I think KOlive is spot on, if you don't feel comfortable hire help, however if you prepare, learn and practice you could do it. Put time on your boat as much as possible. I bought my first boat, 6 years ago, a 58', yes my first ever boat. For the next two weeks I did nothing but 2 hour trips from lake union to lake Washington probably 12 trips, and when on dock, I researched and studied. I also believed the biggest deterrent was docking. I did not want to crash my boat and look like a moron. I was scared of docking. But felt I understood enough of the rest to get going. I docked likely 200 times when not on those short Trips, just touch and goes, Port and starboard, tried it in close quarters (less than 20' between now and aft boats.), practiced every time the wind came up 5 more knots than my last practice time. After 3 weeks of these I felt very confident and could literally dock on a dime with winds less than 20knts. Next up was the rest. I hired a captain, which was a requirement of my insurance, planned on 4-8 hours a week of instructions for a few months, because of my ability to control the boat, go through locks, it was easy to get him to sign off after a few hours on the first date. We practiced MOB exercises, anchoring, emergency plans, went over key rules of navigation, all of this was learned via my research and learning from every resource I could. 3 weeks later, loaded the family and crossed the straight of Juan de Fuca on our way to Victoria. Then 2 weeks all over San juans. The key to that was realizing, the difference from me and another person who I greatly respected and spent many many years boating out of Newport Oregon on a 32ft boat, was I'm not a panic person: I think that is key to being a good captain. If you get overly stressed during your test outings, if you get tunnel vision when times are tough, please recognize that and seek profession help for the trip, until you are confident and comfortable. Everyone will be looking to you for the answers. You need to have them. My wife always questions me, when we get challenged and I enjoy it, why do I enjoy it, because next time I will have that experience under my belt, if I was a panic type person. I would think of that 40knot docking experience as something I nEver want to see again, I treat it as hey, I got this, done it before. You must know your equipment, you face a much more difficult challenge than my first. If trip. Crossing the bar. If you pick a good weather window, your ocean crossing won't be that bad, but the Columbia bar, fog, and being able to handle trouble like hitting a log and what to do, is the real challenges. If you don't have knowledge through research and testing your self. If you are a panic person ( which can be overcome through controlled experience). If you don't know your boat instruments, or dont know how to use the equipment under distressed. Then don't go....but if you spend as much time as you can, practicing, testing yourself, learning from others, books, websites, groups like this and most importantly, if your confident and comfortable, go for it!