10 Best Boston Multiday Tours in September 2026

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Colors of New England - September 2026

4.8

(41 reviews )

No booking fees

Best price guaranteed

Couldn't have been better!

Art and architecture

Tour Type

Group Tour

Accommodation

Resort, Lodge, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Boston, Portland, OR, Stowe, North Conway, Portland, ME

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Duration8 days

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East Coast USA and Canada - September 2026

4.5

(13 reviews )

No booking fees

Best price guaranteed

North East USA y Canada tour was very well planned, we visited interesting places. Acommodations, food, experiences were very good. Tour director was excellent, his knowledge, organization, attention to details, caring, emphaty made this experience exceptional..thanks!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

New York, Quebec City, Montreal

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

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Duration14 days

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Eastern Round Ends Chicago - September 2026

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Eastern Round ends Chicago - September 2026

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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

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Duration16 days

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

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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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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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Touring The East Coast From Washington - September 2026

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Touring the East Coast from Washington - September 2026

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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

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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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Essential East Coast And Unmissable West - September 2026

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Essential East Coast and Unmissable West - September 2026

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Curious about the ultimate North American odyssey? The 'Essential East Coast and Unmissable West' tour delivers 23 days of city sightseeing from the bustling avenues of New York to the scenic charms of San Francisco. Crafted for seniors, this journey promises a relaxing pace through a dozen destinations, including Detroit, Chicago, and Los Angeles, as well as key cities in Canada. With comfortable hotels, group transport, and meals included, every detail is managed so you can focus on enjoying each locale. The standout feature is the tour’s extensive itinerary, offering a rare opportunity to experience both coasts and everything in between, all in one seamless trip package.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, San Francisco, Niagara

New York, San Francisco, Niagara Falls, Detroit, Chicago, Los Angeles, Las Vegas, Flagstaff, Bakersfield, Fresno, CA, Boston, Montreal, Quebec City, Ottawa, Toronto

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Duration23 days

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Essential East Coast And Western Classics, Ending In Las Vegas - September 2026

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Essential East Coast and Western Classics, Ending in Las Vegas - September 2026

(2 reviews )

No booking fees

Best price guaranteed

We enjoyed very much

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Las Vegas, Niagara Fal

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

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Duration19 days

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Colours of New England - September 2026

Trip customizable

Best price guaranteed

Embarking on a New England tour from Boston is a delightful journey through history, natural beauty, and iconic landmarks. This itinerary includes Cape Cod, Acadia National Park, the White Mountains, Vermont's White Mountains, Plymouth Rock, and Boston's historic Freedom Trail. This New England tour offers a perfect blend of history, natural beauty, and seasonal delights. Immerse yourself in the charm and allure of this picturesque region during the fall foliage season on a once-in-a-lifetime adventure

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Lodge, Resort

Age Range

13-99 yrs

Operated in

english

Destinations

Massachusetts, Boston, Portland

Massachusetts, Boston, Portland, ME, Bar Harbor, Bretton Woods, NH, White Mountains National Forest, Newport, RI, Cape Cod

Duration10 days

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Touring The East Coast End Toronto - September 2026

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Touring the East Coast end Toronto - September 2026

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

8% OFF TODAY

Duration13 days

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Essential East Coast And Western Classics - September 2026

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Super Sales

Essential East Coast and Western Classics - September 2026

No booking fees

Best price guaranteed

Explore the cultural treasures of North America on the 16-day 'Essential East Coast and Western Classics' tour, starting in New York and concluding in San Francisco. Designed with seniors in mind, this guided journey takes you through Montreal, Los Angeles, Bakersfield, and other vibrant cities. Enjoy leisurely sightseeing of historic and religious landmarks, all while staying in comfortable hotels and enjoying inclusive meals and transportation. What makes this tour stand out is its seamless blend of cultural heritage and modern cityscapes, ideal for those who appreciate both history and the comforts of well-organized group travel.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, San Francisco, Los Ang

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

8% OFF TODAY

Duration16 days

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All Boston Tours in September 2026

14 Trips in Boston during September 2026 with 64 Reviews

Get a customized trip to Boston in September 2026

Colors of New England - September 2026

East Coast USA and Canada - September 2026

Eastern Round ends Chicago - September 2026

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

Eastern Discovery - September 2026

Touring the East Coast from Washington - September 2026

Patriot Trails - September 2026

The Grand East - September 2026

Autumn Colours - September 2026

Essential East Coast and Unmissable West - September 2026

Essential East Coast and Western Classics, Ending in Las Vegas - September 2026

Colours of New England - September 2026

Touring the East Coast end Toronto - September 2026

Essential East Coast and Western Classics - 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

14 Trips in Boston during September 2026 with 64 Reviews

Get a customized trip to Boston in September 2026