Boston, Massachusetts

Boston is a compact city of about 685,000 people on the Massachusetts coast, with a walkable downtown that manages to contain an unusual density of American history, university infrastructure, and very good seafood. It is also stubborn about certain things: the streets do not follow a grid, parking is genuinely terrible, and Bostonians walk across intersections when they choose rather than when the signal says. The most walkable big city in the United States is the claim, and it is probably accurate.

2026 note: Boston hosts seven FIFA World Cup matches at Gillette Stadium in Foxboro from June through July. Hotel availability and prices across the city will be significantly affected on those dates; book far ahead or adjust timing.

The Freedom Trail

The Freedom Trail is a 2.5-mile marked walking route connecting 16 sites related to the American Revolution, from Boston Common through the North End to the Charlestown Navy Yard. The trail is marked by a red line (painted or brick) on the sidewalk. Sites include Paul Revere’s House (the oldest remaining structure in downtown Boston, built around 1680), the Old North Church where lanterns were hung to signal the British advance in 1775, and the USS Constitution – the oldest commissioned warship afloat – moored at the Charlestown Navy Yard.

The whole trail takes three to four hours; guided tours depart from the Visitor Center on Tremont Street. Most sites are free or charge minimal entry.

Beacon Hill and Back Bay

Beacon Hill, immediately north of Boston Common, is a neighbourhood of Federal-period townhouses on narrow gaslit streets. Charles Street at the base of the hill has independent shops and restaurants. Acorn Street, off Willow Street, is the most photographed cobblestone alley in Boston – worth seeing but genuinely short.

Back Bay, laid out on filled land in the 19th century, has Commonwealth Avenue’s formal brownstones, the Public Garden, and Newbury Street’s cafes and retail. The Isabella Stewart Gardner Museum in the Fenway (about 15 minutes from Back Bay) contains an exceptional private collection in a Venetian palazzo-style building, arranged by Gardner’s explicit instructions unchanged since her death in 1924. Considerably less visited than the Museum of Fine Arts next door and arguably more interesting.

Food

Clam chowder, lobster rolls, and oysters are the culinary identity. Legal Sea Foods is the reliable local chain for chowder (about $8 for a cup). For lobster rolls, Neptune Oyster in the North End has a consistent reputation with a persistent wait; Row 34 in the Fort Point Channel neighbourhood has similar quality and more space. Cannoli from Mike’s Pastry on Hanover Street in the North End is a North End obligation; the line moves quickly.

For a proper dinner: the South End has the highest density of serious restaurants. Toro on Washington Street (Spanish tapas, reservations essential) and Coppa on Shawmut Street are two consistently strong options.

Getting Around

The T (subway) covers downtown, Back Bay, Cambridge (Harvard and MIT), and the airport. Since January 2025, contactless credit card payment works on all MBTA lines without requiring a CharlieCard. A single fare is $2.40. A 7-day LinkPass costs $23 and breaks even after 10 trips. The Silver Line SL1 runs from South Station to Logan Airport for the subway fare.

Amtrak’s Acela connects Boston South Station to New York Penn Station in about 3.5 hours and costs $80-180 depending on booking. The regional rail to Providence takes under an hour.