We are taking legs of your trip this summer with 4 boats from the Patapsco (Baltimore) area of the Chesapeake to Mystic. As others have advised the beat down to Cape May will take 3 days on the outside route due to the prevailing onshore breeze. I have done it a few times and not single handed either. On our trip up we are doing Chesapeake to Cape May to Block Island on the outside, Comming back we are doing the LI Sound and anchoring in New Groton, Essex, Liberty Marina (by the Statue of Liberty) Manesquan, Atlantic City, Cape May and then up the Deleware.
The advice about the New Jersey inlets is spot on. The three I mentioned, Manesquan, Atlantic City, and Cape May are the only really good safe ones. The others are trecherous at best
The advantage of this route and then 40 miles day trips down the Chjesapeake to the ICW is that you will have places to anchor and explore even when you hit some tough weather days. October has usual weather systems pressing through every 2-3 dyas vs the summer. We have had some of our best NW wind runs for distance down the Chesapeake in October, and that time of year the scenery in the rivers here at leaf turning time and bird migration time is outstanding not to mention to power boaters for the most part have put away for the year. Enjoy the day sails on the Chesapeake as once you hit the ICW it will be a long motor boat ride. Feel free to PM me for anchorages or info on the Chesapeake
Last edited by chef2sail; 02-28-2008 at 09:36 PM.