DSK wrote:

Which side do you back the main to sail off on a port
tack?


It depends. What is the keel configuration? Where is the
mast stepped fore/aft? Relatively few boats will fall off to
the same side the sail is backed, but some definitely will.

I'm glad you brought that up. Some boats need the main
backed on the opposite side. The Ensign--a full keel design,
as I recall, needs the main backed on the same side, ie
backed to port to fall off to a port tack.

BTW, this is one boat that where I've tried to sail backwards and
failed. I tried backing the main on either side in succession to
try to keep the boat centered on the eye of the wind and found
that if it starts to fall off, it keeps going. Note I had the jib
furled
to see if that would help and had no luck with that either. The
attached rudder is not a big help and is probably the single
biggest factor preventing this activity.

Being a full keel boat, it doesn't heave-to like a fin keeler. While
a fin keeler can keep the main sheeted in while hove to, the
Ensign needs the main eased.