Why go: Full of history and culture, Boston is in many ways our country’s first city– home to The USS Constitution, Fanueil Hall, The Old State House, and Harvard University. Also home to the oldest subway system in North America, which also happens to be America’s oldest light rail system.
Private Car parking in BOS: While rail cars often need to get parked in the coachyard on weeknights, it is possible at the option of the station master to have a private car parked in the station at a bumper post on weekend nights. Station parking is really enjoyable–you are less than 50 feet from the main waiting room, and a three minute walk from there to the station’s subway station.
Boston highlights for private car folks: If you’re working the trip, and doing a little provisioning, you can get to food stores on the Green Line, but may wind up calling a cab to get back to the station: Traveling West on the Beacon St. Green Line, there’s a Whole Foods Market near St. Mary Street. Ride a few more blocks and there’s a Trader Joe’s at Harvard Street. The nearest Grainger Supply is on Arsenal St in Watertown (take the #70 bus from the Subway Red Line Central Square station). If you’re sightseeing, public transit is great–a one day pass is $12 (seven-day pass is $19) and can be purchased at any subway station. Despite being the most northeastern terminus of the Amtrak’s Northeast corridor, due to the high speeds used on the NEC, there’s only two Amtrak trains that will move private cars in and out of Boston: Amtrak’s 448/449 (Boston section of the Lake Shore Limited) which connects via Albany, NY, or Amtrak’s 66/67 (Overnight NEC train), which will accept private cars in Washington, DC, but not New York. Amtrak’s car services includes water, dumping, and a car wash. Station crews are easy to work with, and very professional.
Other transportation: At the north end of Amtrak’s Northeast Corridor, there’s frequent service to New York, Washington and points south by train. Airport is accessible by the subway Blue Line, and also via the Silver Line (bus rapid transit) from an underground bus platform alongside South Station.
Anything else: In the last ten years, Boston has become chock-full of gentrified neighborhoods and wonderful restaurants. My favorite neighborhood strolls are long walks through Brookline and Cambridge, and I’ve spent some happy rainy days at the Gardner Museum, and at the Co-Op book store in Cambridge. Oh, and the beer: Boston is the home of Harpoon Brewing, which has great tours. Favorite local spots include Redbones in Somerville (Davis Square) and Deep Ellum, in Allston.