Odd responses, single handing sailing is not illegal. and can be insured.
I have chartered or rented a small sailing vessel from a charter company and gone sailing by myself.
Locally,
boats were small
Cal 20 or
Catalina 22 I took them out for the day and went sailing by myself. With the full knowledge of the chartered company. Nothing hidden.
I never asked them to charter a 30 ft boat by myself, I did move a couple for them. By myself. I was an instructor for their
sailing school. They expected me to be able to sail one of their
school boats by myself.
I routinely chartered 30 to 35 foot boats with just my girlfriend and myself. She was not experienced, I might as well been single handed.
Going to sleep and not keeping a look out is illegal. Nobody actually cares but would probably be a show stopper for a charter company.
Chartering a
small boat with the intention of doing short day
sails is not illegal. Convincing the charter company you have the ability to do so might be more difficult.
The boats won’t be specifically set up to single hand.
So call around, ask about chartering a
small boat. In an area you can sail from A to B within a day’s sailing.