Not enough wind shifts to matter for planning purposes.
I always check the wind direction when I leave the dock
and also the prediction for the wind direction later in the
day. I want to know if the wind will veer, back, or hold
steady during the period I plan to sail. It is rare to see
a windshift that wasn't either predicted, or expected. There
are effects that happen at certain times of the year and
certain times of the day. Like the late after noon lull on
my side of LIS in the hot days of summer.

Given a choice I like to do what you do, go across the
wind on a beam reach. It happens less often than I'd like.
Mostly we have Southwesterlies. Now if we had a good
Westerly I could blast across to Port Jefferson and set a
record doing it. We rarely have easterlies so that means
heading east is easy, coming back west is 50% longer. If
we do have an Easterly or Nor'easter, they can be very
rough, but not nearly as bad sailing West as sailing East.
These have the added benefit of not lasting long so the
return trip is often downwind too after the wind clocks
around.

For these reasons on short trips I head south. Medium trips
I'm more likely to go west into the wind, and long trips I head
east and recognize that getting back might be a problem or
take an extra day to get back. If there is an Easterly I would
head west or stay home.

"Scotty" wrote
never have wind shifts up there, eh?

"Bart Senior" .@. wrote
I prefer to go upwind so I can more precisely control
when I get back.

"Joe" wrote
When you sail and have the option...... do you work up
wind first so
you can have a fun rocket ride home, or do you have a
blast hauling ass
downwind then work your way home?