The North American Free Trade Agreement NAFTA) increasingly looks like a “one shot” deal with little of the ongoing deepening of economic relationship expected at the time of its negotiation and no provisions for ongoing negotiations. As a result, alternative-trading arrangements may provide an opportunity to move the North American Trade agenda forward. The Free Trade Area of the Americas (FTAA) is one alternative, however,it is an extremely ambitious undertaking bringing together a large number of very divergent economies in terms of size, stage of economic development, economic performance and economic philosophy. This increases the complexity of negotiations and the probability of failure. The paper outlines the major areas where negotiations are likely to be difficult and provides suggestions regarding what has been learned from the NAFTA experience that is relevant to the FTAA.