The aim of this study was to assess the impact of some viticultural practices (VP) and winemaking technologies (WT) on phenolic composition and sensory characteristics of Negroamaro wines produced in Apulia, Southern Italy. Among VP, two soil management (cover crop and soil tillage) and two training systems (bilateral cordon and unilateral cordon) were compared, whereas among WT, three vinifications were tested: control (traditional, 7 days of maceration at 25 °C with two daily punching-down), cryomaceration (24 h at 0 °C using dry ice) and ultrasound (37 kHz, 150 W, 15 min at 30 °C). Results showed that cover cropping decreased the concentration of flavonoids, whereas bilateral cordon training led to an increase of flavonoids and total polyphenols. Among technologies applied, the cryomaceration led to enrichment in anthocyanins and to impoverishment in total polyphenols, whereas ultrasound treatment improved the extraction of all phenol classes. Cryomacerated wines from the combination soil tillage and unilateral cordon were characterised by the best olfactory and gustatory sensory characteristics. Cryomaceration increased the notes of soft fruits and liquorice, whereas ultrasonic treatment did increase descriptors of violet, soft fruits and black pepper.