This is my friend Bryce's guide. He breaks things down based on the area you are looking to visit. Has everything you need in one spot!
Good Italian food: La Famiglia Giorgio's (large portions!) Dessert: Bova's Bakery Pizza: The Original Regina Pizzeria (Sam's favorite pizza) Walk the Freedom Trail Relax at Boston Common + Boston Public Garden Explore the Seaport District Visit Faneuil Hall Marketplace See Fenway Park
Tour the waterfront mansions (including The Breakers) Walk the scenic Cliff Walk Explore the cute downtown shops + restaurants
Great hiking just a drive north with tons of trails and mountain views
Ice cream: Crescent Ridge Dairy (try graham central station) Pizza: Town Spa Pizza (classic bar-style pizza) Bagels: Life's a Bagel (Andy's favorite!) Anejo Mexican Bistro: Not the most convenient spot but a favorite for Sam and her friends (get the coconut margarita and birria quesadilla!) Breakfast: The Farmer's Daughter or Yaz's table (both can get really busy) Stone L'oven: Convenient spot that has everything from pizza, subs, salads and more