Wow... What a debate!
It is true that sailing in the NE is "pretty", but rather unforgiving when you make "slight" navigational errors. Even the smallest of errors results in an audible CRUNCH, CRASH, or other Batman-like sound effect echoing through your hull. If you're lucky, you only scratch the jelcoat or crack something. Quite often your "little mistake" results in a Damage Control Final Exam in very chilly water where you do your best to plug, patch and cover whatever hull damage you've managed to cause your Second Home. Even Coast Guard cutters have been known to find previously uncharted rocks and pay dearly for their mistakes (USCGC SNOHOMISH, uncharted rock, Jan, 84)
On the Chesapeake Bay, you don't often find things on the bottom that go crunch in the night. At worst, you find a well-known, well-documented, near-vertical sandbar that results in embarrassment and time spent in reflection upon your recent misfortune. You may even compound this "injury" if witnesses are present. Some spots can be as entertaining as an early-Spring Saturday morning at the boat ramp where people launch vehicles (with their boats) and forget to install drain-plugs.
The Chesapeake Bay and her tributaries have more shoreline than the entire East Coast.
Lots of places to explore and spend a weekend.
No one mentioned another "Sailing Town" that makes a claim to the Title: Kemah, Texas.
If you are looking for the place with the most boats per capita, then I doubt there is another place that can beat Kemah. When I lived near there, the year-round (permanent household) population of the town was right around 1,000. There were more than 1,000 sailboats in the marinas in and around Kemah. If you have trouble believing me, please find it on Google Earth. I didn't believe it when I first heard the claim, either. When I lived a couple miles from Kemah, I kept my boat on the trailer. I couldn't afford to keep it in the water. Of course, I lived there before the last hurricane blasted through the Texas Gulf Coast, so I'm pretty sure quite a few of Kemah's floating residents are no longer considered in the 10-year Census...