If you want the best view of Boston from around Boston, check out the Tavern at the Quarry Hill Golf Course in Quincy.
There's a patio near the bar so you can stare at the city at sunset. Only negative is the broadcast tower.
The old quarries played a pivotal role in The Departed, but you wouldn't recognize them from this place. A betting person would wager that some of Whitey Bulger's old buddies ended up in those holes.
The developers apparently cut a sweet deal to haul off Big Dig rubble to fill in some of the 26 granite quarries, leaving others intact. Rumor has it not only did they get the actual landfill free, they may have been paid to haul it away. Doubly sweet. The Tavern stands at the lip of one of the pits so you can stare out past that at the skyline.
My buddy spent his child hood sneaking into the old quarries and diving from ungodly heights. He said other kids did the same but didn't survive. His dad, the fire chief, had to fish people out all the time and promised hellfire if his kids were caught up there.
Funny thing, my buddy said, was all the kids he used to see there were sons of firemen and cops. "We all should've known better."