The trip you propose is not a mai tais in the sunset deal. It is a longish coastal
passage, and the
weather is very changeable this time of year. Look at the
weather and
wind maps, there are strong winds to deal with. The waves accompanying them will find any
leaks your boat may have, and the motion may make both you and Chesty sick. Such conditions are extremely tiring.
Fatigue is the single-handed sailor's worst enemy. So do your homework, and if you are not already an experienced sailor, you really need to spend some time at sea before you leave so that you can
work out whether or not you or the dog get seasick, and how you'll function when shaky from throwing up. Some people throw up, and then feel fine, others, it's more like the flu and they get worse and worse, can't take in fluids, risk dying from dehydration. It's only a worry when you can't keep
water down. Can happen with the dog, too.
I would hope you would take crew, especially if you lack ocean experience.
How good idea this is mainly depends on your prior experience.
Ann