For me, the bigger boat in retirement is to make it more "livable". My Hunter 280 was fun to day-sail, was pretty easy to single-hand, but really lacked a useable cabin (didn't even have a fridge to keep the beer cold)....A lot of talk about bigger being safer and more comfortable. But is it more fun? What about the old image of the retired guy in a flat hat, driving the sports car we mistakenly associate with youth.
Which is more fun to drive, a Winabeago or a bicycle? The answer is a bicycle. If you find it undignified, the weakness there is obvious, and for most of use it is only physically difficult because we don't.
So the question is which is more fun; a day sailing boat or a cruising boat that we don't cruise (and very few "Cruising boats even leave the dock, let alone cruise more than 2 nights a year)? I've had fast boats. I've cruised more than most and less than others, but about enough (I'm a little boarded with that). I'm ready for that sports car. Maybe a lot of us are, but we're just afraid someone will see that as a step downwards in social position. I don't see it that way. Again, the Alerion 28 makes my point, although that is not the boat for me. The point is that it is a fine boat for the person who doesn't feel like sailing a house.
My O'Day 322 is still very easy to single-hand, but is more stable, and has a much more usable cabin. After spending a night recently in the 80-degree cabin, the retirement boat will have A/C for sure.
To cover the "wild ride" youth toy, I bought this BMW Z3 M Roadster! Great fun getting to and from the marina!
Greg