I'd do it myself. I wouldn't take anyone along.
It's like any new toy, I want to sit down pull the wrapping off myself, quietly read the instructions and put it together... All by myself.
I feel I learn more, learn at my own pace, and don't feel like a dork in front of someone else.
Then off I'd putter on the motor, till I get too excited and have to start playing with the sails etc.
I'd probably have intentions to make them short days... But prolly wouldn't anchor till near dark.
Also prolly make a few mistakes, but I'm alone on my boat and I'll make whatever mistakes i want
So my advice is to go play with your own new toy yourself. You will learn more and have much much more fun!
PS If you sink it's only a river, you can swim ashore.
PPS in case you don't sink take a bottle of wine or a few beers to have one night along the way!