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$654incl. taxes and fees
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Discover what we've curated for you
See all 16 Freedom Trail sites and Little Italy with a private guide in 4.5 hours
Discover what we've curated for you
4 hour 30 min
Up to 15 people
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.
This is a walking-only tour with no vehicle. Maximum 15 people per tour. Tour starts at Boston Common Visitor Center.
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.
Tour starts at Boston Common Visitor Center (139 Tremont St., Boston)
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.
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.
Adrienne Gibson
March 17, 2026
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.
Adrienne Gibson
March 17, 2026