Viticulture has historically been an important part of the social and economic life in the Mediterranean, while wine is reckoned among the oldest documented trades. The aim of the study is to record, evaluate and analyze spatial data from historical sources in order to gain insights into the dynamics of the viticultural landscape from the beginning of the Ottoman period to the present day. The study was based on (a) three historical maps published in 1885, 1942 and 1969, (b) records from historical surveys—two from the Ottoman period (1572 fiscal survey, 1832/33 property survey) and the British agricultural census of 1931, (c) present-day records from the vineyard survey of 2009 carried out by the Republic of Cyprus. In the beginning of the study period the center of viticulture was well established within the area of the southern and eastern slopes of Troodos massif. The vineyards expanded mainly around the same growing area until WW2 when they gradually began to be relocated in southwest direction to lower altitudes. This long-term trajectory of spatial patterns was driven by external demand for the product but also by the interplay of environmental, topographic and cultural factors, as well as by the state’s policy framework which largely reflected long-term Mediterranean-wide patterns.