I did B2B as my first. Great race.
There's lots of chatter on here about GF, plenty to read.
If you look around much at all, I think this choice is pretty easy.

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@christopher_borden •
Spinning Spoke • Dimond Bikes • Flo Cycling • Castelli Cycling

I've done the Great Floridian 5 times and doing it again for a 6th time this year. Good challenging fun course. Much more difficult course than B2B, probably an hour slower course. This is the 25th anniversary race and should be a lot of fun!

I've done both, and while GF was my first full, I'd give the nod to B2B. Two big reasons. First, weather. GF will likely be warm and humid, whereas B2B will be cooler, but with the risk of being downright cold. I'd much rather be cold than hot, and I just hate the humidity. Second reason is participation. The GF bike course got pretty lonely, and I think there are fewer participants now than when I did it (2008).

Biggest downside for me of B2B is the swim: 2.4 mi is already a short swim (relative to the bike and run distances), and to time it with an incoming tide just feels like cheating. That's the only reason that keeps me from going back again (did it in 2009 and 2010.)

I haven't done either, but if you want to do the GFT this is the year. They are going all out for the 25th and registrations are up significantly over past years. There is talk that the race may move to the spring, or fold altogether if the 2016 registrations fall back to where they have been the last few years.

This is the exact reason why I'd probably do GF than repeating B2B (I've done the half twice). They used to do B2B on the first Saturday of November (same weekend as IMFL), but now do it on the last Saturday of October, a week earlier. Either way, it's almost bound to be balls freezing cold in the morning, and usually warms up to a nice temperature by mid-day. I seriously hate being cold on the bike, but some people don't mind it too much.