I love Annapolis very much, but I wouldn't call it hip or even progressive...we're kind of the freakish ones when we go there (and DH felt that way when he lived in that area). Most people are pretty conservative/preppy...it is a higher income area, and everyone we know there (and we know a lot of people there, DH lived in the immediate area for many years and went to school there) is very mainstream (though still nice people!) and lean to the conservative side. There is a store that sells natural health related books and supplies, an indie health food store, and there's a birth center in the area, but that's not enough for me to think of it as an especially progressive, NFL-friendly area.
Despite this, I think Annapolis is a beautiful area and DH is applying for jobs that will hopefully allow us to live there in the very near future (we're in NoVA at the moment). The DC area in general does have a good selection of alternative medicine practitioners (including non-vax friendly), and there's tons to do here. Maryland overall has a large homeschooling population, and we've never had problems finding activities for homeschoolers (this was when my sister and myself homeschooled), and there is a large selection of homeschooling groups to join.
DC is consistently in the top few veggie-friendly places in the country. There are LOTS of ethnic restaurants that are veg friendly around here, and several veg-specific restaurants (Java Green in DC is my favorite, it is delicious!) and smaller health food stores (My Organic Market, Roots, David's, etc., plus alt medicine stores like Smile Herb Shop -- love this place!). There is also a Green Festival in DC, and the Prayer Vigil for the Earth in October (a pro-peace event inclusive of many different belief systems -- we went two years ago and it was really cool)...
We've looked at places to live at the beach, but so far there's no work in DH's field available there.
I would absolutely love to live at the beach if he could find work there, but nothing has turned up for him so far. Annapolis is my #2 choice.
Obviously I'm quite a fan of Maryland!
DH and I left about five years ago for college and moved around several times in three different states, and we keep ending up back here. We've decided to embrace it this time, and we're home for good.