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    1. Local experiences
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    5. /Private Freedom Trail & Little Italy Walking Tour in Boston
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    Private Freedom Trail & Little Italy Walking Tour in Boston

    Walk Boston's revolutionary landmarks and historic Little Italy with a local historian

    5.0 stars• 682 reviews

    Duration

    4 hrs 30 mins

    Ideal For

    Up to 15 people

    Includes

    Guide, Freedom Trail stops

    Highlights

    Trace Boston's revolutionary history through stories shared by a longtime resident and passionate historian. Step into historic Little Italy and take free time for lunch along the way.

    • Explore all 16 Freedom Trail stops, from Boston Common and the Old State House to the USS Constitution
    • Discover historic Little Italy on a detour from the Freedom Trail
    • Listen to stories from Boston's past shared by a former city employee
    • Enjoy free time for lunch at an artisanal farm-to-table market or America's oldest restaurant

    What's Included

    • Tour guide services

    Important details

    • Expect a walking-only tour with no vehicle transportation
    • Bring comfortable clothes and shoes

    Cancellation Policy

    Full refund when you cancel at least 14 days before the tour. Receive a 50% refund when you cancel at least 7 days before the tour. No refunds within 7 days of the tour.

    Product ID: EX57JW

    FAQs

    You do the entire experience on foot. This is a walking-only tour with no vehicle.

    You can bring up to 15 people on the private walking tour.

    Your booking includes tour guide services only.

    Meeting details

    Parkman Plaza, 139 Tremont St, Boston, MA 02111

    Experience provided by Boston Hidden Gems

    Related locations

    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 1-877-GREET-WELL

    Report an issue

    Large Private Group

    $610.50

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

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      Real humans ready to help with timing, questions, or special requests

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      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    682 reviews•Google Maps
    470
    15
    1
    0
    1

    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 4
    5/5

    Jenny is an amazing guide! Had a great time.

    Photo of Steven Hooper

    Steven Hooper

    September 1, 2026

    Review 1 of 1
    5/5

    Jenny is an amazing guide! Had a great time.

    Photo of Steven Hooper

    Steven Hooper

    September 1, 2026

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