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    5. Explore Boston Freedom Trail & Little Italy Private Tour
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    Explore Boston Freedom Trail & Little Italy Private Tour

    Walk all 16 Freedom Trail stops with a private guide plus a detour through Little Italy

    5.0 stars• 471 reviews
    From$654incl. taxes and fees

    Duration

    4 hour 30 min

    Ideal For

    Up to 15 people

    Includes

    Guide services, Free time

    Highlights

    Explore Boston’s Freedom Trail on a private, walking-only tour led by a longtime resident and passionate historian. Cover all 16 stops, then detour through historic Little Italy with free time for lunch.

    • Walk all 16 stops on the Freedom Trail
    • Discover sites like Paul Revere House, Old North Church, and Bunker Hill Monument
    • Visit USS Constitution and other historic landmarks
    • Detour through historic Little Italy
    • Start at the Boston Common Visitor Center
    • Plan for optional gratuities and clarify the amount with Greetwell before booking

    What's Included

    • Tour guide services

    Cancellation Policy

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

    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

    Boston Common Visitor Center (139 Tremont St., Boston)

    Experience provided by Boston Hidden Gems
    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 (650) 414-7338

    Report an issue

    Reference #EX57JW

    Large Private Group

    $654.23

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

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

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    471 reviews•Google Maps

    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

    We had a great time on our full day Lexington and Concord tour. Our guide Jenny was a joy to listen to. Loved all the information she shared. Learned a ton of history. Thought the tour was a great pace and enjoyed all the places we went.

    Photo of Adrienne Gibson

    Adrienne Gibson

    March 17, 2026

    Review 1 of 1
    5/5

    We had a great time on our full day Lexington and Concord tour. Our guide Jenny was a joy to listen to. Loved all the information she shared. Learned a ton of history. Thought the tour was a great pace and enjoyed all the places we went.

    Photo of Adrienne Gibson

    Adrienne Gibson

    March 17, 2026

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