A limited $0.02 worth...
<snip> Lots of eating out. I'd love restaurant suggestions.
I saw my first whale in Maine leaving from Bar Harbor. It was July. Went on the same trip another year in June and didn't see a single whale. May will probably be too early to see them.
Yes, early May is definitely too early for a productive whale-watch trip. In fact, they likely won't yet even be running whale watch trips out of Provincetown at all in early May.
I am sometimes reluctant to make restaurant "recommendations", since personal tastes vary so widely and "one man's meat is another man's poison". Moreover, you're not going to Brewster until over a year from now and things can certainly change in a year. With all that disclaimer clearly stated, I'll mention two places...
Brewster Fish House on Main Street (a.k.a. Route 6A) in Brewster is excellent. Very small interior space, so the closely spaced tables create pretty tight quarters with your fellow diners. Perhaps just a bit pretentious and certainly not inexpensive, but not truly crazy prices either. Well prepared seafood and good service.
Considerably more informal and with a much longer "track record" is the well established
Land 'Ho in the abutting town of Orleans, near the center of town. Popular with locals year 'round. Not necessarily "rowdy", but usually busy and often a bit noisy --- the bar and the restaurant seating are only marginally separated from one another by a waist-high partition. Their kale soup with linguica (a mildly spiced Portugese sausage) is known and loved far and wide. Not an imaginative menu otherwise, but most everything on it is decent.
Having lived there, I think I've been to every restaurant in and around Brewster at one time or another (...there aren't really all that many, truth to tell), but that's all the input I can offer with any real confidence a full year-plus in advance of your intended future visit. Hope this still helps you at least a bit.
