Enotourism has emerged as a promising, sustainable type of tourism that can provide many benefits for local, regional, and national economies. This study critically describes the current situation of the newly-introduced enotourism sector in Chile, analyses the challenges it faces, and offers possible solutions to overcome such challenges. Chile is the eighth wine-producing country in the world, and the first among New World wine regions. Due to the existence of a variety of good-quality wines and unique landscapes, Chile has begun recently to develop its enotourism industry by offering a series of attractive wine routes and wine festivals. Despite recent progress, this nascent industry faces various bottlenecks to its sustainable development, including a still incomplete infrastructure, low human capital, low coordination and governance between relevant public and private companies involved, sustainability issues, inadequate marketing and enotourism-promoting strategies, and lack of synergies with other tourism sectors. Addressing these bottlenecks is particularly important for the Chilean economy, both because at present it loses significant opportunities to generate more income from enotourism, but also because enotourism can contribute to the diversification of the economy, which currently depends heavily on extractive sectors. The suggestions proposed here can also be particularly useful for New World wine-producing countries that may face similar challenges to Chile.