As for parking during Regatta, if you are getting to the Yacht Club early in the morning, finding a spot is not that difficult. After 10 or 11 a.m. and later is a different story.
As for motoring a sailboat to Oyster Pond...
to be honest, I haven't spent much time in Oyster Pond.
Last time I moved a sailboat from Simpson Bay to Oyster Pond
was two or 3 years ago. I think it may be a bit over an hour, but don't really remember, for when I did it I was under no time restraints and was not in any hurry (even did a little side tour into Great Bay for passengers).
You're not staying on the boat! Wimps! <img src="http://www.traveltalkonline.com/forums/images/graemlins/Grin.gif" alt="" /> <img src="http://www.traveltalkonline.com/forums/images/graemlins/Wink.gif" alt="" /> <img src="http://www.traveltalkonline.com/forums/images/graemlins/Grin.gif" alt="" />
.
