Gioachino Rossini (1792–1868) occupies a prominent place in nineteenth-century Italian vocal music, yet the interpretative and compositional importance of his post-operatic songs merits sustained attention alongside his celebrated operas. This study examines the three-song vocal cycle La regata veneziana (“The Venetian Regatta”), comprising Anzoleta avanti la regata, Anzoleta co passa la regata, and Anzoleta dopo la regata. Setting Venetian-dialect poetry by Francesco Maria Piave, the songs depict successive moments in a rowing competition through the changing emotional perspective of Anzoleta, who watches and encourages her beloved, Momolo. The article investigates how Rossini coordinates sectional design, recurring melodic motives, rhythmic figures, tonal movement, chromatic inflection, and piano accompaniment to connect three contrasting dramatic situations. Through comparative examination of the songs and selected notated excerpts, the discussion identifies relationships between formal continuity and expressive differentiation, particularly the recurrence and transformation of descending figures, repeated notes, and melodic leaps. Attention is also given to vocal phrasing, the articulation of Venetian words, and the collaborative responsibilities of singer and pianist. Placing the cycle in the context of Rossini’s later vocal output clarifies its distinction from the separate regatta-themed duet included in Soirées musicales. The study argues that the cycle’s artistic coherence emerges from an interaction of dramatic progression and recurring musical material rather than from surface similarity alone. Its findings offer a score-oriented basis for the interpretation and teaching of Rossini’s chamber vocal repertoire.