Annapolis & Vicinity
 The very things that make Annapolis the principal yachting center on the Chesapeake Bay are the same things that make this the least attractive part of the bay to me.  It's not that this is not a great sailing and cruising area, it's just that there are too many G_d D__n boats. 
I started sailing in the Annapolis area in the early 1970s, and at that time I was used to the water way congestion that existed between the Bay Bridge and the West River.  I hadn't sailed in any other conditions.  I left this area for a few years in the mid 1970s to work on a DOD contract in the Panama Canal Zone.  When I returned in 1976 I moved my HR25 sailboat to Solomons, MD in anticipation of buying a new sailboat, which turned out to be the Columbia 8.7 I named Vela Llena.  I have returned only infrequently to this area over the intervening years.  Normally the Choptank River is the northern limit of my weekend cruising territory.
Every time I sail to the Annapolis area I end up wishing I had selected a different destination.  Since the bay offers almost limitless alternatives there is no reason for me to suffer these congested waterways and crowded anchorages.  Of course this is just my prejudice, others regards this area as a prime destination.
Annapolis is certainly the sailing center of the Chesapeake Bay if not the entire East Coast (I'm sure Newport, and more than one city on Long Island Sound would argue with the later assertion).  I took my first formal sailing lessons at the Annapolis Sailing School in Eastport in 1971.  I first learned to appreciate Bouillabaisse at the Dockside Restaurant and the Charley Bird Trio at the King of France Tavern about the same time.  When I purchased my first sailboat in 1972 I kept it on the South River, about 10 miles from the Annapolis water front.  I may not qualify as one of the old guard of this city, but I certainly have more history with it than most of the people you might encounter around the waterfront today. 
Here are a few old pictures of the Annapolis water front from the early to mid 1970s.  These pictures were taken on 35mm slides and have been stored in slide trays for more than 25 years.  I just now (2002) scanned them into JPEG files.  Looks like I was few years too late to preserve the quality of the original slides, but I think they will still be of interest to people familiar with Annapolis today and how it has changed in that quarter of century.
Click on picture to view at full resolutionSpa Creek looking toward what I believe is the old Trumpy yard.  Trumpy had been out of business for a year or more, but the yard had not been converted to the multiple marine business complex that it is today
Click on picture to view at full resolutionOn this late January day the temperature was in the 70's and many boats were out for a day sail.  Funny, we didn't call it Global Warming back then.  I think we called it a nice day.
Click on picture to view at full resolutionHere the Cal 25 fleet is beating up Spa Creek toward the finish off the Annapolis Yacht Club.
Click on picture to view at full resolutionMore Cal 25's in action.
Click on picture to view at full resolutionA 24' Rainbow on the way out Spa Creek for a day of racing in January.
Click on picture to view at full resolutionView from the Spa Creek Bridge looking toward the Naval Academy grounds.
Click on picture to view at full resolutionThe Annapolis inner harbor before the oyster boats were kicked out and it became known as Ego Alley.
Click on picture to view at full resolutionLorea's Tavern was the local waterman's bar in the inner harbor.  Creaky wooden floors and 15-cent Rolling Rock beers at the bar produced a marked contrast the upscale restaurants and bars that have occupied this space since the watermen left and the tavern closed.
Click on picture to view at full resolutionLooking toward the circle from the inner harbor.
Click on picture to view at full resolutionTypical summer scene on Spa Creek as seen from the bridge.
Click on picture to view at full resolutionThe docks on Spa Creek directly opposite the Annapolis Yacht Club.  There were a lot more wooden boats in the Annapolis marinas than you will see today.
Click on picture to view at full resolutionAn elegant wooden motor yacht in Spa Creek, off the Annapolis inner harbor.
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Another wooden yacht, this time a yawl, anchored off the Annapolis inner harbor.

Click on picture to view at full resolutionI believe this was second or third Annapolis Boat Show.  It was called the In the Water Show because at the time it was one of the few shows, if not the only show,  where the boats were displayed in the water and not inside a convention center.