10 Best Boston Multiday Tours in September 2026

Indulgence in Eastern Canada - September 2026

4.5

(2 reviews )

No booking fees

Best price guaranteed

It was great. I enjoyed all of the places. Would like more time to shop.

City sightseeingFood tours

Tour Type

Group Tour

Accommodation

Hotel, Luxury Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Toronto, Boston, Ottawa, Quebec

Toronto, Boston, Ottawa, Quebec City, Montreal

Duration8 days

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From Washington To Las Vegas - September 2026

8% OFF TODAY

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From Washington to Las Vegas - September 2026

No booking fees

Best price guaranteed

Set off on a grand adventure from the nation’s capital to the entertainment capital of the world with the "From Washington to Las Vegas" city sightseeing tour. Spanning 21 days, this group trip covers Boston, New York, and 10 other destinations throughout the USA and Canada—crafted for seniors who value comfort and cultural immersion. With hotels, transport, and meals seamlessly included, you can relax and enjoy the journey’s diverse highlights. The tour’s unique selling point is its extensive, cross-country route, allowing you to experience a remarkable variety of cities and landscapes in one cohesive package.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., Las Vegas, Toro

Washington D.C., Las Vegas, Toronto, Niagara Falls, Detroit, Chicago, Los Angeles, Flagstaff, New York, Boston, Montreal, Quebec City, Ottawa

8% OFF TODAY

Duration21 days

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Eastern Round Ends Chicago - September 2026

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Eastern Round ends Chicago - September 2026

No booking fees

Best price guaranteed

Journey through the heart of America’s eastern region with the 16-day 'Eastern Round ends Chicago' tour. Perfect for seniors who seek a blend of history and culture at an easy pace, this trip weaves together Toronto, Chicago, Detroit, and more. The itinerary is packed with visits to cultural, historic, and religious landmarks, all with group guidance, comfortable accommodation, and all meals included. The unique draw of this package is its comprehensive sweep of the eastern USA, allowing travelers to immerse themselves in a variety of cityscapes and traditions with complete peace of mind.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., Chicago, Toront

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

8% OFF TODAY

Duration16 days

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New England's Fall Foliage, a Women-Only Tour - September 2026

No booking fees

Best price guaranteed

With a tapestry of vibrantly coloured leaves at every turn, New England in the autumn is a sight to behold. On this eight-day guided women-only tour, explore Boston, one of the oldest cities in the U.S., walking part of the red-brick Freedom Trail and seeing the hall that housed the country’s first-ever town meeting. Marvel at the bronzing leaves of Vermont’s trees as you travel to Stowe and visit the women-owned and -managed Bread and Butter Farm. In Montpelier, delight in a visit to a maple syrup farm where you can taste the sweet golden liquid tapped straight from the trees. Ascend a gondola at Loon Mountain Resort into New Hampshire’s White Mountains and join a MAKE TRAVEL MATTER® Experience for an insightful talk by a woman who is an expert on the North Woods' wildlife and ecology. With your small group of like-minded travellers, celebrate your trip with a decadent lobster dinner.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel, Lodge, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Boston, Saratoga Springs, Stowe

Boston, Saratoga Springs, Stowe, North Conway, Portland, ME

Duration7 days

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Whashington, Ny With Capites Canadienses End Ny - September 2026

8% OFF TODAY

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Whashington, NY with Capites Canadienses end NY - September 2026

No booking fees

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Venture through North America’s historic capitals on the "Whashington, NY with Capites Canadienses end NY" sightseeing tour. Spanning 14 days, this journey is tailored for seniors who appreciate a relaxed pace and comprehensive exploration. Starting in Washington D.C. and ending in New York, the itinerary includes stops in Quebec City, Montreal, and several US destinations. With comfortable hotels, seamless transport, and meals included, you’ll travel in ease and style. The tour’s unique draw is its cross-border experience, offering a blend of American and Canadian culture and history in one thoughtfully designed package.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Washington D.C., Toron

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

8% OFF TODAY

Duration14 days

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East Coast And Dreamed Canada - September 2026

8% OFF TODAY

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East Coast and Dreamed Canada - September 2026

(1 review )

No booking fees

Best price guaranteed

Everything was well arranged

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Niagara Falls, Boston

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

8% OFF TODAY

Duration12 days

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Discover Eastern US and Canada - September 2026

Trip customizable

Best price guaranteed

This tour takes you through the scenic landscapes of New England and the iconic cities of Eastern America and Canada. Begin in New York City, the bustling metropolis known as “the city that never sleeps,” before heading north to Boston — one of America’s oldest cities and a birthplace of its fight for independence. Walk the historic Freedom Trail and experience the charm of Beacon Hill’s cobblestone streets. Travel through the picturesque New England states of New Hampshire and Vermont before crossing the border into Canada. Arrive in Quebec City, a UNESCO World Heritage Site, where French heritage and Old World charm come alive within its fortified walls. Continue to Montreal, a lively and culturally rich city filled with historic architecture and vibrant neighborhoods. From there, journey to Ottawa, known for its stately parliament buildings and green open spaces, before making your way to Toronto — Canada’s largest city and a showcase of modern urban life. Witness the awe-inspiring power of Niagara Falls, one of North America's greatest natural wonders. Return to the United States and travel through upstate New York to Gettysburg, the site of the most significant battle of the American Civil War. Explore the traditions of the Amish community in Pennsylvania Dutch Country, then continue to Washington, D.C., where you’ll discover the iconic monuments and institutions that define the nation’s capital. Conclude your journey with a visit to Philadelphia, where the foundations of American democracy were laid, before returning to New York City.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

New York, Washington D.C., Montr

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

Duration11 days

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Eastern Discovery - September 2026

Trip customizable

Best price guaranteed

This epic journey takes you through the best of big city excitement and wild natural beauty. You’ll go from sophisticated Manhattan and cultural Boston to cosmopolitan Montreal and inspiring national monuments in D.C. Visit vibrant cities like New York, Toronto, and Montreal, plus historical places like the UNESCO world heritage sites of Old and New Québec City, and the world-famous Niagara Falls. You'll make memories for a lifetime and gain a new appreciation of the east coast

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

New York, Boston, Quebec City, M

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

Duration11 days

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East Coast Essential End Toronto - September 2026

8% OFF TODAY

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East Coast Essential End Toronto - September 2026

No booking fees

Best price guaranteed

The 'East Coast Essential End Toronto' tour invites you on a 10-day city sightseeing journey from New York to Toronto, stopping in Montreal, Quebec City, Ottawa, and more. Perfect for seniors, the trip is paced for comfort, with included accommodations, transport, and meals. Its unique selling point is the curated route through some of eastern North America’s most fascinating cities, offering both cultural depth and ease of travel.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Toronto, Boston, Montr

New York, Toronto, Boston, Montreal, Quebec City, Ottawa

8% OFF TODAY

Duration11 days

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Ultimate Canada - September 2026

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

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Touring The East Coast From Washington - September 2026

8% OFF TODAY

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Touring the East Coast from Washington - September 2026

No booking fees

Best price guaranteed

For those who crave a taste of both American and Canadian capitals, the 'Touring the East Coast from Washington' trip provides a 9-day journey from Washington D.C. to Quebec City. This easy-paced sightseeing tour is especially suitable for senior travelers, with accessible activities and thoughtfully arranged accommodations, meals, and transport. Along the way, you’ll explore Washington D.C., New York, and Quebec City, enjoying guided group experiences. The real charm of this tour lies in its seamless exploration of two nations’ most storied cities, making it a memorable and comfortable adventure.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Washington D.C., Quebec City, Ne

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

8% OFF TODAY

Duration9 days

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Patriot Trails - September 2026

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

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The Grand East - September 2026

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

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Autumn Colours - September 2026

4.9

(8 reviews )

No booking fees

Best price guaranteed

There is a free bus from the airport to the hotel the bb bus in bnostion.

National parksBeach

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Boston, Burlington, North Conway

Boston, Burlington, North Conway, Bar Harbor, Rockport, ME

Duration9 days

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All Boston Tours in September 2026

Page 2 of 38 Trips in Boston during September 2026 with 199 Reviews

Get a customized trip to Boston in September 2026

Page 2 of 38 Trips in Boston during September 2026 with 199 Reviews

Indulgence in Eastern Canada - September 2026

From Washington to Las Vegas - September 2026

Eastern Round ends Chicago - September 2026

New England's Fall Foliage, a Women-Only Tour - September 2026

Whashington, NY with Capites Canadienses end NY - September 2026

East Coast and Dreamed Canada - September 2026

Discover Eastern US and Canada - September 2026

Eastern Discovery - September 2026

East Coast Essential End Toronto - September 2026

Ultimate Canada - September 2026

Touring the East Coast from Washington - September 2026

Patriot Trails - September 2026

The Grand East - September 2026

Autumn Colours - September 2026

Europe

Asia

South America

Africa

North America

Oceania

Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

All Boston Tours in September 2026

Page 2 of 38 Trips in Boston during September 2026 with 199 Reviews

Get a customized trip to Boston in September 2026

Page 2 of 38 Trips in Boston during September 2026 with 199 Reviews