Alternative investments, such as hedge funds, venture capital, and private equity, can improve portfolio performance, especially for long-term institutional and high net worth individual investors. Difficulties arise when rebalancing a portfolio that includes alternative investments due to the nature of the commitments. Transaction costs can be sizable and money flows are restricted by illiquid markets, covenants, and related restrictions. Following a review of the pros and cons of including alternative investments in a traditional portfolio, the authors show the intrinsic advantages of a multi-period asset allocation strategy and present an optimizing approach for addressing transaction costs.