Boston itinerary for first-timers
The classic neighborhoods in an order that works, with a 4K street walk for every stop. Watch your trip before you take it.
Day 1: The Freedom Trail & the North End
Follow the red line from Boston Common past the Old State House and Faneuil Hall into the North End, then walk the waterfront at night.
- 1
Morning
Boston Common & the Freedom Trail
America's oldest public park is the start of the Freedom Trail. Follow the red line past Park Street Church, the Granary Burying Ground, King's Chapel and the Old South Meeting House, where the Boston Tea Party began.
- Boston Common
- Park Street Church
- Granary Burying Ground
- King's Chapel
- Old South Meeting House
The trail is about 2.5 miles end to end; the red line in the sidewalk makes it easy to follow on your own.
Follow the Freedom Trail down School and Washington Streets, about 15 min.
- 2
Midday
Old State House & Faneuil Hall
The Old State House, where the Declaration of Independence was read to Bostonians, stands above the site of the Boston Massacre. A few steps on, Faneuil Hall and Quincy Market have been meeting places and markets since the 1700s.
- Old State House
- Boston Massacre site
- Faneuil Hall
- Quincy Market
Cross the Rose Kennedy Greenway to Hanover Street, about 5 min.
- 3
Afternoon
The North End
Boston's Little Italy and its oldest neighbourhood: narrow streets of cafés and bakeries, the Paul Revere House, Paul Revere Mall and the Old North Church, where lanterns warned that British troops were on the move in 1775.
- Hanover Street
- Paul Revere House
- Old North Church
- Copp's Hill Burying Ground
Walk down to the harbour, about 10 min.
- 4
Evening
The waterfront at night
Walk down to the harbour as the lights come on: the waterfront park, Long Wharf and back past a lit-up Faneuil Hall.
- Christopher Columbus Waterfront Park
- Long Wharf
- Faneuil Hall at night
Day 2: Beacon Hill, Back Bay & Fenway
The Public Garden and Acorn Street in the morning, Copley Square and Newbury Street, then Fenway Park.
- 1
Morning
Public Garden & Beacon Hill
The Public Garden's lagoon and willows lead up to Beacon Hill, with gas lamps, brick sidewalks and Acorn Street, a cobbled lane that is one of the most photographed streets in the country.
- Public Garden
- Acorn Street
- Beacon Hill row houses
- Boston Common
Go early to have Acorn Street to yourself.
Morning Walk through the Public Garden & Beacon Hill
Video by Numinous Walks on YouTube
Walk along Commonwealth Avenue or Newbury Street, about 15 min.
- 2
Late morning
Back Bay: Copley Square & Newbury Street
Copley Square with Trinity Church and the Boston Public Library, then Newbury Street's eight blocks of brownstones, boutiques and cafés, and back along Boylston Street.
- Copley Square
- Boston Public Library
- Newbury Street
- Boylston Street
Step inside the Boston Public Library's central building; its courtyard and reading room are free to visit.
Walk west along Boylston Street or take the Green Line, about 20 min.
- 3
Afternoon
Fenway Park
Home of the Red Sox since 1912 and the oldest ballpark in Major League Baseball. On game days the streets around it fill with fans, vendors and busy bars.
- Fenway Park
- Jersey Street
- Lansdowne Street
Fenway Game Day Walk
Video by OUT 4A WALK on YouTube
Day 3: The Seaport & downtown by night
The Harborwalk and the ICA in the Seaport, then Chinatown, Quincy Market and the waterfront after dark.
- 1
Morning
The Seaport & the ICA
Boston's newest district, built on old wharves: the Harborwalk along the water, the Institute of Contemporary Art leaning out over the harbour, and waterfront restaurants with views back to downtown.
- Harborwalk
- Institute of Contemporary Art
- Fort Point Channel
Walk back over the Fort Point Channel to Chinatown, about 20 min.
- 2
Evening
Chinatown & downtown at night
Start under Chinatown's gate and walk through the quiet downtown to Quincy Market and the waterfront, a calm way to end the trip.
- Chinatown gate
- Quincy Market
- Downtown at night
Travelling with someone?
Send them this 3-day Boston plan, videos included.
Planning your first trip to Boston
How many days?
Three days is a good first visit: the Freedom Trail and the North End, then Beacon Hill, Back Bay and Fenway, then the Seaport and the waterfront. One day covers the Freedom Trail.
Where to stay
Back Bay and the area around Boston Common are central and walkable; the North End and the waterfront are close to the Freedom Trail, and the Seaport is newer and modern.
Getting around
Walk almost everything. The T (subway) and buses cover longer hops, such as Fenway and the Seaport; the Green Line runs under Boylston Street towards Fenway.
Boston is one of the easiest American cities to see on foot. The Freedom Trail, a red line in the sidewalk, links the sites of the Revolution from Boston Common to the North End; around it, Beacon Hill's gas-lit lanes, the brownstones of Back Bay and the new waterfront of the Seaport are all within walking distance.
Every stop comes with a walking video filmed on those streets, so you can see the route before you arrive. Use the buttons under each video to jump to a landmark, or press Preview to watch a whole day in a row.
Boston itinerary: common questions
How many days do you need in Boston?
Two or three days is a good first visit: one for the Freedom Trail and the North End, one for Beacon Hill, Back Bay and Fenway, and a third for the Seaport and the waterfront.
Can you walk the Freedom Trail on your own?
Yes. A red line in the sidewalk links its 16 sites over about 2.5 miles, from Boston Common to Charlestown. Walking it with stops takes most of a day.
Is Boston a walkable city?
Very. The centre is compact, and Beacon Hill, Back Bay, the North End and the waterfront are all close together. The T covers longer distances, and winter sidewalks can be icy.
When is the best time to visit Boston?
Late spring and early autumn are the most pleasant; October brings fall colours. Summers are warm and busy, and winters are cold and often snowy.
Travel times are approximate. Check opening days and any booking requirements before you go.
Keep exploring Boston
More 4K walking videos, top sights, food markets and dishes to try.
Boston city guide →