For Boston:
1. Red Sox Game. Fenway Park is amazing, and even if your wife isn't a sports-nut, she'll LOVE the atmosphere.
2. Samuel Adams Brewery Tour. Don't know if she's into this kind of thing, but I've been on a number of brewery/winery tours, and really enjoyed this one.
3. Hang out (picnic lunch?) down by the water. There a TON of small parks near the water. Commerce street offers plenty of options. Take a couple of beers or a bottle of wine, enjoy the sunshine and the view of the water.
4. Cheers. Ya, seriously. Pretty average bar, not nearly as many tourists as one would expect, and they really do have an amazing clam chowder.
5. Walk "The Freedom Trail". It's a (generally) beautiful walk, and will take you through Boston Common (gorgeous in the summer!!), Paul Revere's house, the Bunker Hill monument, Old North Church, etc. There are plenty of rest/eat/beer opportunities along the way, so the walk can last a whole afternoon if you want, despite only being ~4 or 5km. You ultimately end up at the old ship USS Constitution. No idea if that's a worthwhile tour....
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