Boston Tours in October 2025
Planning for a trip to Boston during October? We offer 10+ tour packages to Boston departing in October 2025 that have 5+ 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 2025 Tours
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Select from 15+ tours
10 Best October 2025 Tours in Boston
Join one of these handpicked Boston October 2025 tour packages, tailored to the season.
3% Off Today
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.
14 days
USD 2,845fromUSD 2,760
40% Off Today
Autumn hues or summer charm, the Colors of New England tour delivers a 10-day journey through the heart of the Eastern United States. Launching from Boston, you’ll wander historic streets, visit charming coastal towns like Cape Neddick, and savor Portland’s culinary delights. Inland, the White Mountains beckon with breathtaking passes and tranquil forests.
Visit a traditional maple syrup farm to experience local culture, then unwind in Cape Cod’s coastal bliss before returning home. Perfect for young adults and families, this trip balances culture, history, and natural beauty. Its unique selling point is the immersion in New England’s traditions and landscapes—making every day a new discovery.
10 days
USD 4,502fromUSD 2,701
3% Off Today
Enjoy a classic journey along the US East Coast with the "Washington, NY and Boston" tour. Perfect for seniors, this 6-day sightseeing trip highlights the best of Washington D.C., New York, and Boston. With all accommodations, transport, and meals arranged, you can focus on soaking up each city’s unique personality and historic landmarks. The tour’s easy pace and expert guidance ensure a comfortable, worry-free experience. Its USP lies in the seamless access to three of America’s most storied cities within one concise, well-organized itinerary.
6 days
USD 1,197fromUSD 1,161
3% Off Today
Embark on a sweeping journey from Los Angeles to Chicago with the "USA and Canada Panorama with Chicago" guided city sightseeing tour. This 19-day adventure is crafted for seniors who enjoy discovering new places at a comfortable, easy-going pace. The itinerary covers highlights such as Fresno, New York, and nine other destinations, with group travel, hotel accommodations, and meals included. The tour’s USP is its broad scope—offering a rare look at both American and Canadian gems on one seamless itinerary.
19 days
USD 4,572fromUSD 4,435
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
3% Off Today
Set off from New York for a 12-day exploration of 'East Coast and Dreamed Canada,' where you’ll discover Boston, Quebec City, Niagara Falls, and more. This city sightseeing tour is designed for seniors, blending American dynamism with Canadian charm at an easy pace. With all accommodations, meals, and transport provided, you can focus on the sights. The key highlight is the combination of both countries’ best destinations, offering variety and relaxation in equal measure.
12 days
USD 2,438fromUSD 2,365
3% Off Today
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.
18 days
USD 4,194fromUSD 4,068
3% Off Today
Venture through North America’s historic capitals on the "Whashington, NY with Capites Canadienses end NY" sightseeing tour. Spanning 14 days, this journey is tailored for seniors who appreciate a relaxed pace and comprehensive exploration. Starting in Washington D.C. and ending in New York, the itinerary includes stops in Quebec City, Montreal, and several US destinations. With comfortable hotels, seamless transport, and meals included, you’ll travel in ease and style. The tour’s unique draw is its cross-border experience, offering a blend of American and Canadian culture and history in one thoughtfully designed package.
14 days
USD 2,845fromUSD 2,760
3% Off Today
Explore the cultural treasures of North America on the 16-day 'Essential East Coast and Western Classics' tour, starting in New York and concluding in San Francisco. Designed with seniors in mind, this guided journey takes you through Montreal, Los Angeles, Bakersfield, and other vibrant cities. Enjoy leisurely sightseeing of historic and religious landmarks, all while staying in comfortable hotels and enjoying inclusive meals and transportation. What makes this tour stand out is its seamless blend of cultural heritage and modern cityscapes, ideal for those who appreciate both history and the comforts of well-organized group travel.
16 days
USD 3,740fromUSD 3,628
3% Off Today
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.
11 days
USD 2,236fromUSD 2,169
See all Boston October 2025 Tours
Top Boston Tour Activities for October 2025
From city sightseeing tours to cultural, religious and historic sites and others, here are some popular tour activities in Boston with departures in October 2025.
Boston October 2025 Tours for all Age Groups
Boston tours in October 2025 designed for all ages—families, young adventurers, seniors, and everyone in between.
Boston October 2025 Tour Types
Discover Boston October 2025 tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
