Winter sort of cuts the free stuff way down. In the summer, there are free concerts, movies, street performers at Faneuil Hall and Quincy Market, the parks are open, etc. You can take a ferry out to Georges Island (where there s a haunted Civil War fort) and other harbor islands, one with swimming. Winter everyone hunkers down inside. Free in winter:Bunker Hill MonumentUSS Constitution and the USS Cassin Young Boston Public LibraryState HouseFirst Night Boston on New Year s Eve. Many free events. http://www.firstnight.org/Low cost:Ice skating on the Frog Pond (Boston Common) Under 13 is free, $4 otherwise. (Plus skate rental if you need to.) http://www.bostoncommonfrogpond.org/hour��Get a digital camera and learn to take interesting photos of the city. (Cemetaries and statues look cool in the snow.) Festivals start in the spring. There s the Dragon Boat Festival, Lilac Sunday at the Arboretum, feasts in the North End, etc. Have your parents bring home an Improper Bostonian and a Boston Parent s Paper which both list events. Check Boston Central. http://www.bostoncentral.com/events.phpThe Museum of Fine Arts has a free weekend day every month. Check your local library for museum passes. (BEST deal around!) As an example, check out the ones at the Newton library: http://www.newtonfreelibrary.net/?sec=se��Cheap places to eat: Chinatown, Quincy Market Food Court, Prudential Food Court. Pizza, Mexican, Chinese, and Thai places are cheap. Anywhere students hang out has cheap food.
I don t know if you have to have a library card but the libraries have deeply discounted and free passes to tons of the museums, it s kind of a coupon but not really. You can pick them up at different branches and they have more info about it at the city of boston website.
Museums, lots of Museums: The MFA (art) Isabella Stuart Gardner (art) ICA (art) The Aquarium, The Science Museum, Harvard and MIT museums, not to mention all the Historical sites; sites along the Freedom Trail, John Adams HouseVisit the Harbor Islands, Blue Hills State reservationshopping, lots of shopping in Quincy Market, Newbury Street or Harvard Square in Cambridge, also visit the insanely overpriced Copley Place Mall (look, don t buy anything) Go to the top of the Prudential Tower for a great view