New England bound

I currently live in NH and have lived in MA or NH my whole life (w/exception of Colorado for a year); went to school in Boston, work north of the city now.

If you're looking coastal and in NH then you're kind of limited because there isn't much actual coast in NH, but Portsmouth is a really good choice. It's a great city for walking around in the summer with tons of really good bars and restaurants and lots of live events throughout the summer. Matters who you talk to but it's not cheap to live there. Taxes will be high; in NH no income tax but high property taxes. If you want to be close to Portsmouth but not IN the city then Rye is probably the other option I'd suggest in that area. Generally the closer you get to the coast there's only one way in and one way out of the cities as they've done a lot to preserve the lands around and not build roads everywhere so you just have to be prepared in the summer with beach traffic.

Lake wise if you want to sail you definitely have to go north. Winni is a great area, very congested during the summer with a much more laid back feel in the winter without as many people around. It'd be expensive to live right there, I actually don't know anyone that lives up there as most people just go up on vacation or own a 2nd home there.

If the sailing could take a back seat and you just want general nice places to live in the area. I live in Hampstead NH and love it. Londonderry and Windham NH are really nice and close to the highway (I93). In MA you already mentioned Newburyport, going west you have Boxford, Groveland then a bit more west is Andover. I93 runs north/south and if you're north of the city and east of 93 you're at MOST 30-45 minutes from the ocean, further east less time to salt water obviously.

Any specific questions on towns or areas let me know.