10 Best Boston Multiday Tours in October 2026

Fall Colours Of New England - October 2026

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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

22% OFF TODAY

Duration10 days

From

USD 2,775

USD 2,155

Saving

USD 620

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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

From

USD 5,447

USD 5,284

Saving

USD 163

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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

From

USD 5,944

USD 5,766

Saving

USD 178

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Discover Eastern US and Canada - October 2026

Trip customizable

Best price guaranteed

This tour takes you through the scenic villages of New England and Iconic cities of Eastern America and Canada. Start your journey in New York - “the city that never Sleeps”. Drive to the historic city of Boston, one of oldest American municipality and home to some of the most important events of America’s Freedom struggle. Walk along the freedom trail and relive the stories of American Revolution. Next, cross the border and travel to the Historic City of Quebec, traversing through scenic New England with its picturesque villages and scenic mountains. Bask in the history of World UNESCO city of Quebec, one of the oldest cities in North America. Then drive to Montreal, the French infused Canadian City, known for its penchant for festivals and enjoying life. Later continue to the Canadian capital of Ottawa, the vibrant city of Parks and flowers, before reaching the truly cosmopolitan city of Toronto. Marvel at its amazing skyline, dominated by CN tower- one of the world’s tallest free-standing structures. Then, you get to wonder at the majestic Niagara Falls, before crossing the border back to US and make your way to Pennsylvania Dutch Country and discover the unique lifestyle of the Amish people. Travel through the Appalachian Mountains and visit the Gettysburg Civil War Memorial Battleground on your way to Washington, D.C. Explore the ins and outs of this magnificent city — the capital of the United States of America. Finally, end your journey with an incredible visit to Philadelphia, the legendary birthplace of America, where you will have the chance to visit the Independence Hall, the Liberty Bell or one of its many museums before you travel back to New York.

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

From

USD 2,204

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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

From

USD 4,224

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Colours of New England - October 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

From

USD 2,290

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All Boston Tours in October 2026

6 Trips in Boston during October 2026

6 Trips in Boston during October 2026

Fall Colours of New England - 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

Colours of New England - 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

6 Trips in Boston during October 2026

6 Trips in Boston during October 2026

Fall Colours of New England - 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

Colours of New England - October 2026