Speaking skills are considered to be one of the most important language skills in learning Arabic, especially for Arabic learners. Because speaking is the goal of Arabic learning, either second language or foreign language. In this study, the researcher found several features in learning speaking skills in Nurul Jadid and Al-Masduqiyyah Islamic boarding schools i.e students often get achievements in the field of speaking skills such as be the champion of the scientific debate in Arabic, Arabic speech contest, Arabic story telling contest, Arabic poetry contest, and Arabic olympics. There is a language environment that strongly supports learning Arabic skills. Therefore, the researcher is interested in doing this study.The purpose of this study are: 1) To find out the implementation of learning speaking skills in the probolinggo Islamic boarding schools. 2) To find out the advantages and disadvantages of learning language skills.In this study the researcher used qualitative descriptive methods. The retrieval of data used by the researcher are interviews, observation and documentation.The resuls of this sudy are : 1). The purpose of learning Arabic skills in Nurul Jadid and Al-Masduqiyyah Islamic boarding schools are the same that is to train students to fluently speak Arabic ell according to thr correct rules. 2). The Arabic language learning material in Nurul Jadid Islamic boarding school are : Vocabularies, conversation, Arabic scientific debate, Arabic specch, story telling, reading news and grammar. The Arabic language learning material in Al-Masduqiyyah are : Vocablaries, conversation, muhadharah, mutholaah, and grammar. 3). The learning methods of Arabic language skills in Nurul Jadid and Al-Masduqiyyah Islamic boarding schools are the memorization method, the direct method and samiyyah syafahiyyah method. 4). The learning media in learning Arabic skills in Nurul Jadid Islamic boarding school are Muhawaroh Al Haditsah book, Jurumiyyah book, Imrithi book, Alfiyah book, Amsilatu Tasrifiyyah book, white board, and LCD projector. Meanwhile, the learning media in learning Arabic skills in Al-Masduqiyyah Islamic boarding school are Jami’ul Mufrodat book, Nahwu Wadhih book, Amsilatu tasrifiyyah book, white board and LCD projector. 5). The learning evaluation in learning Arabic skills in Nurul Jadid and Al-Masduqiyyah Islamic boarding schools are weekly evaluation, formative evaluation and summative evaluation.