I will echo Cam about the Chesapeake -- it's easy to sail right through November, especially with a cabin heater. So if you get here in late October, you can take a nice leisurely trip down the Bay to Norfolk. There WILL be more than a few days when it will be better to stay put, but by and large you'll have nice sailing. Expect some frost on deck in the early morning hours as November progresses, but it will melt fast.
Let us know if we can help in any way.
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT