What should I avoid in Boston?

Don't rent a car for a trip that stays in Boston. Hotels in Back Bay and the Seaport often charge $50 or more a night for parking, the Ted Williams and Sumner tunnels charge tolls, and the roads around Leverett Circle confuse people who drive there every day. At Logan, follow the signs for the SL1 Silver Line, which has been free from the airport terminals since 2022 and reaches South Station in about 25 minutes. If you're staying in the North End or Beacon Hill, take the free Massport shuttle to Airport station on the Blue Line. MBTA fare gates now take a tap from a contactless bank card, so you don't need to queue for a CharlieCard. The Green Line catches a lot of first-timers: westbound trains split into the B, C, D and E branches at Copley and Kenmore, and the letter is printed small on the front of the car. The E branch is the one for the Museum of Fine Arts and the Isabella Stewart Gardner Museum. Get on a B by mistake and you'll rattle past Boston University for 30 minutes before you notice.

Quincy Market at Faneuil Hall is where most visitors eat their first meal, and it is often the worst one of the trip. The food court under the colonnade smells of fryer oil, and a bread-bowl chowder there costs about twice what it's worth. Boston Public Market at 100 Hanover Street is a 3-minute walk away, and its indoor stalls sell Massachusetts oysters, warm cider donuts and lobster rolls from New England producers. Skip the Cheers bar at 84 Beacon Street as well: the outside matches the opening credits of the show, but the cramped basement room looks nothing like the set, and the burgers come at tourist prices. In the North End, the line at Mike's Pastry, 300 Hanover Street, can run 30 minutes on a Saturday afternoon. Modern Pastry, across the street at 257 Hanover, fills its cannoli when you order, which keeps the shell crisp and the ricotta cold and faintly sweet.

The Freedom Trail runs 2.5 miles of red brick from Boston Common to the Bunker Hill Monument in Charlestown, and with 16 stops along the way most people need about 4 hours. Don't attempt the whole thing on the day you arrive. On a jet-lagged first afternoon, walk from the Common as far as the Paul Revere House and the Old North Church, then have dinner in the North End. Save Charlestown and the 294 steps up the Bunker Hill Monument for day two. On game nights at Fenway Park, ignore the men holding up tickets on Lansdowne Street and Brookline Avenue. Fake and already-scanned tickets surface every season, and the guaranteed options are the MLB Ballpark app and the Red Sox's official resale market. For 45 minutes after the last out, Kenmore station is packed and smells of damp wool and spilled beer, so walk the 15 minutes to Hynes Convention Center station or catch the D branch at Fenway station.

Don't underdress. On the afternoon of 18 October 2026 it was 11.5°C under a clear sky, but the wind off Boston Harbor made it feel like 8.9°C, and Long Wharf and the Seaport waterfront feel colder still. Pack a windproof layer for any trip from October on. Between December and March, a nor'easter can drop a foot of snow overnight and slow the T for a day. The brick sidewalks on Beacon Hill's Acorn Street and Mount Vernon Street turn to sheet ice, so bring shoes with real grip. Hotel prices jump on Marathon Monday in April, during college graduation weekends in May, and over Head of the Charles Regatta weekend in October; for those dates, book at least 3 months ahead.