Yes, I'll be driving (one of my dogs definitely wouldn't fit under the airplane seat in front of me). As amazing as Key West sounds, I think it's a little too far! There's nothing particularly 'close' unless you consider Lake Michigan beachy in January (ha), but I'll pull up Google Maps and try to look up some routes. Realistically I'm okay with spending a little extra money on this -- I haven't taken any kind of trip for a year so that's not a huge consideration for me. I do love to travel, but I'm tired of traveling alone, so that's been holding me back lately.
I'm not much for night life, but I do appreciate great food and it would be nice to have some people around -- I'm not looking for total isolation! Haha.
Thanks to everybody for your suggestions!
(Also, it's really, REALLY frustrating to answer these prompts for verification every time I post. Quick way to alienate people who just want to participate.)