I travelled around the country last year, partly in search of this answer. I've yet to visit Arizona (that is planned for this fall tho), but the place I came back to was the mountains. More specifically, the Rockies. The Denver area (all the way to Boulder and even Fort Collins) is a cyclist's paradise. I've yet to visit another place that has more bike lanes, shoulders, and trails to ride on than this area (Boulder especially), and with the mountains to constantly look at and climb up to, it hardly gets better for me. I haven't spent much time here in winter (except to snowboard), but from the sound of it, the winters are way better here than they are in my home state (OK). With the dry air and low winds (relatively) it sounds like it wouldn't be difficult to cycle year round here (maybe someone who has lived here for a bit can chime in about that?). Basically, if you think Nashville has a great climate, you will absolutely love Denver.
Also, if you don't like to be around a lot of people, and you don't mind some actual cold winters, western Montana seems to be a great place (it's stunningly beautiful). As far as simple beautiful terrain goes, I thought eastern Utah (the scenic drive to Moab) was one of the best areas I've been to. Santa Fe is also a very cool town with good weather and cycling. I would avoid most of the northwest. Great place when the sun shines and you can still train when it doesn't, but the lack of sunshine would likely really mess with someone who likes to be outdoors and isn't used to not having it (there are dry, sunny places tho, Bend is supposed to be pretty amazing). Couer d'Alene is beautiful, but I had a harder time getting a good conversation with people there than in NYC. San Francisco is supposed to be one of the best cities in the world to live in if you can afford it.
To narrow it down tho, if you want pure warm weather and lots of shoulder and bike lanes for cycling year round, northern Florida is hard to beat. The panhandle and Gainesville in particular have great cycling communities. But, to be close to a big airport, Clermont (just outside of Orlando) would be what you were looking for. With a lot of ITU triathletes (as well as world class track stars) it has a great cycling and running vibe. Plus, the pools around Florida can be really cheap (I was paying $2/swim at a neighborhood lap pool in Gainesville).
The other close to a big airport city that would be good for cycling is, of course, San Diego. Pretty much any city along the southern california coast or even out closer to the mountains seems to be pretty amazing. Provided that it is far enough from places like LA that it isn't overly crowded.
I've also yet to visit towns like Madison, WI, and Minneapolis, MN, but I think those are likely too cold at times for your (and mine) preference. New Hampshire (white mountains), Vermont, and Maine are all spectacular areas, but then again, likely too cold in winter.
Chattanooga could also be a good candidate, as its only a couple hours away from the ATL airport, and it has some really beautiful places to ride.
Hope some of all this random info helps. Let me know if you have questions about a particular area. I've spent time cycling in most.
-Bryan Journey
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