I telephoned Gary Emich on 9 Apr 09. He's the go-to man for SF Bay swims: http://www.lanelinestoshorelines.com/
We discussed the possibility of organizing a swim in the Bay on 26 Sep 09, and how to deal with the complication of the DSE Escape from Alcatraz which is also on that day. He said that the tides will be very calm, so if we wanted to start our swim after the DSE folks start, that could probably work. (DSE swim starts at 8-8:15am, so we could probably start ~9am). He recommended aiming for Aquatic Park rather than the St. Francis yacht club because the weak tides would make swimming to the SFYC take a while.
I think a Bay swim makes sense for a JLL tribute, given all of the publicized swims Jack has done in this area. We could host a few practice swims and info sessions for folks who haven't done it before. For those who have done it before and want to do something a little different to increase the challenge: try going sans wet suit, or we could maybe arrange a ride/run to start after the swim. (I'm also considering the possibility of having a group of swimmers tow a small boat carrying someone representing JLL, but this might be too crazy.)
I promised to get back to Gary when I know more about how many people would be interested in doing it. Getting the permit is free, but hiring the support boat and kayakers could probably run ~$300-500 (though volunteers would help bring costs down).
The Dolphin club and South End Rowing club has their annual Escape from Alcatraz scheduled for our target "feat of strength" day, 26 Sep 2009:
As it features a swim from Alcatraz and a challenging run, it would be an excellent choice for a designated feat of strength, which Team LaLanne members could enter as a group.
The trouble is, only Dolphin or South End club members are permitted to do the swim. And you have to have been a club member for at least 6 months to qualify.
So unless they are willing to make an exception for our special group, this is probably not a viable option.