In your initial post you said there are not many sailboats out in your region of the bay. I've found this to be the case throughout the year in Virginia waters. I'm not sure why, but even at some of the best sailing locations the Chesapeake has to offer, sailboats seem to be rarely away from the docks, even on weekends. A couple years ago I was swatting the black-flies near the mouth of the Rappahannock River late one afternoon when a thundershower loomed over the western horizon. I opted to duck into Mill Creek and try to find someplace to anchor until the storm passed. This was in the middle of July on Friday afternoon.
Now, the last time I had been here was when Howard Kruse still owned Kruse's Wharf and a small fishing tackle store was at the end of the dock. My how things had changed. Every square inch of shoreline had some sort of pier attached, and the entire creek was a massive marina complex. Most of the boats were sailboats, which contrasted significantly from what was there two decades earlier. Some sailboats were absolutely huge, and most measured greater than 30 feet. Ironically, every one of them was tied firmly to the dock, only a few individuals were even on their boats, and from what I was able to determine by talking with them, most people just didn't leave the dock at all.
While searching for a spot to anchor, we encountered a boat hook floating in the creek. My sailing buddy fished it out with our boat hook, and an attractive, young lady on one of the nearby docks yelled and thanked us for retrieving her boat hook. We motored over and handed her the boat hook.(Hard to turn down a deeply tanned gal wearing a string bikini and a big smile.) I asked if there was someplace in the creek where we could anchor and she replied, no, but you can tie up here for the night if you wish, and pointed to an adjacent slip.
We spent the night and half the next day waiting for the weather to clear, then slowly motored out of the creek and back into the river. There was a gentle breeze from the southwest, so we raised the sails and sailed down to Cape Charles, which took about 10 hours. The night was spent anchored behind the concrete Liberty Ships at Kiptopeke State Park, which is a great anchorage when the wind is howling from any westerly or easterly direction. During the entire trip south, from Point Lookout, Maryland south to the bay's mouth, we only saw a handful of sailboats, and only two of them had their sails up. The others were motoring along the main shipping channel.
On our return trip north, we sailed through Tangier Sound, exited via Kedges Straits, then sailed to Solomons, again seeing only a handful of sailboats in more than 120 miles. Now, Solomons is loaded with beautiful sailboats, many of which were large multi-hull models that were extremely well appointed. During the next two days, which was a weekend, none of them left the dock. During the night we anchored in Saint John Creek along with about a dozen other sailboats. When we left the following day, most of those boats were still anchored.
The trip from Solomons to Annapolis went pretty quick with a 12 to 15-knot southwesterly wind sending us flying up the bay. Despite excellent sailing conditions, and passing through the bay's sailboat capital, the only sailboats we saw was a small cluster that appeared to be racing near the Severn River's mouth. The next batch of sailors was not encountered until we reached Havre de Grace.
Sorry to be so windy about this, but I found it puzzling that the highly touted waters of Chesapeake Bay. with it's massive fleets of sail and power boats, is often nearly devoid of boats--even during mid summer. Granted, weekends, particularly when the weather is ideal, certain areas can become somewhat crowded. But, most of the time, the Chesapeake provides a wide expanse of sailing opportunities that is hampered only by crab pots.