As long as the market remains strong and because the CARES Act is still in effect, 2021 is the year to consider making a significant charitable gift. However, first and foremost, always talk to your tax advisor before making any substantial charitable gift.
Gifting appreciated stock that you have held for more than a year allows you to deduct the full fair market value on the date of the gift while avoiding paying capital gains tax. The gift may be contributed to a donor advised fund which can be used over time to support nonprofit organizations and charitable cause you care about.
Bunching Your Gift
Making a large gift of appreciated stock in 2021 would allow you to take advantage of “bunching” your gift. For example, you contribute stock (valued at more than $12,550 if you file as an individual or $25,100 if you file jointly) to your donor advised fund in 2021, itemize your deductions, and receive a tax deduction for the full gift on your 2021 tax return. In 2022, take the standard deduction and use your donor advised fund to make 2022 annual gifts. Below is an example of "bunching."
An example of bunching your charitable contributions.