This is madness, I tell you. Madness. The island pictures all look like the setting for a horor movie in which a dozen horny teenagers vacation on one of their parents' private island, and one by one they're (a) blown out to sea by a terrible storm or (2) murdered by an anonymous blogger.
 

And, you have trouble with this?

Had I won that lotto, the island would have been one of MY first purchases.
 

Ha ha! That's rather a disincentive for Bean to accumulate wealth, isn't it?

Gloomy island with ruins? I'm not big on gloom, but I am big on ruins. To tell the truth, I've dreamt of castle ownership as well. Some good castle islands have appeared in Scotland and Ireland.

Sunny tropical island? Now you're talking. I much prefer warmth to the cold. I can definitely see myself on a tropical island paradise with boat, scuba gear, blender, and margarita mix.

There is a third alternative. Greece and Italy have offered islands with ruins. While not exactly tropical, I figure they're warm enough, and hey - something from the Greek or Roman Empire to admire.

That's the great thing - there are so many options to consider. Big or small? Developed or no? Remote or close to civilization? My wife or Bean's?
 

Oh, crud! This is how I find out that my wife is running off to a set of Gilligan's Island to catch cholera with one of my best friends.

Oh, well. I guess it's time to start drinking and gambling.

Thanks, little buddy!