10 Best Boston Multiday Tours in October 2026

Essential East Coast, Niagara And Chicago - October 2026

8% OFF TODAY

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Essential East Coast, Niagara and Chicago - October 2026

No booking fees

Best price guaranteed

From the bright lights of New York to the architectural wonders of Chicago, the 'Essential East Coast, Niagara and Chicago' tour is a 14-day city sightseeing trip designed for seniors. This guided journey covers Detroit, Toronto, and other key destinations, with all logistics managed for your ease. The highlight is its comprehensive route, encompassing both historic and modern marvels in an itinerary that balances excitement with comfort.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

New York, Chicago, Niagara Falls

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

8% OFF TODAY

Duration14 days

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18% OFF TODAY

Fall Colours of New England - October 2026

No booking fees

Best price guaranteed

If the idea of New England brings images of picture perfect villages, sleepy fishing towns, vast swathes of golden beaches and presidential summer homes into your mind’s eye, this trip will not disappoint. Starting in historic Boston you’ll visit lovely Cape Cod, stunning Stowe and sea swept Maine, all adorned in vibrant fall foliage.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Lodge, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Boston, Plymouth, Cape Cod, Prov

Boston, Plymouth, Cape Cod, Providence, Killington, Vermont, North Conway

18% OFF TODAY

Duration10 days

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Indulgence in Eastern Canada - October 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 - October 2026

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From Washington to Las Vegas - October 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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Treasures of Cape Cod & the Islands, a Women-Only Tour - October 2026

No booking fees

Best price guaranteed

Embrace history and glamour on this 8-Day women-only tour as you travel with a small group from Massachusetts to Rhode Island. Follow the red-brick Freedom Trail in Boston to see where the U.S. took shape. On the shores of Cape Cod Bay, see Plymouth, a coastal town famous for its rich history as the landing site of the Pilgrims in 1620; visit the living history museum at Plimoth Patuxet. At Martha's Vineyard, pass the former home of Jacqueline Kennedy Onassis and to Oak Bluffs, an idyllic town with gingerbread-like cottages. Indulge in a Sea-to-Table feast filled with fish caught from local fishermen, fresh produce from nearby farms and delicacies picked by foragers. In the seaside city of Newport, board an 80-foot schooner to cruise the coastline, taking in views of historical buildings and the homes of the rich and famous — and learn about the area’s past as a pirates’ haven.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Boston, Sandwich, Martha's Viney

Boston, Sandwich, Martha's Vineyard, Newport, RI

Duration8 days

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East Coast And Dreamed Canada - October 2026

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East Coast and Dreamed Canada - October 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 - October 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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East Coast Essential End Toronto - October 2026

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East Coast Essential End Toronto - October 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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Touring The East Coast From Washington - October 2026

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Touring the East Coast from Washington - October 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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The Grand East - October 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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From Washington To San Francisco - October 2026

8% OFF TODAY

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From Washington to San Francisco - October 2026

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

8% OFF TODAY

Duration18 days

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Essential East Coast And Unmissable West - October 2026

8% OFF TODAY

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Essential East Coast and Unmissable West - October 2026

No booking fees

Best price guaranteed

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

8% OFF TODAY

Duration23 days

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

8% OFF TODAY

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

8% OFF TODAY

Duration19 days

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All Boston Tours in October 2026

19 Trips in Boston during October 2026 with 59 Reviews

Get a customized trip to Boston in October 2026

19 Trips in Boston during October 2026 with 59 Reviews

Essential East Coast, Niagara and Chicago - October 2026

Fall Colours of New England - October 2026

Islands of New England - October 2026

Indulgence in Eastern Canada - October 2026

From Washington to Las Vegas - October 2026

Treasures of Cape Cod & the Islands, a Women-Only Tour - October 2026

East Coast and Dreamed Canada - October 2026

Discover Eastern US and Canada - October 2026

East Coast Essential End Toronto - October 2026

Touring the East Coast from Washington - October 2026

The Grand East - October 2026

From Washington to San Francisco - October 2026

Essential East Coast and Unmissable West - October 2026

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

19 Trips in Boston during October 2026 with 59 Reviews

Get a customized trip to Boston in October 2026

19 Trips in Boston during October 2026 with 59 Reviews