to enrich your visit. For a truly memorable experience, pick the tour that matches your interests and pace, and enjoy discovering what makes Montreal so unique.