Hi Dawn, Here are some ideas
Boston north end
Italian restaurants and pizzerias:
Prezza, 24 Fleet St (617) 227-1577
Mamma Maria,
Pizzeria Regina,-Fabulous Pizza!!
Galleria Umberto,
Giacomo's,
**Antico Forno, 93 Salem St
Maurizio's,
Marco,
**Taranta, 210 Hanover St 617) 720-0052
Daily Catch,
Pagliuca's.
Also in the North end-Pastries at "Mike's pastry" 300 Hanover St, this is the fun one for sitting and people watching. But I think the best pastries are at "Modern Pastry" down the street at 257 Hanover.
For something fun, go to Chinatown, we like to stop at Eldo bakery (it's on Harrison Street), ask for the "Dahn Taht", they'll bring them out from behind the counter, still warm. They're a little 2 bite egg custard tart with a flaky crust.
Chinese restaurant-"Peach Farm"-is highly recommended (4 Tyler Street)
For fabulous lobster rolls and oysters and stuff like that, I HIGHLY recommend "B and G oysters" 550 Tremont.