Prefer Boston proper and something fun or with bit of drama, maybe Locke Ober for martinis and lunch? I don't much like No. 9 (overrated, IMHO). Perhaps a small plates kind of place, so we can have a leisurely multi-course-fest/feast? Food is #1, setting #2, price not so much an issue (it is lunch after all).
Maybe Bristol Lounge or Grotto or Pierrot Bistro? I've not been to any of these. The menus at Davio's and Ivy look interesting, but are they any good? Via Matta has been my go-to place for upscale lunches, so that's a pass this time. I'm drawing a blank on lunch options in the North End, besides Neptune which has been my other go-to place. (Who's on an Italian kick?)