I wore a size 8.5 in the galileo and it was rediculously tight, should i go with a 9 in this shoe?

Most people find the Galileo to fit more snugly that the A.V. Check out my review for advice on fitting these-i've been wearing them for over 10 years thru the various incarnations and have never changed my size.

i tried both of these shoes on tonight and decided to go with the anasazi. however I wore a 7.5 in the galileo and a 7 in the anasazi. I'd recommend trying them on as they are different fits, but that's just my two cents

Probably. Since they are comparable models within the same brand I'm sure the sizing is pretty close. If the 8.5 were too tight then yea definitely go up. Although finding a local vendor that has them would be good so you can actually try them on. Anasazis are found almost everywhere. Try them out in person if you can then come back online and get a better deal!