What time of year are you interested in? (FL in the summmer? Maine in the winter?)

And what kind of budget are you looking at?

I'm sorry, I didn't realize that I did not put a time of year. We are considering mid June or September.

Budget: I am slightly flexible. I would be shooting for no more than $200 per night but if a really great place caught my eye I could pay a little more.

Seaside
St. Augustine

Small, out-of-the-way, charming town: Inverness, California. Great hiking/walking. Nor Cal woodsiness. Very cool bodies of water. About 2 hours north of SFO.

For North Carolina I would try Okracoke: http://www.bedandbreakfast.com/ocracoke-north-carolina.html
I've camped and eaten on Okracoke Island but never stayed in a B & B. Warmer than Maine but cooler than GA or FL.

Sanibel, Captiva, island living at it's best, it is warm but nice breezes. Lots of great food, pedestrian and bicycle friendly. The gulf is warm and not as rough as the Atlantic, never been to the Pacific.

While you didn't mention Mass, Plum Island sounds like it mihgt be your cup of tea. Its a barrier island near Newburyport - long beach to walk on, quaint town, food is good but there's not a huge restaurant scene.

Goose Rocks Beach in Kennebunkport is another location that might work.

Beaufort, SC

I agree with MJT! Beaufort is a great little town.

In September: Pick any Cape Cod town. Chatham is great. Kreme and Kone for fried seafood anything and great burgers.

Fernandina Beach on Amelia Island (FL)
St. Augustine
Charleston - Larger city with beaches nearby
Outer Banks, NC (never been due to driving distance but would love to go)

Sannibel or St. Augustine. In St. Augustine stay at the Casablanca Inn. It's great!!
http://www.casablancainn.com/

You guys would love Rehoboth Beach or Bethany Beach in Delaware !! Our favorite places !! We have a beach house in Ocean City Maryland and that is nice too but no way near as quaint - we like to drive up to Bethany and Rehoboth for the day - YOU WILL LOVE IT !!

We've been to the Outer Banks, NC, many many times and love it but I wouldn't say it's quaint. There's the beach road which is lined with beachy businesses and then the highway which is lined with small strip malls, supermarkets, restaurants, etc. The beach is beautiful and there's an abundance of non-foodie types of restaurants, but it's not really a place where you can browse a quaint little town unless you go a bit inland, e.g. to Manteo.