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Sam Adams, Harpoon or another?

I liked the Sam Adams tour a lot. Don't know about Harpoon.
 
Skip harpoon tour, but do their flight and get some house made soft pretzels.

For good less known micros head to Cambridge area with several small breweries
 
When in Boston, which should I make sure to visit?

Probably Sam Adams. I'm not a fan of either quite frankly, they're both too mainstream and uninteresting for the most part. But I was just in Boston about a month and a half ago and we went to Harpoon that trip (Sam Adams was much more distant in time so I don't know what's changed). Harpoon was very meh as a brewery tour, it reminded me of the tour I took two weeks ago in Atlanta in Sweetwater. Very quick and uninformative with no real bells and whistles and no decent tasting before or after the tour (unless our dingbat coed hostess forgot). Sam Adams was a much more detailed and impressive tour. It wasn't one of my all time favorites (Yuengling in PA is by FAR the best brewery tour Ive been on and I've been on a LOT, they take you down into the cave system they used prior to air conditioning being invented and they kept up part of the brick walls that prohibition forces threw up to block off the caves so you can see that portion of history plus a ton of secret tunnels.). Sam Adams wasn't in my top five or ten brewery tours BUT it's better than most, a good B-. Harpoon was basically doing as little as they felt they could get away with in order to force you into their big barroom. So a C-, D+.

If you've got a car, Jack's Abby about 30 mins from Boston is supposed to be awesome (although I haven't been), friends who have compare it favorably to my favorite craft brewhouses Wicked Weed in NC and Victory in PA. And an hour away in Portsmouth and the surrounds you've got Redhook, Smuttynose, and Portsmouth Brewery. All of those are likely to be better than anything in Boston.

Having said that, if you're stuck in Boston I'd probably go with the stereotypical Sam Adams trip. It wasn't bad (again, it's been a few years for me) at all. Oh, and if you want to grab a historic pint, make sure you walk over to the Warren Tavern. It's a very short hike from Bunker/Breed's Hill Monument and is a Revolutionary-era tavern.
 
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