Whether your vacationing party is made up of swill-guzzling extroverts, history and art buffs, or any type in between, grabbing a cheap flight to Boston is sure to exceed everyone's expectations. Founded over a hundred years before American independence, Boston is teeming with historical sites like Battle Road and Paul Revere's house. For the squeeze-everything-in-over-the-weekend vacationer, the Freedom Trail is the best way to hit every major spot within two hours. Marked by red paint, the three-mile journey connects 16 of Boston's most historical sites from the Boston Common to Faneuil Hall and the site of the Boston Massacre. Many art aficionados book their Boston flights just to visit the 236-year-old Museum of Fine Arts, which is hailed as the best collection of early American and Impressionist art. Even an aimless schlep through the streets proves entertaining as you try to blend in amidst throngs of busy Bostonians, because you never know when a street performer will set up shop and ask for volunteers.
For more brew-inclined travelers, there are dozens of historic bars and taverns, many proudly featuring “Boston's best microbrew,” placed just a few sneaky steps away from most tour group routes. Some would argue that a flight to Boston is wasted without a drink at Green Dragon Tavern, founded in 1654. The oldest bar in Boston, Green Dragon was the unofficial meeting place of such men as Paul Revere, Joseph Warren and Samuel Adams. Even the cheapest of cheap flights to Boston are also wasted without a trip to Warren Tavern, which was the first building built after the British destroyed Charlestown in the Battle of Bunker Hill.