A gift of shares listed on a major stock exchange, of mutual funds or of segregated funds sold by life insurance companies is subject to a special tax rate. The donor need only include one-quarter of the capital gain arising from the transfer of the shares instead of the usual one-half.
Canadian tax law makes it much more efficient to donate shares of companies to charities than to sell them and donate the proceeds. Even ignoring brokerage commissions, the good deed pays much better when it is done with shares than with the proceeds of the sale of the shares.
If the donor has cultural property of significance to Canada and donates it to government or to a museum, then the donation is regarded as being at the property's fair market value and no capital gains tax will be payable.
Sometimes it is possible to have one's cake of assets and to eat it too. That happens when a donor makes a gift of property to a charity, transferring what is considered the residual interest in it via a charitable remainder trust or, if the asset is real estate, directly without the use of a trust. The value of the gift will be its discounted present value, that is, what the remainder is estimated to be worth when the charity takes it over. Estimating the value of insurance policies, which are often given, is a modest problem in calculating the present discounted value of a future sum. It is much more difficult to estimate the value of what shares or other property may be worth in the future.
Good intentions have to be distilled through tax law. Where a donor has capital property, a principal residence not subject to capital gains tax, income properties or a spouse and children, giving requires not just an estimation of who should get what, but also a calculation of what it costs to give. That's an investment decision and one that a financial planner can assist in making.