I would suggest that no Florida city should make the list. Our summer weather (all 4 to 5 months of it) alone is enough to disqualify any city not in the panhandle.
But if you are going to pick one, it would have to be Clermont (if you are going to elevate Clermont to true "city" status). One of the few places in the state to get hills, lots of access to paved trails, a disproportionately huge endurance sport population, and, of course, most importantly, the clay loop.
As an added bonus, you get to come across world class athletes. Justin Gatlin and a bunch of other top tier sprinters train at the NTC, many world class and Olympic triathletes winter there, and you will get the occasional world class distance runner out there any given weekend (I got to chat with Ritz, Shadrack Biwott and Kevin Hanson for a few minute this weekend as they have been training on the clay loop for some heat adapation in advance of Boston, and Des Linden did the same last year).