Why choose a location when your house have wheels? If you aren't big on amenities:

Sites:

http://cheaprvliving.com/

http://carliving.info/

Community:

http://www.cheaprvlivingforum.com/

Book:

How to Live in a Car, Van or RV--And Get Out of Debt, Travel and Find True Freedom

I live in Los Angeles and it's great. Beach and mountains are close by. Great night life. And yes, it is warm/sunny throughout most of the year.

I'm in my 20's too so if you do decide to move out here, you'll already have someone who can show you around :)

I did this. My best friend had died, I couldent stand to drive around my home town seeing all the places we had spent time, the movie theaters, malls, parks, etc. Finally I decided I was buying an RV and heading... north. I left with no plan other than to reach the farthest point north possible. I traveled up the Al-Can highway and eventually hit the gates of the artic national park in Alaska, then faced with turning back or finding a place to winter a native woman at a hot springs suggested Sitka Alaska, an island 14hrs by ferry off the coast of canada.

Sitka isn't what you'd expect, its climate is temprate rainforest, it only gets two weeks of snow a year (so not too cold) but it gets tons of rain a year. On the plus side, its the most beautiful place on earth. crystal clear water, bears, whales, killer whales, otters, moose, waterfalls, a huge volcano, tree covered isolated islands jutting out of the surf, and the aurora from around late september/October on. after three years on the island family problems back home forced me to leave my wooded home, I miss it tremendously, but if I had to do it all over again there isn't a place on earth I'd rather go.

as a side note, after a year your a resident, you can catch hundreds of pounds of salmon and halibut, shoot more deer, elk, carabu and moose than you could possibly ever eat, get 10,000 board feet of lumber from the forest, and the oil companies pay you just to live there, on top of all of that you can qualify for rural development loans if you ever decided to set down roots.

I know Alaska was probably not on your top 10 of warmer places to consider, but then you probably didn't know about the south west island chain. btw they surf there all year round.

Top of my list would be San Diego, charleston, SC, or anywhere in South America.

I live in Chicago, too...moved here two years ago from NJ/NYC. Needless to say, I feel you on wanting to go somewhere warm all year round. I guess I feel you on wanting to go somewhere a little more Paleo-friendly, as well. While Chicago is insanely "foodie", it's way too easy to go against a healthy, eating lifestyle. I'll be looking for some sort of the same in the not-too-distant future, so I'm sending you good vibes!

Hey Ryan,

Come check out Richmond, VA some time. It's about 30 miles across the metro area each way and on all sides surrounded by rural farmland. We have multiple farmer's markets open each weekend and a great "foodie" culture in the city. It's a perfect mix of big city and country living. Easy access to hiking trails/canoeing/kayaking by the river and only an hour from the mountains. We have all four seasons but rarely drops below +20 degrees.

I once moved from here to Austin, TX on a whim in a similar state of mind and moved back 2 months later. Could be something special about the Old Dominion or you may discover there's just no place like home.

Good luck!

Do what makes you happy for sure. Trying to force yourself to do something/be something that is not true for you only leads to great unhappiness. Follow your inner-voice. As far as favorite places- Oahu- I lived there for a few years and LOVED it. The island is such a healing place...Honolulu is a bit crazy and dirty, but anywhere else on the island is awesome. There is a Whole Foods and Down to Earth and a bunch of other health food stores and great farmer's markets. Second choice due to needing warm weather would be LA- but I would live in Venice, Santa Monica, or Malibu if you can afford it. There is a huge health movement down there and tons to do. Third choice, though on the cold side, Santa Cruz- Great surfing and tons of natural foods stores and farmer's markets. Huge alternative scene. Beautiful hiking and places to bike. Makes up for the weather.
One more note- if you like warmth- don't sacrifice it! I did, and am currently living in San Francisco. No matter how great this area is, the weather is miserable and so am I. I thrive on warmth and sunlight. Working on getting out of here!!! Good luck!

I did that 5 years ago. Packed up from BFE Ohio (yeah I lived in the boonies with my parents) and drove out to LA. Spent the last 5 years in the San Fernando Valley. Just moved again recently half way between LA and Palm Springs, CA. Got the mountains on one side and the desert on the other. Much quieter than the city of Angels and I love that. Not as much traffic either which is also a blessing. Golf courses, hiking trails and bike paths everywhere. California really is the land of opportunity. I came here because the Midwest was losing jobs left and right and got hired right away. The job craze dwindled, but there is still so much of life that you can create here because Cali is just that kind of place. The only question I guess is whether or not 110 degrees is hot enough for ya? Although it can get pretty cold at night depending on where you live. :)

Colorado has just as many days of sunshine as California! Come to the Rocky Mountains!