1. Who? - We would need 7 players and an adjudicator. I'd prefer if everyone was from the webdiplomacy forum community, or has at least been around for a while.*
2. Where? - I have a personal preference for Chicago, as it is quite a central location, especially if people come from Illinois, Wisconsin, Indiana and Michigan. I have access to some conference rooms to play during the daytime, that would serve as excellent locations for a game of Diplomacy.
3. When? - A weekend between now and the end of August!
4. How? - Keeping with the traditional conception of Diplomacy being very much a 'gentleman's game', I propose Western Business Attire or other formal dress code, and plenty of tea (or wine, depending on the time of the day).
Basically, the program would involve people driving/taking the train to Chicago (or other venue), getting lunch and playing from then on, for as long as we see fit, before taking off and going back to being boring usernames on this website.
* krellin is not invited, even though he claims to be from Michigan.