Boston Tours in October 2026
Planning for a trip to Boston during October? We offer 10+ tour packages to Boston departing in October 2026 that have 50+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Boston on your October holiday.
See all Boston October 2026 Tours
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10 Best October 2026 Tours in Boston
Join one of these handpicked Boston October 2026 tour packages, tailored to the season.
40% Off Today
The Grand East trip is your gateway to the heart and soul of Eastern North America, blending iconic cityscapes with scenic countrysides on a 20-day adventure. Young adults and families will love this route, which kicks off in the bustling streets of New York before winding through the charming landscapes of New England, the historic Amish countryside, and on to the vibrant cities of Canada—Québec, Montréal, and Toronto.
Southward, immerse yourself in the musical energy of Nashville and New Orleans, then wrap up your journey with sun-soaked days in Florida. This tour stands out for its seamless combination of history, culture, and regional flair—a trip that lets you step back in time and savor modern delights, all in one grand package.
20 days
USD 6,796fromUSD 4,078
22% Off Today
Picture yourself wandering through the postcard-perfect landscapes of New England as autumn’s colors ignite every hillside. The "Fall Colours of New England" tour is a 10-day guided sightseeing trip beginning and ending in Boston, designed for experienced travelers, seniors, and families who appreciate vibrant scenery and charming towns. Visit historic Boston, stroll the sandy stretches of Cape Cod, and meander through the sleepy fishing villages and stately summer homes of Plymouth, Killington, and Maine. Comfortable group travel with included accommodation and meals ensures you can simply relax and enjoy the region’s famed fall foliage. The tour’s unique appeal? Its perfectly timed itinerary to catch New England’s most spectacular autumnal displays.
10 days
USD 2,775fromUSD 2,155
15% Off Today
Marvel at the autumnal splendor of New England on an eight-day guided tour designed with seniors and experienced travelers in mind. Starting in historic Boston, you’ll follow the red-brick Freedom Trail, uncovering the nation’s roots at landmarks like the site of the first town meeting. From there, journey through Vermont to Stowe, home to the real-life Von Trapp family, where you’ll enjoy the warmth and charm of a classic New England village.
Experience the sweet side of Vermont with a visit to a working maple syrup farm, sampling golden syrup straight from the source. In New Hampshire, revel in sweeping vistas from a gondola ride at Loon Mountain Resort, with views stretching all the way to Canada. Discover Maine’s maritime heritage at Portland’s oldest lighthouse and celebrate the region’s bounty with a sumptuous lobster dinner.
This tour package stands out for its seamless blend of striking fall foliage, cultural heritage, and regional flavors, making it an ideal trip for families and mature travelers seeking the quintessential New England experience in comfort and style.
8 days
USD 4,414fromUSD 3,767
13% Off Today
History buffs and culture seekers: the East Coast USA and Canada tour is your ticket to a 14-day exploration through the heritage-rich corridors of New York, Quebec City, Ottawa, Toronto, Montreal, and beyond. Stroll past the White House, experience the simplicity of Amish country, and marvel at the power of Niagara Falls. With all accommodations, transport, meals, and guided city sightseeing included, this easy-paced tour is tailored for travelers who want a deep dive into the stories and sites that define two nations. The highlight? Its seamless blend of American and Canadian icons, allowing you to connect with the diverse legacies of North America on a single, unforgettable trip.
14 days
USD 5,935fromUSD 5,181
3% Off Today
Explore stunning Eastern Canada on this 8-day guided tour. See Niagara Falls, one of the world’s most breathtaking natural wonders, as you cruise the iconic waters on a narrated boat tour. Later, explore the idyllic town of Niagara-on-the-Lake before indulging in an ice wine at Château des Charmes. Visit the most iconic sites of Ottawa, including its Parliament buildings and Rideau Canal, a UNESCO World Heritage Site — then feast on locally farmed and foraged foods for dinner at the renowned restaurant Play, Food & Wine. In Quebec City, stay at the Fairmont Le Château Frontenac, which overlooks the St. Lawrence River; a Local Expert will guide you through its corridors on a tour that take you into typically off-limits areas and unveils the mansion's unique history.
8 days
USD 5,447fromUSD 5,284
13% Off Today
This 8-Day guided tour blends history with glamour as you travel 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, a driver will take you past 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.
8 days
USD 5,188fromUSD 4,529
13% Off Today
See the top destinations in two countries on this 14-Day guided tour of Canada and the U.S. Stroll the urban-but-regal Queen's Park in downtown Toronto, then get up-close to the world’s most famous waterfall, Niagara Falls. Step inside the Notre-Dame Basilica-a masterpiece of Gothic Revival. Walk with a guide along part of the Freedom Trail in Boston, a 2.5-mile trail with 16 historically significant sites, including the house where the Boston Tea Party was planned in 1773. In Philadelphia, see the Liberty Bell, rung throughout history to announce some of the country’s most historical moments, such as the death of George Washington. In New York City, meet local vendors at a neighbourhood public market and taste local specialities.
14 days
USD 8,190fromUSD 7,150
40% Off Today
Craving a North American adventure that ventures beyond the ordinary? The Eastern Discovery tour sweeps you through the best of the US and Canada in 11 days, perfect for young adults and families seeking variety and excitement. Launch from the energetic streets of New York City, journey through Boston’s historic landmarks, and savor the charm of rural New England.
Cross into Canada to indulge in Quebec’s French flair, sample authentic maple syrup, and soak up stunning views along the Saint Lawrence River. Montréal and Toronto add cosmopolitan energy, with Lake Ontario’s beauty capping off your trip. The USP is its cross-border approach—blending iconic sights with regional delicacies and natural wonders for an all-encompassing tour package.
11 days
USD 3,771fromUSD 2,263
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
10 days
fromUSD 2,291
Experience the allure of New England’s autumn colors on this eight-day art and architecture tour, starting and ending in Boston. Ideal for those seeking a relaxed journey, the 'Colors of New England' group trip meanders through quintessential villages, sweeping mountains, and the rugged Maine coast.
Wander the leafy streets of Woodstock, Vermont, watch apples become cider at Cold Hollow Cider Mill, and learn about maple sugaring on a farm tour. Enjoy a scenic cruise on Lake Winnipesaukee and savor a classic New England lobster dinner. Ascend Mount Washington’s winding Auto Road and explore Portland’s coastal charm.
The standout feature? A thoughtfully paced itinerary that blends cultural traditions with natural beauty, ensuring you experience New England’s rich heritage and spectacular landscapes at their most vibrant.
8 days
fromUSD 3,949
See all Boston October 2026 Tours
Top Boston Tour Activities for October 2026
From cultural, religious and historic sites tours to adventure and others, here are some popular tour activities in Boston with departures in October 2026.
Boston October 2026 Tours for all Age Groups
Boston tours in October 2026 designed for all ages—families, young adventurers, seniors, and everyone in between.
Boston October 2026 Tour Types
Discover Boston October 2026 tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
Boston Travel Styles
Explore Boston with our diverse travel styles! Choose from luxurious tours that pamper you with comfort and elegance, or budget-friendly options that let you experience the beauty of Boston without breaking the bank. Whether you're indulging in fine dining or discovering hidden gems, there's a perfect adventure waiting for you.
