Wish I had the time off from work. I would do it. I would rather go south though. Weather is always a factor. I would rather end my trip in a place as beautiful as the Keys. Ending there would be a greater reward in my opinion. I am a diver also and love clear blue water. To be fair, I have not sailed in water North of the Outer banks. I want to sail the Chesapeake. Life is short. Do it, I say. Any thing you do is a risk. Good common sense, pre-planning and good equipment should reduce the risk. The reward is greater accomplishing it in a small boat, like the C22, in my opinion. Please share photos, video and trip info. Would love to hear about your trip. I would take more spares, Outboard, rigging, etc.. So much to see, I would want to have a lot of time, so I would have more time on the hook and daylight to see stuff. I would definitely plan stops and determine how many miles to sail a day with several days allocated for bad weather. I should start planning my trip South now. I wanna go so bad. I think I would have a distant destination and a closer one. I would rather cut it short to see more stuff than to pass everything and miss it.