Boston in 1 Day for Families - Meet at City Hall Plaza next to Five Iron Golf for an easy, central start
In Collaboration with The Revolutionary Story Tour. Updated on January 31, 2026.
A 3.5-hour, family-friendly walking masterclass through Boston's original neighborhoods. Expert guide, small groups, built-in Quincy Market break, and a North End finish with a fun 'surprise' tea/ treat. Designed for families (strollers welcome) with frequent stops, short walks between sights, and kid-friendly commentary.
This itinerary was created in collaboration with The Revolutionary Story Tour, inspired by the tour The Full Revolutionary Story Epic Small Group Boston Walking Tour. Please check the tour information during your booking process.
Highlights
- Meet at City Hall Plaza next to Five Iron Golf for an easy, central start
- Visit 14 iconic Freedom Trail landmarks in the order history unfolded
- Built-in 15-minute Quincy Market break with family-friendly food options
- Paul Revere and Old North Church stories told in a lively, kid-appropriate way
- Finish in the North End near Lewis Wharf with a harbor-side surprise treat
Itinerary
Day 1
Summer small-group family walking tour covering core Freedom Trail sites with regular rest breaks and a Quincy Market pause. Start 10:30 AM, finish ~2:00 PM in the North End.
Meet: City Hall Plaza — gather next to Five Iron Golf
Group meeting and quick orientation. Guide will stand by the seasonal beer garden and the large BOSTON sign (great group photo opportunity).
Tips from local experts:
- Bring a lightweight stroller — City Hall Plaza is pedestrian-only and flat for easy parking/toy strollers.
- Use the plaza public restrooms inside nearby City Hall if someone needs one before we set off.
- Take a quick group photo with the BOSTON sign — it's shaded in the morning and makes a great memory for kids.
Boston City Hall — unusual architecture & big-picture intro
Short talk about Boston's modern civic life and how the old and new connect — kid-friendly stories about the city's character.
Tips from local experts:
- Point out the building's bold shapes to younger kids — it often helps them stay engaged.
- There are benches nearby for quick rest stops if small legs need a break.
- If weather is warm, this shady spot is a good place to reapply sunscreen before longer walking stretches.
King's Chapel area — the Puritans & early settlers
Family-friendly storytelling about the first Anglican congregation in Boston and life in early colonial times.
Tips from local experts:
- The sidewalks here are wide — good for strollers and letting children walk a bit while supervised.
- Mention brief, fun facts (e.g., unusual Puritan laws) to keep younger kids amused.
- If anyone needs a restroom, nearby options include the Park Street area; keep quick snacks handy for toddlers.
Park Street Church & Granary Burying Ground — tombs of patriots
Visit the 'brimstone corner' and Granary Burying Ground to see tombs of Paul Revere, John Hancock, and Sam Adams — told with age-appropriate anecdotes.
Tips from local experts:
- Keep voices low and explain cemetery etiquette to older children before entering.
- Granary has flat paths for strollers but some gravestones and curbs are uneven — fold strollers if you need to get closer.
- Share a 1–2 minute 'kid version' story of each patriot to make the visit memorable without long lectures.
Old State House & Boston Massacre site — where politics ignited
Short engaging recap of how colonial protests grew; visual storytelling and questions to keep kids involved.
Tips from local experts:
- Stand at the Massacre site markers — they're outdoors, so hats and water are helpful in summer.
- The plaza near the Old State House has space for kids to move around safely while the guide talks.
- Point out nearby shaded seating for caregivers while children hear a condensed story.
Old South Meeting House — democracy and lively public talk
Discuss the role of public assemblies in the road to revolution — short, interactive Q&A for kids.
Tips from local experts:
- This stop is short and interactive — prepare a simple question to ask kids (e.g., 'What would you do to make a change?').
- There are indoor restrooms nearby at Faneuil Hall/Quincy Market if needed.
- If someone in the group has a stroller, this stop is nearby the Quincy Market cluster so you can consolidate gear.
Quincy Market / Faneuil Hall — 15-minute family break
Built-in snack/restroom break at Quincy Market — many stalls, kid menus, high chairs available at nearby eateries.
Tips from local experts:
- Recommended family picks: lobster rolls (shared), clam chowder, and quick sandwiches — many vendors offer kid- sized portions.
- Public restrooms and a nursing room are located inside Faneuil Hall/Quincy Market (helpful for infants/toddlers).
- Avoid peak indoor lines by splitting your group: one adult in line for food while another watches kids at a shaded table.
Post Office Square & Washington St — authors, commerce, and city life
Quick walk-through highlighting historic publishing sites and how Boston shaped American letters — short stops to stretch legs.
Tips from local experts:
- Post Office Square has a small park area — perfect for a 2–3 minute runaround for kids.
- Benches and shade make this a comfortable spot for caregivers to rest while children snack.
- If anyone needs to step away from the group, cell reception is reliable here — set a simple rendezvous point.
Paul Revere Mall & Paul Revere House area — meet the midnight rider
Visit Paul Revere Mall (statues/reliefs) and overview of Paul Revere's House — family-friendly retelling of the midnight ride.
Tips from local experts:
- Paul Revere Mall is stroller-friendly and has a paved path — good for a quick photo and story moment.
- If lines gather for Paul Revere House photos, the guide uses short storytelling to keep kids engaged without waiting.
- Bring a small pair of binoculars for kids to scan rooftops — makes the midnight ride story more interactive.
Old North Church — 'One if by land, two if by sea' explained
Visit the famous steeple and hear a lively enactment for kids of the lantern signal and Paul Revere's ride.
Tips from local experts:
- Old North Church has a small entry fee if you choose to go inside; exterior storytelling is excellent and faster for families.
- Steeple views are fantastic from the square — there's room for strollers but prepare to fold if you need to get close to steps.
- Keep younger children engaged with a short 'treasure hunt' (spot the lanterns or look for a ship in the harbor).
Copp's Hill Burying Ground — harbor views & USS Constitution across the water
See the second-oldest burying ground and enjoy terrace views toward Charlestown and Old Ironsides; we view but do not board the ship.
Tips from local experts:
- The terrace across from Copp's Hill offers safer, flat viewpoints for strollers and excellent photo ops of the harbor.
- Bring a light jacket — summer harbor breezes can be cool on the terrace even on warm days.
- Point out the USS Constitution across the river as a visual 'connection' to naval history — kids love the idea of a real ship.
Bunker Hill Monument — dramatic recounting of the big battle (overview/recreation)
A spirited, family-appropriate recreation of the Battle of Bunker Hill and its significance — we summarize at Monument Square.
Tips from local experts:
- This stop includes some standing; children can sit on low walls nearby if available — comfortable shoes recommended.
- If small children can’t manage stairs, enjoy the monument from Monument Square and focus on the dramatic storytelling.
- Carry water and a small snack for kids — the energy of this segment often sparks lots of questions and running-around afterwards.
Harborwalk stroll — ocean breezes, piers & kid-friendly sightseeing
Leisurely walk along the Harborwalk for great views of Boston Harbor and to transition back toward the North End.
Tips from local experts:
- Stroller-friendly paths make this an easy, calming walk after the excitement at Bunker Hill.
- Keep small life-jackets or a secure stroller strap if you have curious children near the water’s edge.
- Look for small public playgrounds or benches along the Harborwalk for short rest stops.
Finish in the North End / Lewis Wharf — surprise family tea/treat & wrap-up
Wrap-up on Lewis Wharf in the North End with a 'surprise' tea-party style treat (cannoli or kid-friendly snack), final Q&A, and directions back to transit or meeting point.
Tips from local experts:
- For authentic cannoli, try Modern Pastry or a smaller local bakery if lines are long — guide will recommend the fastest kid-friendly option.
- Public restrooms and changing tables are available nearby; Lewis Wharf has convenient access to public transport for tired families.
- If you'd like a sit-down meal after the tour, the guide can point out family-friendly restaurants with kids' menus less than a 5-minute walk away.
Itinerary Attributes
| Days | 1 |
| Highlights | 5 |
| Season | - |
| Month | - |
| Persona | Families |
| Transfers | - |
| Restaurants | 1 |
| Total Activities | 14 |
| Total Places | 14 |
| Activities Types | Neighborhood, Attraction, Culture, Break, Outdoor, Meal |
