10 Best Boston Multiday Tours in October 2026

Treasures Of Cape Cod & The Islands - October 2026

13% OFF TODAY

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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

13% OFF TODAY

Duration8 days

From

USD 5,188

USD 4,529

Saving

USD 659

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New England's Fall Foliage - October 2026

15% OFF TODAY

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New England's Fall Foliage - October 2026

No booking fees

Best price guaranteed

Embrace the beauty of New England during this 8-Day guided tour. Behold Boston, one of the oldest cities in the U.S. and where much of the country was formed; here, you will traverse part of the red-brick Freedom Trail, where you will see the hall that housed the country’s first-ever town meeting and many more historic sites. Admire the bronzing leaves of Vermont’s lush trees as you travel to Stowe, where the real Von Trapp family of ‘The Sound of Music’ chose to live — and where you will stay. In Montpelier, visit a maple syrup farm where you can taste the sweet golden liquid tapped straight from the trees. Ride a gondola at Loon Mountain Resort into New Hampshire’s White Mountains and see as far as Canada. See Maine’s oldest lighthouse in Portland, then celebrate your trip with a decadent fresh lobster dinner.

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

15% OFF TODAY

Duration8 days

From

USD 4,414

USD 3,767

Saving

USD 647

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Fall Colours Of New England - October 2026

22% OFF TODAY

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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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40% OFF TODAY

The Grand East - October 2026

No booking fees

Best price guaranteed

An epic blend of the peace and calm of the New England countryside, the mojo of East Coast giants New York and Boston, the cultural extravaganza of the south from Nashville to New Orleans, and the energy of Florida… This is what you will find in the 20-day trip to the Grand East of the USA. Step back in time in the beautiful and culture-laden Amish countryside and let the hidden pockets of history unravel before your eyes in New England’s myriad attractions. Go beyond the US and dive into the cityscapes of Canada, with three days in Québec, Montréal, and Toronto. In the heart of the east, Nashville, Memphis, and New Orleans will sweep you off your feet with more culture and sophistication than you can handle. And, there is no better way to end a trip than three thrilling days in the sunshine state, of Florida.

Adventure

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-75 yrs

Operated in

english

Destinations

New York, Miami, Roanoke, Gatlin

New York, Miami, Roanoke, Gatlinburg, Nashville, Memphis, New Orleans, Pensacola, Orlando, Boston, Quebec City, Montreal, Toronto, Niagara Falls, Amish Country, Washington D.C.

40% OFF TODAY

Duration20 days

From

USD 7,104

USD 4,262

Saving

USD 2,842

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40% OFF TODAY

Eastern Discovery - October 2026

No booking fees

Best price guaranteed

If you are looking for a truly Eastern adventure in North America reaching beyond the borders of the US, the Eastern Discovery tour is just for you. You will cover a vast space in the eastern part of the US and Canada, taking a tour of must-see natural landscapes and incredible cities. The spectacular New York City will be the perfect launchpad for this all-in adventure, and you will dive deep into history in significant landmarks like Freedom Trail and King’s Chapel in Boston City. On your way to the border, rural New England is beckoning with lovely towns in New Hampshire and Vermont. In Quebec, lose yourself in an ocean of French Canadian delicacies, authentic maple syrup, and breathtaking views of the Saint Lawrence River. More Canadian flair will find you in Montréal, but what will struck you with awe is Toronto’s luminescent Lake Ontario.

Adventure

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-75 yrs

Operated in

english

Destinations

New York, Boston, Quebec City, M

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

40% OFF TODAY

Duration11 days

From

USD 3,821

USD 2,293

Saving

USD 1,528

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Best Of Eastern Canada And Usa - October 2026

13% OFF TODAY

Super Sales

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

13% OFF TODAY

Duration14 days

From

USD 8,190

USD 7,150

Saving

USD 1,040

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Super Sales

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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Eastern Discovery - October 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

From

USD 2,133

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Patriot Trails - October 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

From

USD 2,076

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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

View Tour

All Boston Tours in October 2026

11 Trips in Boston during October 2026 with 28 Reviews

Treasures of Cape Cod & the Islands - October 2026

New England's Fall Foliage - October 2026

Fall Colours of New England - October 2026

The Grand East - October 2026

Eastern Discovery - October 2026

Best of Eastern Canada and USA - October 2026

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

Eastern Discovery - October 2026

Patriot Trails - October 2026

The Grand East - October 2026

Colours of New England - October 2026

11 Trips in Boston during October 2026 with 28 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

11 Trips in Boston during October 2026 with 28 Reviews

11 Trips in Boston during October 2026 with 28 Reviews