Shopping in Boston generally revolves around four spots: Downtown Crossing, Copley Square, Newbury Street, and Faneuil Hall.

In the Downtown Crossing area, you will find the department store giant Macy’s (formerly Jordan Marsh). The once-famous Filene's has been purchased by Macy's and has now been taken over by the chain. The bargain hunter’s paradise Filene’s Basement, made famous by its automatic markdown system and no-holds-bar bi-annual wedding dress sales, is a completely separate company from Filene's and thus was not directly affected by the Filene's sale and closure. However, in September of 2007 the original location of Filene's Basement in Downtown Crossing closed for a couple of years to accommodate a major redevelopment of the Filene's building above.  (See the Newbury Street paragraph below for information an alternative Filene's Basement location.)  Also in the Downtown Crossing area, you can find a DSW Shoe Warehouse, a TJ Maxx Marshalls, and an H&M in addition to other smaller stores.  There are a few higher end stores in the area servicing the workers in the nearby financial district, like Thomas Pink, Johnston & Murphy, and Talbots. Don't forget to check out Boston's diamond district, a building of jewelers and diamond merchants selling at wholesale prices.  It can be found at 387 Washington Street beside DSW Shoe Warehouse.

Just a couple of blocks away, Faneuil Hall is, without question, a favorite shopping destination for several reasons.  First, it has the customary collection of chain stores for mall type buying -- Banana Republic, Gap, American Eagle, Victoria's Secret, Ann Taylor, Ann Taylor Loft, Coach, Swatch, April Cornell, FunUsual, Godiva, Nine West, Bostonian, and more, including stores that sell all things Boston (great if you need to pick up a souvenir for that special someone). It also has a multitude of dining options.  You can opt for a more formal meal at the Rustic Kitchen or McCormick and Shmick's or try Indian, Irish, or Iitalian food at the extensive food court.  There are many informal dining options -- pretzels, salads, meats, ice cream, smoothies, sushi, etc. in the centrally located Market Building.  If these dining options are not enough, the North End with its fabulous Italian food is only 5 minutes away.  In addition to the shopping and the dining, in the summer crowds often gather at Faneuil Hall to watch comedians, jugglers, dancers, and clowns.  Finally, it is just a great place to stroll through any time of the year.

Many have called Newbury Street Boston’s Rodeo Drive. Newbury Street’s eight cross streets are alphabetical, from Arlington to Hereford, so it’s comparatively easy to know where you are. Lined with boutique shops and designer stores, Newbury Street is a good place to walk around and spend lots of money in a short period of time. It is worth noting that, in addition to these designer stores like Chanel, Louis Boston, and Armani; there are plenty of "affordable" shopping sites like the Gap, Banana Republic, and Pottery Barn. Aside from shopping, you will find some of Boston’s most interesting people-watching on Newbury Street as well. In the summer, enjoy a shopping break at one of the many restaurants with outdoor or sidewalk seating. A second Boston Filene's Basement is now in this area (Back Bay), with store entrances on both Newbury Street and Boylston Street in the block between Berkeley and Clarendon.  It is tonier and more organized than the no-frills original location, but it does not have the original's famous Automatic Markdown Policy. Just one street off of Newbury, Copley Square is also a great shopping area thanks to the Copley Place Mall and the Prudential Center, two interconnected malls that have both the standard commercial chain stores like the Gap, J.Jill, Express, Banana Republic, and Victoria’s Secret and high end stores like Gucci, Louis Vuitton, Christian Dior, Tiffany’s, Saks Fifth Avenue, and Neiman Marcus.  Prudential Center has kiosks that sell a wide range of items, from the latest Hello Kitty accessories to Harvard logo attire, as well as a roomy food court with lots of fast food dining options when you are ready to take a little time out from shopping. 

Charles Street in Beacon Hill is smaller than any of these areas, but offers an interesting mix of antique shops, boutiques and restaurants.  Well worth a stroll, though the prices can be steep. This short walk will give you a sense of Boston's architecture and history as you browse in interesting shops.

Venture a little further afield and head on foot over to the South End. Here you'll find small designer boutiques with one-of-a- kind finds in the midst of great old brownstone architecture from a century and more ago.

Just out of town, in Chestnut Hill and Newton, very near Western suburbs accessible by MBTA on the Green Line (Riverside), you can find high-end shops (Chestnut Hill Mall, Atrium Mall) and innovative, stylish designer shops (Newton Center, opposite the Green Line MBTA station).  There are also several high end boutiques in Wellesley Square (commuter rail stop on the Worcester/Framingham line).