I learned by sailing with friends that owned boats, first out of San Francisco on a 40' a friend inherited for a few years on weekends. Mostly trips to San Diego and back, then a long trip from Ca. to Virginia when he transfered.
While in Virginia myself I crewed for friends a couple time to and from the Bahamas and Pueto Rico.
When we moved to Sicilly I got my own boat and logged many trips around the Med with friends as crew.
After almost 30 years I still consider my self an amature sailor, would love to get the experience to feel confident skippering a blue water trip but something like that will probably never happen, I'll probably always be Gilligan.
The cat is fast, ours has a tiny cabin, enough room for a head, bunk, and food prep/plotting table. Strictly a day sailor. The Hobie is about the same equipt wise just a few feet shorter, more stable on the water, and much slower.