Dinner at Field & Vine (Somerville), Dear Annie (Cambridge), or Tonino (Jamaica Plain). Beacon Hill Books and waitlist for a table for breakfast or lunch, or you can get coffee takeaway. If you want to grab some cheese, wine, or yummy fancy snacks head to Formaggio Kitchen. As for shopping, explore Back Bay, the South End, or any of the Squares in Cambridge/Somerville (you can get to these parts across the river by the red or green line trains).

So to be honest, I would not recommend eating in Quincy Market - it's not very clean and rats are abundant! (we live in a city, it's close to the water, so to be expected I suppose). If you like beer Sam Adams has a tap room right nearby.

For the North End, if you love seafood you have to eat at Neptune Oyster (for a fancy dinner). Get there early, put your name down if it's super busy, and go wander over to another bar or restaurant on Salem St. or Hanover St. to wait for your table at Neptune's (they'll call you). For a more casual and also incredibly delicious fresh seafood dinner, eat at The Daily Catch - their squid ink pasta is THE BEST. For desserts, I, someone who is part Sicilian, believe the best desserts are at Modern Pastry (they have coffee and drinks too, and a bar downstairs). There are also delicious coffee drinks and cocktails at Caffe Vittoria.

Ok this just took me like 20min to write and I have to start working now, haha - have an amazing trip!!