A Flying Scot is a great first boat for you and your family. They are beamy, roomy and quite stable for a CB boat of that size. That said, in all but light air, a Scot is more of an active rather than passive sailing experience. It's a great boat for you and your wife to sharpen your skills and enjoy some great daysailing adventures. You would have to try pretty hard to capsize a Scot -- not that you couldn't, but it would be pretty difficult. Go out in conditions suited to your abilities and the comfort of your passengers. You shouldn't put the boat on its ear when you're out -- it's a slow way to sail anyway -- but you should help your family understand that heeling is part of sailing. Remember that your wife and kids will get their cues from you -- if you appear anxious when the boat heels, they will be anxious. If you explain why you're heeling and that it's normal, they will learn to be relaxed. As far as reading the paper and enjoying a drink, a Scot may not be the ideal boat for that (except in light air), but I might suggest you get the admiral involved in sailing. Moving up to a larger boat will be easier once she's hooked and you have her support. The admiral on Grey Goose enjoys sailing in most conditions and we both still enjoy what she jokingly refers to as 'cocktail sailing' -- conditions where you won't spill your marguerita
. I say stick with and sail your Flying Scot for at least a year before considering a change.