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Ugh, I hate Boston. But if you MUST go, most of the touristy things are centrally located in the Downtown area. Here is my list:
-Walk the Boston Common
-Visit whatever the name of that old church and cemetery by the Park Street station
-Walk up Charles Street to experience Beacon Hill
-Walk up Tremont St toward Government Center to see ugly City Hall but also Faneuil Hall
-The freedom trail is clearly marked on the sidewalks in this area as well
-Skip everything else and go to the South Boston Waterfront/Seaport
-VISIT THE ICA
-Go to Longwood and do the following:
—Visit the MFA and Gardener Museum
—Walk the Harvard Med School campus and look at the oldest public high school in the country next to it on Ave Louis Pasteur
—Walk the Fenway
All this, plus walk along the Charles River and take in the view. On both Boston and Cambridge sides. And in Cambridge, Harvard square is nice to walk around.
What are you into? Sports/museums/history? Also, what kind of food? Actually - regardless of what type of food, I will highly suggest you skip Top of The Hub - most overrated, touristy, restaurant you can go to. You’re paying for the view because the food is cafeteria quality just plated nicely. And you dont always even get the view.
Pomodoro in North End (call for res and bring cash), tea at Boston Public Library in Back Bay
Lolita Back Bay is a fun gothic mexican restaurant! For sightseeing, lots in the post above
If you want dessert in the North End, Mikes Pastry Shop or Modern Pastry Shop can’t be beat. I’m a big fan of the cannoli.
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I actually like signing up for the hop on hop off bus tours. It helps you cover a lot of ground.
The Boston one goes over to MIT and through many sections of town. I bought a two day pass, and definitely got my money’s worth. Used the bus vs Uber because they ran pretty frequently.
Harpoon Brewery
Eh, I’ve been turned off from them ever since they treated their employees like shit in opening the seaport venture.
If you are a history buff, actually go into Faneuil Hall (not the food court) and hear a brief overview from the National Park Service. Also visit Old North Church and Paul Revere house, both in North End and walkable from Faneuil Hall.