I have a Catalina Capri 14.2. Although I have a Honda 2 HP outboard, I hardly take it with me. If the wind dies, I just sit until the wind picks up or some passing by to give me a tow.
Just bring your cell, portable VHF
and SPOT, just in case the unexpected. I have sailed this way for 10 to 15 years. It is totally doable and fun. I have oars, but I am too lazy to use them unless I am in the shipping channel.