Riding is real pleasant here, after September. Most of the coast over there pretty well sucks, but go inland a little ways, and it gets to be down right pleasant. Nothing like the PCH, Grande Escalante, or Beartooth, but nice roads. If you head up to around my place(NW of Orlando), you even get to ride roads with corners and real hills, and not on just freeway ramps. Lots of get togethers to go to in FL, especially in the non-summer months:
Aug 27th, RTE
Sept xx, another RTE
BikeTrailerfest Chili Feed and COG breakfast
Early November, Smackdown at the Shack, RTE at a kick a$$ Q joint NW of Jax,
Early December, probably another RTE
Saturday 'tween Christmas and New Year, The Last Blast BeforeEMid-late Jan, probably another RTE.
Pretty much all RTE functions are at one-off type places, lots of 'em don't even take plastique. Old Florida.
Examples:
http://www.wallowatthehollow.com/These folks do a bang up perfect job with a large group. Don't let the cruiser motiff scare ya, way cool place. This is the breakkie RTE on 27 August.
http://www.zggtr.org/index.php?topic=2429.0http://www.solomonscastle.com/boat.htmhttp://www.blackwaterinn.com/index.cfm?screenwidth=1024no web site, but:
http://local.yahoo.com/info-13879428-shack-by-the-track-ice-cream-st-george;_ylt=AkThIe69Zn1QO5L0V7xG4peKNcIF;_ylv=3?tab=reviews&allreviews=1#reviewsAlso MSTA puts on pretty much monthly RTE events, in both north and So FL.
November and December, except for the holidays, is also an excellent time to go bumming around in The Keys. Most years, we go camping for about 3-4 nights in early December, plan to this year. If you've never been, The Keys are an experience, no doubt.
So yeah, bring/get a bike.
Hope the family stuff goes well for ya, I'm dealing with similar with my Mum in MN.
Edit to add: Forgot about this little gem of a get together if you can get away for a few days, link:
http://www.zggtr.org/index.php?topic=1924.0