Tire size V towing V regearing

I'm looking at adding 33" tires to my DCLB TRD Sport. My wheeling is generally on dry logging roads and trails - think high desert, not sand. But its also a daily driver, so nothing crazy. I tow about 5,000 pounds. If I get 33's will I need to regear?

 

Mine are 31.65" (265/75/16) and I tow right around 5k. For me it's fine but the taco doesn't like the mountain passes.

 

I'd like to know this as well...

 

3.73s with 33s aren't bad. Towing with 3.73s does suck. If you go with 4.56s and tow on the highway while on '4' you will be running 3k+ rpms but it will be a lot better to tow with. Try to find some 4.10s if you are dead set on 33s.