More Bay Memories
I was on the Chesapeake for 7 years and really miss the wonderful anchorages and great towns, as well as the sailing. I would take a yearly pilgrimage from Deltaville, where I kept my Vision 32, to the upper bay. It was easy cruising in some really wonderful places, at least most of the time.My first year on the Chesapeake, I had a San Juan 24. It was a great boat that sailed well. However, Jon Dawson's advice is well founded. When the wind and waves pipe up, its tough to get anywhere upwind, most especially in a small boat, and the outboard will be out of the water most of the time, rendering it useless. However, if you aren't in a hurry and can pick your days, you could have a wonderful sail.To Bob's question about travel time on the bay, this is how I used to go about a sailing trip. I kept my boat in Deltaville on the lower bay, and my destination for a weeks vacation was normally the upper bay, Annapolis, Baltimore harbor, St. Michaels, ect. It was about 100 miles, so I would leave at dawn and do 50 miles a day. If my speed was under 5 knots, I would motor sail. That brought me to my vacation sailing area in two days, normally easy, if long, sailing with the help of an autopilot. It would also put me into port in the late afternoon, time to anchor, even dingy into town for dinner, and early to bed. Once you have reached your cruising grounds, short day-sails are all you need to get you to other great anchorages.The other alternative is a lot of short days with more stops along the way. Since my destination was further north, I chose the former plan.I hope this helps.