Narrowing it down

My nephew Bobby reports that his girlfriend likes an '80s band sounding "much like the Dresden Dolls" whose name begins with an S, or if it doesn't begin with an S it has an S somewhere in it. We determined that it was not Supertramp.

19th-century all-wooden whalers seem remarkably cramped from the inside, having to pack in whole bunches of bunks for seamen, not to mention storage space for whale blubber. (Note to self: be sure to contrast smallness of living quarters with vastness of oceans. Speculate on whales' concept of "living quarters.")

Road to Old Mystic Seaport goes through New London, taking us past the Williams School, which is where Cassie Ventura went to high school.