Small dinghy may need some effort to sail, but nowadays large sailboat can be operated single hand, need more than one person just for shift. And with the satellite weather forecast, it's very safe.

Even you never tried before, just join a small sailing club, take a lesson, only cost like a few hundreds. Those small clubs usually they have some boats up to 25 feet, but you get the whole idea of sailing. If you are really interested, you can take some other courses in u.s. for bigger boat and some advanced skills. Those are not cheap, but still affordable, like a few thousands.

Later you can buy your own boat, insurance is not cheap though. Most of people never cross the ocean, just go along the coast, you still can go lots of places like that way, like Caribbeans : ) And you don't need a high end boat like shannon to cross the ocean, can also save a lot.