Explore Boston's history beyond downtown with a private guide
5.5 hours
Up to 6 people
Private vehicle, guide, entry
Explore Boston's past with your private guide and hear stories that go beyond the standard history books. Shape the day around the places that interest your group.
30 min - Pick Up Your guide will pick you up in a comfortable minivan, as you begin your day in style!
30 min - Caffe Vittoria At the North End's oldest cafe, enjoy a beverage and a pastry while you learn about the North End through a series of maps and stories.
30 min - Paul Revere House Step inside downtown Boston's oldest building, the Paul Revere House, where his Midnight Ride began. Entry is included in your tour.
15 min - North Square See North Square, one of Boston's oldest public spaces. Explore the public artwork honoring the neighborhood's hisory!
10 min - Old North Church Admire Boston's oldest standing church from outside, where the famous signal lanterns were hung to warn of the British approach. Standing beneath the iconic steeple, hear how a young Paul Revere rang the church bells as a teenager and later organized the lantern signal that launched the midnight ride!
15 min - Copp's Hill Explore Copp's Hill burying ground, where many of our earliest settlers and some Revolutionaries are buried.
20 min - USS Constitution Stop by the world's oldest commissioned ship of war and learn about her construction, authorized by President George Washington.
20 min - Bunker Hill Monument See the obelisk and learn about one of the first major battles of the American Revolution
60 min - Break Take a break for lunch at a local artisanal market, with plenty of choices!
30 min - Boston Common Hear stories about the Pine Tree Riots, the founding of Boston, and the country's first football club!
20 min - Acorn St/Beacon Hill In one of America's most beautiful neighborhoods, stroll along the brick-laid streets and stop by the most photographed street in the country!
20 min - Public Garden In America's first botanical garden, learn about the (contested) discovery of anaesthesia, and Boston's infamous 4-time non-consecutive mayor.
30 min - Drop Off Your guide will drop you off back at your hotel, cruise ship, or airport!
Receive a full refund when you cancel at least 14 days before your tour. Receive a 50% refund when you cancel at least 7 days before your tour. No refunds within 7 days.
Wear comfortable clothes and shoes. Bring money for lunch and souvenirs.
No. The tour includes 1 hour of free time for lunch, and you pay for your own lunch.
No. Gratuities are not included.
Pickup at your hotel in Boston/Cambridge
Step inside The Paul Revere House and you are standing in the oldest surviving structure in downtown Boston. The low ceilings, wide-plank floors, and leaded windows transport you directly into the world of colonial New England. Built around 1680, The Paul Revere House is where the silversmith and patriot lived during his now-legendary midnight ride of 1775, and every room carries the quiet weight of that history.
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.
Jenny was super knowledgeable, flexible, and navigated our whole day professionally! On one of hottest days of the summer she made sure every group member had what they needed. Highly recommend!
Lynne Avdellas
July 3, 2026
Jenny was super knowledgeable, flexible, and navigated our whole day professionally! On one of hottest days of the summer she made sure every group member had what they needed. Highly recommend!
Lynne Avdellas
July 3, 2026
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