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Top of the Hub...
I haven't tried this myself, but a knowledgeable person once suggested going to the restaurant at the top of the Prudential Tower, just for a drink at the bar. Supposedly it's cheaper than admission to the observation deck.
It is cheaper
or you can get tea, cheaper yet. I often take out of town guests there for the view.
Beer, anyone?
Go to Top of the Hub (Pru), have a beer and enjoy the view (b/c from there you can't see the Pru!)
Tufts library roof in Medford
is an outdoor deck on top of a building built into a hill. Walk onto it from the main quad; you don't go into the library building. Since it's an outdoor place, it's always open.
This is too far away from the
This is too far away from the city to provide a great view. Excellent place to smoke pot though
I second
Park at the top of Summit Ave., Brookline, right by Coolidge Corner.
For outside
For outside
Summit Street between Brookline and Brighton - nice little park at, well... the summit has a nice view.
Another nice view I stumbled across - go to the north/northwest area of the ring of Grampian Way (walking distance from Savin Hill Red Line station)
The Custom House Tower
is not free, but it's pretty cheap. And you get to look at the inner workings of the clock!
Falcons
You may also see falcons roosting on the tower.
Top floors
of BU's Mugar Library, especially some of the back stairwells.
But a) you have to BE QUIET and b) I'm not sure if the construction of the new buildings over by the Law school have blocked the view, since I haven't been up there since I was a wee undergrad.
Mass Eye and Ear, and Yawkey
Mass Eye and Ear, and Yawkey at MGH are good if you want to see the Charles or Beacon Hill.
Mass Eye & Ear cafeteria
is open to the public, and is located on the 7th floor, overlooking the Charles River.
East Boston
Madonna Queen of the Universe Shrine at Orient Heights has great views of the harbor and city. Bonus giant statue of the virgin. Free and easy to walk to from the blue line.
Mount Auburn Cemetery
For a view from outside the City of the skyline, check out the tower at Mount Auburn Cemetery in Cambridge. Beautiful 360 views of downtown Boston, Cambridge, Watertown, Belmont, etc.
The Bunker Hill Monument now
The Bunker Hill Monument now requires a free climbing pass from April through June, which you get at the museum at the base, to limit the number of people. I don't know how hard it is to get one at peak times.