WTO (World Tourism Organization) recognizes that adventure tourism is a journey that includes at least two of three elements: (a) physical activity, (b) natural environment; and (c) cultural immersion. With this in mind, the Autonomous Region of Azores, classified as one of the OR (Outermost Regions) by the European Union (EU), meets several of those elements. Therefore, the Archipelago shows several potential for the development of this typology of tourism. However, this insular region faces many challenges. Some of those obstacles are also great opportunities for regional development towards new sustainable models. For example, there is the islands’ geographical location, which enables exceptional territorial development opportunities and growth opportunities. Contextually, the Archipelago’s nine islands afford great variety to the destination, and the tranquil rural landscape fits the perfect framework for unparalleled, charming, and relaxing experiences. Moreover, the Archipelago’s specific characteristics, as its volcanic nature, make the destination a perfect place to be explored. These are just some examples of the region’s potential to develop this typology of tourism, based on nature, and consequently, a vehicle to achieve the so-desired regional sustainability.