10 Best Toronto Multiday Tours in September 2025

Unmissable Canada, Niagara and Chicago - September 2025

No booking fees

Best price guaranteed

Journey from French-speaking Montreal to the towering skyline of Chicago on the 11-day 'Unmissable Canada, Niagara and Chicago' sightseeing trip. Tailored for seniors, the itinerary features Montreal, Toronto, Quebec City, Niagara Falls, and more, offering a rich selection of North American highlights. Group guidance, comfortable hotels, and all meals and transport are included for an effortless experience. This tour’s unique benefit is its blend of Canadian culture and American city life, promising a vivid and accessible adventure.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Chicago, Montreal, Quebec City

Chicago, Montreal, Quebec City, Ottawa, Toronto, Niagara Falls, Detroit

Duration11 days

From

USD 2,236

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Super Sales

Ultimate Canada - September 2025

4.4

(9 reviews )

No booking fees

Best price guaranteed

Fantastic trip lead by an amazing trio manger. Well worth the cost. Admittedly the west coast was a lot better than that of the east mainly due to the scenery which was present. Special stays in Whistler as a pod hotel and Banff as a chalet with friend made the trip that much more special. The feee time add ones were also really reflective of the areas we visited and appropriately priced. Would highly recommend.

National parksWaterfalls

Tour Type

Group Tour

Accommodation

Hotel, Lodge, Resort

Age Range

18-35 yrs

Operated in

english

Destinations

New York, Vancouver, Ottawa, Whi

New York, Vancouver, Ottawa, Whistler, Sun Peaks, Jasper, Banff, Vernon, Quebec City, Montreal, Niagara Falls, Toronto, Boston

Duration19 days

From

USD 4,565

USD 4,428

Saving

USD 137

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Toronto, Niagara and Chicago - September 2025

No booking fees

Best price guaranteed

Experience the vibrant energy of North America’s great cities with the 'Toronto, Niagara and Chicago' 7-day city sightseeing tour. Starting in Toronto and ending in Chicago, this trip is designed for seniors looking for a comfortable and comprehensive journey through Detroit, Niagara Falls, and other exciting locales. Hotels, transport, and meals are all included, making it easy to focus on the sights. The tour’s unique feature is its well-paced route, connecting urban and natural highlights in a single, seamless adventure.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Toronto, Chicago, Niagara Falls

Toronto, Chicago, Niagara Falls, Detroit

Duration7 days

From

USD 1,275

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From Montreal to Washington - September 2025

No booking fees

Best price guaranteed

Trace a route through North America’s most captivating cities with the 12-day 'From Montreal to Washington' city sightseeing tour. Ideal for seniors seeking a relaxed yet comprehensive experience, this guided journey covers Montreal, Toronto, Washington D.C., and additional classic destinations. All hotels, meals, and transport are provided, so you can immerse yourself in each city’s unique character. The tour’s special appeal lies in its cross-border itinerary, offering a window into both Canadian and American cultures in one well-organized package.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., Montreal, Quebe

Washington D.C., Montreal, Quebec City, Ottawa, Toronto, Niagara Falls, New York

Duration12 days

From

USD 2,438

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Patriot Trails - September 2025

Trip customizable

Best price guaranteed

Embark on an unforgettable Eastern USA and Canada tour starting from the historic city of Boston and winding your way through fascinating destinations, including Quebec City, Montreal, Ottawa, Toronto, Niagara Falls, Gettysburg, Washington D.C., and concluding in the vibrant metropolis of New York City. This journey will take you through a blend of cultures, history, natural wonders, and iconic landmarks, providing a diverse and enriching travel experience

Adventure

Tour Type

Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

New York, Massachusetts, Boston

New York, Massachusetts, Boston, Quebec City, Montreal, Toronto, Niagara, Amish Country, Washington D.C.

Duration9 days

From

USD 1,951

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Canada, Niagara and New York - September 2025

No booking fees

Best price guaranteed

Pack your bags for a 10-day adventure from Montreal to New York with the 'Canada, Niagara and New York' sightseeing tour. This group trip is tailored for seniors, providing a relaxed yet engaging pace through Ottawa, Toronto, and beyond. Enjoy guided experiences, comfortable hotels, and included meals and transport. The unique aspect of this package is its combination of Canadian hospitality and American energy, delivering an unforgettable cross-border journey.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Montreal, Quebec City

New York, Montreal, Quebec City, Ottawa, Toronto, Niagara Falls

Duration10 days

From

USD 2,032

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Unmissable Canada and Western Classics - September 2025

No booking fees

Best price guaranteed

Imagine tracing a route from Montreal to the Pacific, discovering iconic cities along the way—this is the promise of the 'Unmissable Canada and Western Classics' sightseeing tour. Over 13 days, this easy-paced trip is thoughtfully designed for mature travelers seeking both comfort and cultural richness. You'll journey from Montreal through Ottawa and onward to dynamic San Francisco, with memorable stops in both Canadian and American cities. Group guidance, quality hotels, comfortable transport, and included meals ensure a hassle-free experience. The tour’s unique appeal lies in its curated mix of urban highlights and scenic transitions across borders, offering a truly comprehensive North American adventure.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

San Francisco, Montreal, Fresno

San Francisco, Montreal, Fresno, CA, Quebec City, Ottawa, Toronto, Los Angeles, Bakersfield

Duration13 days

From

USD 3,233

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The Grand East - September 2025

Trip customizable

Best price guaranteed

Visit cosmopolitan cities and state-of-the-art places like the Kennedy Space Center which exhibits modern space-age technology. Gaze upon the many monuments and museums the American capital is famous for in Washington D.C. Stay in historic Quebec City and cosmopolitan Montreal and stop in Canada’s elegant capital Ottawa including Toronto, the largest city in Canada. Visit the musical cities of Nashville and Memphis before a stop in the jazz city of New Orleans. Travel to the Gulf Coast to Florida, stopping in Orlando, and ending in sunny Miami

AdventureCity sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

New York, Roanoke, Gatlinburg, N

New York, Roanoke, Gatlinburg, Nashville, Memphis, New Orleans, Pensacola, Orlando, Miami, Boston, Quebec City, Montreal, Toronto, Niagara, Amish Country, Mount Washington, Washington D.C.

Duration20 days

From

USD 4,058

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Toronto, Niagara and New York - September 2025

No booking fees

Best price guaranteed

From the cosmopolitan streets of Toronto to the iconic skyline of New York, the 'Toronto, Niagara and New York' trip offers a 6-day city sightseeing package that perfectly balances urban excitement and natural splendor. Seniors will find the itinerary thoughtfully paced, with included accommodations, meals, and transport ensuring a hassle-free experience. The real draw is the progression from Canada’s cultural heart to one of America’s greatest cities, all while taking in the majesty of Niagara Falls.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Toronto, Niagara Falls

Duration6 days

From

USD 1,094

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Unmissable Canada with East Coast - September 2025

No booking fees

Best price guaranteed

Uncover the charms of Canada and the USA on the 'Unmissable Canada with East Coast' sightseeing tour, spanning 13 days from Montreal to New York. Designed for senior travelers, this guided group trip covers highlights such as Toronto and Montreal, as well as the vibrancy of New York and other select cities. With all logistics taken care of, you’re free to enjoy the journey at your own pace. What sets this tour apart is its focus on both Canadian warmth and American dynamism, providing a balanced and memorable exploration.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Montreal, Washington D

New York, Montreal, Washington D.C., Quebec City, Ottawa, Toronto, Niagara Falls

Duration13 days

From

USD 2,642

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From Washington to San Francisco - September 2025

No booking fees

Best price guaranteed

From the historic streets of Washington D.C. to the iconic hills of San Francisco, the "From Washington to San Francisco" guided city sightseeing tour delivers an 18-day journey ideal for seniors. With stops in Montreal, San Francisco, and a range of vibrant American cities, this group adventure ensures comfortable accommodations, seamless transport, and included meals. The relaxed pace and varied itinerary make it an excellent choice for travelers seeking a thorough cross-country experience. Its USP is the rare opportunity to traverse the breadth of the USA while enjoying expert guidance and camaraderie.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., San Francisco

Washington D.C., San Francisco, Toronto, Los Angeles, Bakersfield, Fresno, CA, New York, Boston, Montreal, Quebec City, Ottawa

Duration18 days

From

USD 4,194

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Toronto and Western Classics - September 2025

No booking fees

Best price guaranteed

For a well-balanced introduction to the great urban centers of North America, the "Toronto and Western Classics" tour is a top pick. This 9-day city sightseeing group trip begins in Toronto and concludes in San Francisco, with additional time in Los Angeles. Designed for seniors, the tour includes comfortable hotels, meals, and transport, all at an easy pace. Its unique appeal lies in its blend of Canadian and American experiences—allowing you to sample the best of both countries with minimal effort.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Toronto, San Francisco, Los Ange

Toronto, San Francisco, Los Angeles, Bakersfield, Fresno, CA

Duration9 days

From

USD 2,402

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Touring the East Coast end Toronto - September 2025

No booking fees

Best price guaranteed

Picture yourself journeying from the heart of the USA to Canada’s cosmopolitan hub on the 'Touring the East Coast end Toronto' trip. Over 12 days, this guided city sightseeing tour leads you from Washington D.C. through Ottawa and Toronto, as well as several other key cities. Created for seniors, the pace is gentle and the logistics seamless: comfortable hotels, included meals, and group transport ensure a smooth experience. The unique advantage of this tour is its focus on both American and Canadian highlights—offering a cross-border adventure packed with cultural discovery and relaxation.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Toronto, Washington D.C., New Yo

Toronto, Washington D.C., New York, Boston, Montreal, Quebec City, Ottawa

Duration13 days

From

USD 2,641

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Toronto, Niagara with East Coast End Washington - September 2025

No booking fees

Best price guaranteed

From the thundering waters of Niagara Falls to the vibrant streets of Washington D.C., the 'Toronto, Niagara with East Coast End Washington' trip delivers 8 days of memorable city sightseeing. Ideal for senior travelers, this group tour starts in Toronto and ends in the U.S. capital, weaving through Canada’s and America’s top destinations. With all hotels, meals, and transport included, you can relax and savor each experience. The unique selling point is the curated route linking natural wonders with urban highlights for a well-balanced, easygoing adventure.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Toronto, Washington D.C., Niagar

Toronto, Washington D.C., Niagara Falls, New York

Duration8 days

From

USD 1,458

View Tour

All Toronto Tours in September 2025

Page 2 of 30 Trips in Toronto during September 2025 with 58 Reviews

Page 2 of 30 Trips in Toronto during September 2025 with 58 Reviews

Unmissable Canada, Niagara and Chicago - September 2025

Ultimate Canada - September 2025

Toronto, Niagara and Chicago - September 2025

From Montreal to Washington - September 2025

Patriot Trails - September 2025

Canada, Niagara and New York - September 2025

Unmissable Canada and Western Classics - September 2025

The Grand East - September 2025

Toronto, Niagara and New York - September 2025

Unmissable Canada with East Coast - September 2025

From Washington to San Francisco - September 2025

Toronto and Western Classics - September 2025

Touring the East Coast end Toronto - September 2025

Toronto, Niagara with East Coast End Washington - September 2025

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Special interests and hobbies

All Toronto Tours in September 2025

Page 2 of 30 Trips in Toronto during September 2025 with 58 Reviews

Page 2 of 30 Trips in Toronto during September 2025 with 58 Reviews