You could, but the boat probably would not be balanced properly, since it will want to head downwind... If you fall off, that would be bad.
IMHO, it might be better to sail with just the main sail, since that will tend to turn the boat into the wind, rather than have the boat run off. If you should fall in, the boat will be easier to get to if it is just sitting there in irons, rather than if you have to chase it.

__________________
Sailingdog
Telstar 28
New England
You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Captain Malcolm Reynolds, Serenity (slightly edited)
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