Certainly your Hunter 33 can handle you plans. The more experiences you have On her the better you will be in terms of your ability. I would suggest you take some time on other comparable boats and also have some friends with more years experience sailing out on yours. That will help your learning
curve. There is not substitute for experience and usually you don't learn things my routine unless you have a certain amount of repetition. These are a function of time usually. That's what helps you learn how to handle the new and extraordinary conditions which get thrown out you. Sailing is fluid sport in a fluid medium. This will increase you confidence also
My suggestions about having others on your boat willl help expedite your improvement in sail trim, course plotting and even stjimple things like anchoring
. Certainly have enugh under your belt to venture forward to somle of the destinations you posted. Utilize CN with questions along the way as there are many on hear with large and differing amounts of experiences and knowledge.
After 40 years of sailing (since I was 16), a few trips acros the pond, some deliveries and sailing in the Carribean
, and 18 years of keelboat ownership
, I still learn everyday or get new ideas from fellow sailors.
Good luck with you new purchase