My Kitten (nearly 8mths) has just started going out and she doesnt go far. Shes been
trapped *cough* too lazy to find her way out of the odd garden with high fences which has seen me zoom around my block (i'm in a cul-da-sac with another one joined on the back of ours) in my car, in my pyjamas shouting her and trying to help her and my both times my 2yr old Peanut has rescued her
I had the added advantage of Evie starting to explore the garden during warmer times, so i was able to sit with her most times and generally she never left the garden until a couple of weeks ago.
I am also a bit naughty
on all of my cats/kittens first trip into the garden either i, or OH will make one short loud noise. A bang or something at the bottom of the garden. If they run back into the house, i am happy that they know its their safe place and that until their confidence grows they wont go far away for a while (infact the garden is usually alot to explore for kittens for quite a while lol) and when i got Peanut, he was in a harness at first, just like Gill has Lupin
Now Evie goes a few gardens away, i prefer that she is out late evening (she is not allowed out all night, where as the adults occasionally do) as the roads near me are quieter if not completely empty. I know she doesnt like strangers or noisy situations. I follow her and keep track of her
but my protective stalking of her is getting less and less
shes a baby at home - but cats are well tuned outside!
You'll find your own balance and knowing your area you'll know when to chose the safest time for him to be unleashed in to the big world