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    5. Freedom Trail and Little Italy Private Walking Tour
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    Freedom Trail and Little Italy Private Walking Tour

    See all 16 Freedom Trail sites and Little Italy with a private guide in 4.5 hours

    From$515

    Duration

    4 hour 30 min

    Ideal For

    Up to 15 people

    Highlights

    Explore all 16 stops of Boston’s Freedom Trail and detour through historic Little Italy on a private walking tour. Hear lively stories from a longtime resident and former city employee, with free time for lunch along the way.

    • Visit all 16 Freedom Trail sites including Old North Church and Paul Revere House
    • Start at Boston Common Visitor Center at 139 Tremont St
    • Walk a route led by a longtime resident and former city employee
    • Enjoy free time for lunch at an artisanal market or the oldest restaurant in America
    • Join a group of up to 15 on a private tour
    • Bring comfortable clothes and shoes

    What's Included

    • Tour guide services

    Things to know

    This is a walking-only tour with no vehicle. Maximum 15 people per tour. Tour starts at Boston Common Visitor Center.

    Cancellation policy

    Full refund if you cancel at least 14 days before your tour. 50% refund if you cancel at least 7 days before. No refunds within 7 days.

    Meeting location

    Tour starts at Boston Common Visitor Center (139 Tremont St., Boston)

    Experience provided by Boston Hidden Gems
    Experience provided by Boston Hidden Gems

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Reference #EX57JW

    Large Private Group

    $515.93

    0

    Why book through Greetwell?

    • Greetwell Approved

      This experience meets our quality and safety standards

    • Includes Concierge Support

      Our team is here to help with questions, timing, or special requests

    • Flexible Cancellation

      Plans change? Most experiences offer flexible cancellation

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    Review summary

    Jenny stands out as an exceptional guide in these reviews, earning consistent praise for her deep knowledge, engaging storytelling style, and warm personality. Travelers appreciate how she blends historical facts with modern context to keep tours interesting, and she's always happy to snap photos and answer questions. Alexandria also gets mentioned for excellent university tours covering MIT and Harvard. The operation runs smoothly with convenient door-to-door service that works well for visitors with limited mobility or tight schedules. This family-owned company clearly delivers personalized experiences. One family raved about booking a private Castles and Curses tour with guide Maria, who customized their itinerary and fielded endless questions about Massachusetts history and culture. The flexibility to accommodate individual interests shows up repeatedly, whether it's tailoring a tour for an elderly visitor interested in history or adjusting stops along the way. With perfect ratings across the board, this provider combines knowledgeable guides with thoughtful service that makes exploring Boston genuinely enjoyable.

    What people are saying

    Review 1 of 3
    5/5

    Great tour and outstanding customer service. This was the perfect fit for my Dad (80 yrs old) who had limited time in Boston and was on his own while I was at work. The guides were personable, knowledgeable and catered to my Dad's particular interests in history. Seamless operations with door-to-door service.

    Photo of Rachael Lammers

    Rachael Lammers

    January 11, 2026

    Review 1 of 1
    5/5

    Great tour and outstanding customer service. This was the perfect fit for my Dad (80 yrs old) who had limited time in Boston and was on his own while I was at work. The guides were personable, knowledgeable and catered to my Dad's particular interests in history. Seamless operations with door-to-door service.

    Photo of Rachael Lammers

    Rachael Lammers

    January 11, 2026

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