ISO : Recommendation for my winter beer trip.

Winter, Asheville, moderate temps (relatively speaking), not far from snow activities if so desired

 

As someone from CO, now in Chicago (temporary), I'll throw in a +1 for SD/L.A. - the only downside being public transpo, but San Diego would be my #1 go-to in that period of winter.
A lot of the other places can be dodgy in Jan-Feb, and having tired FL breweries, not as thrilled with the options there (no offense, just sayin').

 

Id say denver. For experience. But if you want to see the human spirit, id say miami. Thst hurricane right is going to ve bad news and months from now, they are going to have a resurgence and a much needed tourism boom to get their area back

 

The key word is winter. So SD it is, great beer, probably the best climate in the states. Id easily go Vt in fall, going to HF in the snow and or icy roads, no. Anything close in Vt is 40 miles away, lots of driving, so too risky in the winter. If I was hell bent on NE hops in the winter I'd opt for Boston.

 

Totally have to consider Richmond VA. Not only can you knock out a lot of great Richmond brewers, but the restaurant and food truck scene would be memorable. Veil sours could possibly be rolling consistently by then too. Being in RVA, you could also spend a day up in DC and hit Ocelot and Aslin. Finally, distro in Richmond is out of sight, so you could pick up decent stuff from other areas as well.

Edit - weather can be a coin flip, but if it's nice, it's pretty good. If it's nasty, it only lasts about two days at a time.

 

Given that your preferences are a) coming in the winter and b) not driving, your options are pretty limited. San Diego is probably your best bet, but the breweries are spread out, so plan to spend a lot on Uber (for example, getting to Lost Abbey will cost you $40+). Asheville is a decent option too, but other than the (many) downtown options you'll still be spending a lot Ubering it to places like Sierra Nevada.

Someone mentioned Richmond, which is a good choice for a short trip, although the weather can get a bit cold.

 

Sierra Nevada from San Diego???
that ain't a day trip
San Diego to Chico is about a10 hour drive

 

OP - with all the advice, looks like you'll need to stay a year!

 

Ha! I was referring to the NC Sierra Nevada from Asheville. Getting to the CA one from San Diego would be an adventure...

 

Add another one to SD +LA, although personally I would probably just stay in San Diego. You have Mikkeller, ale smith plus Stone. The weather is guaranteed to be nice, and, most importantly, you don't have to worry about the fear of driving in snow (since you mentioned you were concerned about driving, I presume this means you have never driven in snow). It is also a great dining and cocktail scene as well.

St Louis would also be a viable option with side project, among others.

Speaking as someone from Minnesota, the midwest would be a nightmare for you in the winter as someone that is not adept at driving in snow. A trip from Chicago to Minneapolis (even ducking down to Decorah, IA for Toppling Goliath) would be fantastic (and in that timeframe you may even be able to catch the big opening of TG's new brewery with big beers flowing there) but too unpredictable in the winter. I35 running back up to Minneapolis from Iowa can be pretty hairy even as a seasoned driver as snow tends to blow across the highway like crazy because its just a big flat plain the entire way. Minneapolis has great snow removal, but when it snows it REALLY snows and is very unpredictable from year to year. A trip of this nature would be great, however, in the summertime and very easily done on your budget.

 

I have no issues with Colorado in the winter but only with the caveat that I would stick to one area, you don't know what the weather will bring you. There are no promises that if Denver is your hub, you'll be able to make it to Glenwood Springs for Casey. Or even up to Fort Collins or Boulder for that matter. You probably will be able to but just never know. Are you willing to deal with that?