The North End is full of great restaurants and bakeries. We recommend a lobster roll from Neptune Oyster, pizza from Regina's, an Italian sub from Monica's, or a cannoli from Mike's Pastry. If you are looking for dinner, try Mama Maria or Al Dente.
There are lots of restaurants and stores in the Seaport. There are also two breweries, Harpoon and Trillium, and Legal Harborside is great for seafood.
Check out Harvard Square, where we spent a lot of time while John was finishing law school. You can walk through Harvard Yard, get a bagel at Bagelsaurus, or grab a drink at John Harvard's Brewery.
If you are looking to shop, try Newbury Street, Charles Street or the Copley Mall.