Many U.S. insurers are starting to experiment with building medical tourism into their health plans. Demand for private insurance plans that cover medical tourism is likely to increase in the wake of the U.S. recent health care legislation (aka Obamacare). Given this forecasted increase in private insurance plans incorporating medical tourism, this is the perfect time to seriously examine the legal and ethical issues raised by medical tourism involving private health insurance, the goal of this chapter. It begins by briefly describing the growing private insurance medical tourism industry and the possible forms various insurance plans incorporating medical tourism might take. It then revisits the issues related to quality and liability discussed in the last two chapters and how the issues and their regulation are inflected in the private insurance medical tourism context. Finally, it examines questions relating to the ethics and regulation of private insurance plan design.