Captains, thanks for the input and helpful tips.
Here are my answers chronologically as posted.
1. I think my Jeanneau 37 has 50'2" mast height, so I have a few feet to spare. I hope it should be OK.
2. Pass the north side is noted.
3. The trip objective is to chalk up experience with a minimal preparation. Trying to learn how to handle the unexpected in a relatively safe coastal water near home. I have less than two years to get ready to sail solo in the Pond and beyond. My son (22) may join me, but I can't count on it.
4. I have not worked out the details in passing through Cold Spring. I will play by my own instinct with Plan B in the back of my head.
5. Hahha, I have read you blog many moons ago. Good read
6. I try to get to Cape May as soon a possible. If we have time, we will take a slower pace in Cape may. We have fond memory from the past visit. It is too bad that there is no water taxi in Cape may and we have no dingy to shore. So we need to find an inexpensive way to dock my boat for a few hour or overnite.
7. We will be departing Annapolis landing Marina at 8 pm today (wed, 28th) for Chesapeake City. It is about 50 nm, so 10 to 12 hrs trip as planned. Your Aston Martin 40 is much faster than my "rental" Yugo 37,
8. I figure that if I can get to CC by 8 am, take it easy for a couple hr and check out all system before heading out the Delaware Bay. The high tide peaks at 10:05 am on Thursday at Delaware City.
Winds are currently N'ly but when the cold front hanging over our head passes it will switch to S or SW'ly. Don't get too engaged with the marine forecast. Frontal passages create local effects and forecasting just when it will pass a particular point is more art than science. From our perspective it will happen when it happens, sometime late Wednesday or early Thursday
Good to know
Hopefully the S and SW wind will stay our return trip back to C&D canal.
10. We have sailed in the Canal in the past, it is our "backyard"....
. But we used a much smaller boat (Catalina 14.2)
11. No intention to go against the current in Delaware river this time. May be next time.