What should I avoid in Boston?

Quincy Market at Faneuil Hall looks like a food hall but operates like an airport terminal. You'll pay $22 for a lobster roll that's 60% bread, eaten standing up in a crowd that smells like old fryer oil and damp stone. The lobster roll worth eating is at Neptune Oyster on Salem Street in the North End, where a cold roll runs about $34 but fills both hands. That said, Neptune's line starts forming around 11am on weekends, so aim for a Tuesday. The Cheers bar at 84 Beacon Street sells the nostalgia hard, but the interior was never used in the show. The set was built in Hollywood. You'll pay $16 for a beer in a basement that feels like a theme restaurant in an airport Marriott. Mike's Pastry on Hanover Street pulls a line that wraps past the doorway most evenings. Modern Pastry, half a block south at 257 Hanover, makes cannoli that are, to be fair, better. Ricotta-filled, thinner shell, no wait. A cannoli at Modern costs $4.50 and comes out of the case in 30 seconds.

Do not rent a car. Boston's street layout predates the grid system by about 200 years. Roads that were cow paths in the 1630s still curve without warning, and the Central Artery tunnel system, which locals call the Big Dig, will route you onto I-93 South when you wanted Storrow Drive. Parking in Back Bay runs $40-55 per day at a garage, and the North End has roughly zero public spaces on weekends. The T, Boston's subway since 1897, costs $2.40 per ride on a CharlieCard. The Green Line runs above ground past Fenway Park. The Blue Line connects Logan Airport to downtown Aquarium station in about 12 minutes. You might notice the T shuts down around 12:30am, which is early by most city standards. If you're out past midnight in Cambridge, budget $15-20 for a rideshare back to downtown.

July and August in Boston feel nothing like the mild spring weather that travel photos suggest. Humidity sits around 65-75% through summer, and the brick sidewalks along Beacon Hill hold heat like a kiln by mid-afternoon. You'll feel the warm, wet air the moment you step off the T at Park Street station. Winters are the opposite problem. January temperatures drop to -7°C, and the wind off Boston Harbor cuts through anything thinner than a proper wool coat. Nor'easters between December and March can dump 30-50cm of snow in a single storm, shutting down the T's above-ground Green Line segments for hours. Spring is the wildcard. Marathon Monday in mid-April can swing from 5°C to 22°C in the same week. Pack layers and shoes with actual tread if you plan to walk the Freedom Trail, which was laid out in 1951 across 4km of brick and cobblestone that turns slick in any rain.

The Duck Boats are Boston's most oversold attraction. You'll pay $49 per adult for 80 minutes, 25 of which are spent on the Charles River in a retrofitted WWII amphibious vehicle that smells like diesel and mildew. The narration is scripted jokes, not history. You'll see the same buildings you walked past for free along the Freedom Trail, but from a less interesting angle. Worth noting, the harbor cruises from Long Wharf run about $25 and give you open water, the full skyline from the harbor side, and the salt air off Massachusetts Bay. Skip the CityPASS bundle math. It ties together the New England Aquarium, the Museum of Science, and the Museum of Fine Arts, which opened in 1870. If you're visiting fewer than 3 of those, individual tickets cost less. The Prudential Center Skywalk closed permanently in 2020. Some guidebooks still list it.