When urban agriculture is addressed at a family scale, known as urban gardening, it is assumed as a non-commercial activity where some family members voluntarily take care of the plantation during their free time. If technology is going to be used to support such a process, then the solutions should consider the particularities of these gardeners (e.g., life dynamics and culture) to make them adoptable. The literature reports several urban agriculture experiences in Western countries and Southeast Asia; however, this activity has been poorly explored in South American countries, particularly at a family scale and considering the culture and the affordability of the solutions. This article presents an experience report of urban gardening in Peru, where a prototype of an IoT system and a mobile application were conceived, implemented, and used to support the gardening of vegetables at a family scale, considering the cultural aspects of the gardeners. This experience obtained positive results in terms of tomato production, mainly showing the system’s capability to self-adapt its behavior to consider the cultivation conditions of these urban gardeners. To the best of our knowledge, this is the first IoT system that can be iteratively adjust its behavior to improve the chances of being adopted by a particular end-user population (i.e., gardeners).