Derrick Said:

When should I request a leave of absence to travel?

We Answered:

I would recommend in beginning of april. Say that everything is already paid for or partially paid and there is no way that you are backing out of it cos if backing out would result in cash losses. Explain also how you have selected the dates according to non-peak season for the company(dun tell them its partially the reason, lie and say that its the main reason for choosing those dates) and you really appreciate what the company have done for you so far and would really like to work for the company again after your trip.

Applying in April would give them bout a month to look for a replacement and for them or you to train your replacement(which might take another month).
DO NOT apply anytime later than early April(earlier than apr is fine).