Maritime communications are really challenging due to the adverse transmission conditions and the lack of a pre-provided infrastructure for supporting long range connectivity with land. Communications in high seas are usually covered by satellite links that are expensive and lead to high power consumption by the terminals. However, in areas closer to the shore, other communication options have been adopted for different kinds of services such as boat tracking and telemetry, data collection from moored monitoring systems, etc. In these scenarios, technologies such as cellular communications or wireless sensor networks have been employed so far; nevertheless, all of them present different drawbacks mostly related with the coverage and energy-efficiency of the system. Recently, a novel communication paradigm, so-called Low Power-Wide Area Network (LP-WAN) has gained momentum due to its interesting characteristics regarding transmission distances and end-node’s power consumption. The latter may be of great interest for ships with energetic restrictions such as small sailboats, recreational boats, or radio control ships. For that reason, in this work, we present a boat tracking and monitoring system based on LoRa (Long Range), one of the most prominent LP-WAN technologies. We provide a comprehensive overview of this communication solution as well as a discussion addressing its benefits when applied to maritime scenarios. We present the results extracted from a case of study, where real-training sessions of Optimist Class sailboats have been monitored by means of the presented architecture, obtaining good levels of coverage and link-reliability with limited power consumption. A transmission range study is also presented, demonstrating the validity of this proposal for monitoring activities inside the port or maneuvers close to the shore.