Re: The #1 sailing city in america
It really so much depends on what someone wants from sailing doesn't it?
For instance, if someone wants to learn to handle just about anything Neptune can dish out, then hands down, the SF Bay area. It is probably the most challenging place in the US to sail. But it's a crowded and expensive place to live and Cal has a lots of environmental laws that are very tough on the pleasure craft industry.
If on the other hand you want a beautiful area with lots of islands in fairly sheltered water, then the PNW can't be beat. That is if you can put up with 300+ days of rain a year, cool temperatures most of the time and rocky anchorages. (somehow, rocks seem harder than coral; I know it's not true, but it just seems that way).
LA/San Diego are very limited in what sailing you have and I've never found either area to be particularly attractive. Only a few, very crowded anchorages on offshore islands, and I don't know of anyone who, say, leaves Marina del Rey and sails up the coast to, say, Malibu, anchors the boat and goes ashore by dinghy for a drink at a beach side bar.
The gulf coast is an incredible area, but extremely hot, humid and buggy in the summers. The west coast of Fla is also pretty buggy and quite dangerous in the summer t-storms that roll through each day. The Gulf of Mexico is not what most sailors would call a favored destination.
The Keys, though incredibly beautiful are not a great place for sailing; pretty shallow, a lot of low bridges, extremely regulated and not the most hospitable place in the US, especially in the winter.
The east coast of Fla, up through Ga, would be a great liveaboard/working place to live, but coastal sailing there isn't much better than SoCal, except you have the Bahamas a short hop away for vacations.
Charleston, SC has a wonderful harbor, is a wonderful city and there are a few destinations within hours that are enjoyable respites. But the summers are brutal; very hot and humid, with t-storms nearly every afternoon.
I've never seen the lure of the Chesapeake. There are some great places to visit like Alexandria, Annapolis and my favorite, Solomon's, but I find the sailing and scenery to be very mild and boring, the water unattractive and uninviting.
NYC and Long Island Sound were a complete disappointment to me. Every time I found what looked like a perfect anchorage on the chart, I found a mess of moorings that were taken by local boats, so even if I'd wanted to visit, there was no room. Mystic was cool, but oh so touristy, that it wouldn't be a place I'd want to live. The one bright spot in the whole area was Stonington, Ct, where they even had a designated anchorage area for visiting yachts.
I loved the Newport/Narragansett Bay area and though I did not get much of a chance to sail the area, it seemed to be a very good sailing area. The islands off shore and the many bays and harbors from Newport to Boston could keep one occupied for many years, I would imagine. I did find inexpensive dockage ($500.00 a month, utilities included for a 50+' boat) in the area and though most people do haul their boats for the winter, I found living aboard to be quite a lot of fun, if chilly.
I have no experience in sailing the waters of New England north of Boston, though intriguing, the winters are probably as brutal as the summers in Charleston, leaving one with a pretty short sailing season.
But if I had to choose one area to sail in for the rest of my life, it would have to be the SF Bay area. With the rivers inland and the few places to sail to up the coast, I've not found a better place for variety, reasonably comfortable year around weather and just plain fun sailing, in the US. But I'd probably have to win the lottery to afford to live there again.
"Any idiot can make a boat go; it takes a sailor to stop one." Spike Africa aboard the schooner Wanderer in Sausalito, Ca. 1964.