My vote is for Newport, RI for the "Sailing Capital of the......" No particular reason, but I think it has more of a sailing history. DRB
Now thats so untrue. United States was first colonized through the Chesapeake, Jamestown etc with British ships looking for deep water ports. Annapolis and Baltimore were among first on the list as ports. Annapolis has been one of the 5 capitals of the United States. Annapolis ignomy of being the largest slave port where slaves were brough from Africa and landed first in Annapolis. Alex Haley famour book ROOTS s written about Kunte Kinte who landed in Annapolis ans was sold in its slave house on Ego Alley. Annapolis played an important part of the War of 1812 as a garrison for the British fleet.
I admit, I'm partial to voting for Newport. I've been coming to Narragansett Bay for 25 years and know I still haven't seen it all. Within a few hours sail, there are multiple islands and even more destinations on the Bay, if you aren't up to a coastal passage. You can head down Long Island Sound or up Buzzards Bay and spend a lifetime trying to get to all the ports. You can have anything from a 5 star experience to a quiet anchorage and everything in between. And summer sailing conditions are usually ideal, absent the threat of hurricane.
While I love the Annapolis area, it seems all admit that the summer is hot, humid and has light wind.Minniewaska
Everything you said is true about the Newport area could also be said of the Annapolis and Chesapeake . The many places to anchor here are unbeleiveable, harbors where you can actually anchor not choked by paid mooring fields. Rivers you can go up and anchor at every turn on the Eastern Shore with towns from the 1600;s. Anchorages in the midst of pure wildife not seen up north until you get to Maine/ While it is true it is unsually hot and humid here for two months ( thats why we come north to the LI Sound in August), our sailing season starts in March and ends near Christmas. You guys are have already put your boats away and we have a couple months to go here. So therre is 3 more months of sailing here. Many of us also do not put our boats on land in winter also. The think about the Chesapeak is you dont have to "look" or wait for an inlet or harbor to find anchorages...they abound everywhere. You also dont have to worry usually about rocks like the " Little Mermaid" holing your boat. On the Chessie current directuion or speed is never an issue and we look to sail for a weekend, all we care about is wind direction/ Up north current is king. We also find it cheaper to sail in the Chesapeake than up north.
We enjoy the best of both sailing worlds, and sail in both sailing worlds. We always encourage our friends to come north wirth us because we enjoy it. We also have met a lot of nice sailnetters on our travels north who have been very gracious, and have encouraged them to come south in the fall when the sailing here cannot be beat.
I think its a tie for Sailing Capital of the United States between Annapolis and Newport, they both have their charm and their advantages,,,some of which are the same. But the tie is for second place because I thing the NZ have it over both cities.