First, good choice on Chiang Mai over Phuket. I have been to both, and for me CM is by far the best.

As to experiencing the culture - walk! I am not sure when you are going, but if you are going between November and the end of February, the weather will be nice and walkable.

I suggest walking around Old Town (inside the moat) - culture everywhere. Just some thoughts (they are all close to each other):

1. if you want a massage, there is a place called Lila massage in Old Town, which is a program for Thai women who have been in prison and teaches them a skill they can use outside of prison. I had a foot massage and it was very good. You can get reviews on the Internet.

2.For food, you can go about 500 meters North of Lila massage, to the North Gate area, and cross the main road, and there are a ton of good Thai food places, street food and restaurants. if you saw the Anthony Bourdain CNN show on Chiang Mai, that is one of the places he went to.

3. Then later on you can walk back across the street to the North Gate Jazz Club. it is a tiny place, and I am not sure you will see the reincarnation of Charlie Parker, but you will see a nice mix of Thai and westerners listening to live music, and take in a bit of the Thai evening street scene.

Have fun!