10 Best Boston Multiday Tours in October 2026

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Treasures of Cape Cod & the Islands - October 2026

4.9

(23 reviews )

No booking fees

Best price guaranteed

Everything about the trip was excellent. The hotels were very comfortable with superb food and service. The sights and venues were interesting with enough time a)lottery to see and enjoy them. The your director was great. She was creative in solving minor glitches. The driver was fantastic guiding the very comfortable but big bus through the narrow New England streets. The patrons were the most congenial group I have ever risen with. Top notch in every aspect.

ExplorerAdventure

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Boston, Plymouth, Cape Cod, Mart

Boston, Plymouth, Cape Cod, Marthas Vineyard, Newport, RI

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Duration8 days

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12% OFF TODAY

New England's Fall Foliage - October 2026

4.7

(6 reviews )

No booking fees

Best price guaranteed

The hotels are comfortable and interesting historically. The changing leaves made the ride on state and county roads an ever changing view. The itinerary includes city, village, and farm experiences that engage all the senses. Combined with a knowledgeable guide and pleasant co-travelers, this trip was one that I can heartily recommend.

Adventure

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

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Duration8 days

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Colors of New England - October 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

5% OFF TODAY

Duration8 days

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East Coast USA and Canada - October 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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18% OFF TODAY

Fall Colours of New England - October 2026

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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

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Duration10 days

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Islands of New England - October 2026

4.7

(54 reviews )

No booking fees

Best price guaranteed

I love the food. I have lived on the East Coast.

City sightseeingLocal culture

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

1-99 yrs

Operated in

english

Destinations

Cape Cod, Providence, Boston

Duration8 days

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Best of Eastern Canada and USA - October 2026

(5 reviews )

No booking fees

Best price guaranteed

Great tour itinerary with 2 x night accommodation at quality, well-located, hotels. Daily schedules included stops at highlights both en-route or at designated city stopovers, as well as sufficient “at leisure” time to explore independently. Our excellent Tour Director, provided insightful knowledge of destinations and recommendations throughout the tour. The coach transport was first-class as was our Driver. Availability of the on-board Wi-Fi and electronic device re-charging was particularly convenient. The Local Guides were engaging and professional.

ExplorerAdventure

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

New York, Toronto, Washington D.

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

15% OFF TODAY

Duration14 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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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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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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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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Autumn Colours - October 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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America's 250th - October 2026

No booking fees

Best price guaranteed

In honor of America’s 250th anniversary, trace the story of the nation’s rise on a journey through Boston, New York, Philadelphia, and Washington, D.C. Begin in Boston, where the American Revolution took root and venture to nearby Lexington and Concord, where the “shot heard ’round the world” was fired. Explore historic New York City on a panoramic tour and sit down for lunch in an 18th century tavern. In Philadelphia, see the Liberty Bell and reflect on the nation’s founding at the Museum of the American Revolution. Explore Washington, D.C., from the U.S. Capitol Building to the city’s iconic monuments and memorials, and visit George Washington’s estate, Mount Vernon. Be immersed in the history of a country found on the ideals of “Life, Liberty and the pursuit of Happiness” in 1776.

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Washington D.C., Boston, New Yor

Washington D.C., Boston, New York, Philadelphia

Duration9 days

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All Boston Tours in October 2026

13 Trips in Boston during October 2026 with 152 Reviews

Get a customized trip to Boston in October 2026

Treasures of Cape Cod & the Islands - October 2026

New England's Fall Foliage - October 2026

Colors of New England - October 2026

East Coast USA and Canada - October 2026

Fall Colours of New England - October 2026

Islands of New England - October 2026

Best of Eastern Canada and USA - October 2026

Indulgence in Eastern Canada - October 2026

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

Discover Eastern US and Canada - October 2026

The Grand East - October 2026

Autumn Colours - October 2026

America's 250th - October 2026

13 Trips in Boston during October 2026 with 152 Reviews

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

13 Trips in Boston during October 2026 with 152 Reviews

Get a customized trip to Boston in October 2026

13 Trips in Boston during October 2026 with 152 Reviews