If I sell my shares for less than the original price, can I claim a capital loss?

Q.

I am 59 years of age and I have been accumulating shares since 1987. I plan to retire in two to three years and sell some of my shares to fund a three month overseas trip. I read on the weekend that I can sell my shares to my wife. If the market price is less than the cost of the shares when I bought them, I can claim a capital loss to offset any capital gains when I retire and take that trip. Is this legal?

You can sell your shares to anybody you choose but for capital gains tax purposes the ATO will assume they have been transferred at market value. Have you thought of transferring them to a self managed superannuation fund? If the sole purpose of selling the shares is to provide the cash for an overseas trip I wonder why you wish to sell them to your wife because if you did that she would need to sell them to raise the necessary cash.