If you are going to grind a hand rail you should be able to do lots of grinds. Try something easy on the rail like a Miszou, Soul, Royale, or frontside. First you must make sure that you can jump on the rail, a good way to find this out is to jump over it, or (if it's flat) stall on it. Also make sure it's not to steep since this is your first time. When approaching the rail roll slow and crouch low so you can get enough height. Now just go ahead and jump, make sure to watch where you put your skates and stay low and centered on the rail so that you don't fall. Practice one grind repeatedly untill you are sure you can do it almost everytime. Now you can try different grinds.