Singlehanding is technically a violation of the COLREGS, since a sleeping singlehander can not keep watch. Most singlehanders will nap for short periods of time at night and sleep during the day, when the other vessels are more likely to be alert and keeping a good watch.
If you are at sea, you can't really drop an anchor... it is usually to deep.
There are no lights that are specified for a singlehanded sailor getting sleep.
Even if you deployed a sea anchor, you are technically UNDERWAY, regardless of your boat speed over ground.
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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.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.