I potty trained my son at the same exact age. He was definitely ready. We went and picked out a potty seat, underwear, and used M & Ms as his rewards. I definitely recommend potty training in the summer. We actually kept my son completely naked for the whole day. Be ready for a few accidents on the floor, but he was so excited to use the potty and get a treat, he would actually try to go pee about every 5minutes! If you can, try to have a few days where you have nowhere important to be. That way, you can just relax at home and not feel the pressure of stopping at the bathroom if you are out on the road. It is good to start now, because once preschool rolls around, he will have to be more independant - pulling up and down his own pants and underwear, and wiping himself if necessary. When you get ready to start, just go for it. Tell him at night that tomorrow there will be no more diapers. Put him on the potty as soon as he wakes up. If he wants to just sit there, then great. And by the way, with boys, I believe it is easier to teach them sitting down first - then they can stand after they get the hang of it. Most importantly - don't get upset if it doesn;t work right away. Be patient. He will feel your emotions. And eventually, we ALL learn to use the potty! Good luck!