Strategy 1: Donate Appreciated Securities Instead of Cash

This is one of the most powerful—and often underused—strategies in charitable planning. Instead of selling appreciated stock, paying capital-gains tax, and then donating cash, you may be able to donate the stock directly to a qualified charity or to a Donor-Advised Fund.

Potential result: When the rules are satisfied, you may receive a charitable deduction based on the fair market value of qualifying long-term appreciated property while avoiding recognition of the built-in capital gain that would have resulted from a taxable sale.

Illustration: If you donate $50,000 of qualifying appreciated stock that you originally purchased for $10,000, and a hypothetical taxable sale would have generated a $40,000 long-term capital gain, avoiding a 20% federal capital-gains tax on that gain could represent $8,000 of avoided federal capital-gains tax. A separate charitable deduction may also be available, subject to AGI limits, the 2026 charitable deduction floor, holding-period rules, valuation rules, and the recipient organization.

Strategy 2: Donor-Advised Fund (DAF) for Bunching

For 2026, the standard deduction is $16,100 for single filers and $32,200 for married couples filing jointly. If your allowable itemized deductions do not exceed your standard deduction by enough to create a meaningful benefit, bunching several years of planned charitable contributions into one year may increase the tax value of your giving.

How it works: You contribute two or more years of planned charitable gifts to a DAF in one tax year. If the contribution is deductible, you claim the charitable deduction in the contribution year, subject to applicable limits. The DAF can then recommend grants to eligible charities over time.

For 2026, the state and local tax (SALT) deduction limit is generally $40,400 ($20,200 if married filing separately), subject to a phase-down for taxpayers above the applicable modified AGI threshold. Your actual itemized-deduction picture therefore needs to be modeled using your specific income, mortgage interest, taxes, charitable gifts, and other allowable deductions.

Strategy 3: Qualified Charitable Distribution (QCD)

If you are age 70½ or older and have an eligible IRA, you may be able to make a Qualified Charitable Distribution directly from the IRA to an eligible charity. For 2026, the annual QCD exclusion limit is $111,000 per eligible individual.

A qualifying QCD can count toward a Required Minimum Distribution (RMD) when applicable while the qualifying amount is excluded from taxable income. That can be more valuable than taking a taxable IRA distribution and then making a separate cash gift because reducing adjusted gross income may affect other tax calculations. A QCD is not also claimed as a charitable contribution deduction.

Strategy 4: Charitable Remainder Trust (CRT)

A Charitable Remainder Trust can allow you to transfer a large asset—often appreciated securities or real estate—to an irrevocable trust, potentially receive an immediate partial charitable deduction, receive an income stream for life or a fixed term, and leave the remaining trust assets to charity at the end of the trust term.

This strategy can be especially relevant for highly appreciated assets with a low cost basis, but CRTs are complex. The tax treatment depends on trust structure, payout terms, asset type, valuation, timing, and the donor’s individual circumstances.

Strategy 5: Conservation Easements

If you own real property with conservation, historic, or agricultural value, a qualified conservation contribution may create a charitable deduction when strict federal requirements are met. The amount of any deduction depends heavily on valuation and compliance.

Proceed carefully: The IRS closely scrutinizes abusive and syndicated conservation-easement transactions. Any conservation-easement strategy should be reviewed by qualified tax and legal professionals and supported by a qualified appraisal when required.