Two different olive cultivars grown under a high-density hedgerow system were studied to compare their fruiting and branch architecture features and to determine the possibility to use ‘Calatina’ olive trees for intensive plantings, as a local alternative to the international reference ‘Arbequina’. Weights of two-year-old branches, fruits and leaves were recorded to estimate the growth partitioning. Growth and architectural parameters, such as shoot length, vector and diameter, branching angle, branch total length, height, width, area, and branching frequency, were determined by digital image analysis. Digital images of the fruits were also used to estimate fruit maturation by peel color analysis. Whole branch and fruit crop weights were similar in the ‘Arbequina’ and ‘Calatina’, while the latter had a greater fruit/leaf ratio, showing a higher production efficiency than ‘Arbequina’. Fruits were fewer but bigger in ‘Calatina’ than in ‘Arbequina’, suggesting an advantage for both trunk-shaking and straddle machine harvesting in the Sicilian cultivar. Leaf/wood ratio, branching frequency and branching angle were similar in the two cultivars. ‘Calatina’ shoots exhibited a greater bending degree than those of ‘Arbequina’ and this trait particularly favors straddle harvesting. In addition to many similarities between the two cultivars, the present study indicates that ‘Calatina’ is more efficient in terms of yield and harvesting than ‘Arbequina’. This qualifies ‘Calatina’ as a superior, yield-efficient olive cultivar suitable for intensive hedgerow plantings to be harvested with straddle or side-by-side trunk shaker machines.