If you're looking for a vacation to an old-fashioned Christmas destination, Boston is a good bet. Seek out the colonial cobblestone streets bedecked with greenery and lights. While you're walking, you may encounter carolers serenading passers-by on Beacon Hill or one of the many impressively decorated trees at spots such as Macy's and Boston Common.
The Frog Pond at Boston Common is available for open-air skating from November through March. You may rent skates or bring your own; lessons are available through the Skating Club of Boston. Children under age 13 are free. The Frog Pond stays open well into the evening during the winter season, so you may enjoy the holiday lights on display throughout the city as you skate. Frog Pond is open on Christmas Eve but closed on Christmas Day.
Faneuil Hall has been standing on the Boston waterfront since 1742. It houses more than 70 retail and dining establishments, and hosts a plethora of renowned street performers. Shop for anything from cupcakes and candles to boutique clothing and body-care products. Faneuil Hall is open into the late evening hours. During the holiday season, Faneuil Hall puts up its own towering Christmas tree and offers a nightly LED light show. On Christmas Day, the stores are closed but the historic building itself is open and the light show is on full display.
Every afternoon during the holiday season, the historic Boston Harbor Hotel offers a formal tea service it calls the Holiday Frost-Tea at the Rowes Wharf. The menu of this child-friendly meal includes tea sandwiches, scones, holiday cookies, hot cocoa and an array of loose-leaf teas from which to choose. Reservations are required. Visitors are invited to the hotel's outdoor skating rink. On Christmas Eve and Christmas Day, the hotel also hosts a four-course dinner at the Meritage restaurant; Christmas Day also features brunch.
The Boston Pops favors a light-classical and popular-music repertoire. Every Christmas season, the Boston Pops performs its Holiday Pops show, which includes a sing-a-long portion as well as the requisite guest appearance by Santa. Tickets are in demand, so plan ahead accordingly.