This study investigated the establishment of 16 species of herbaceous, annual or short-lived perennial forbs, by sowing two different mixes in five experimental fields around Greece. The study aimed to examine the feasibility of establishing a naturalistic herbaceous community, as a more sustainable and visually enhancing alternative for landscape management at archaeological sites. Two seed mixes were designed with plant species selected from the pool of taxa recorded in seven archaeological sites around Greece. The mixes were sown in experimental plots during two sowing seasons: autumn and spring. Measurements were taken two months after each sowing period and included counting the number of seedlings for each species. Seedling density and emergence percentage for each species were calculated. Cutting was applied in one experimental field as a weed control method. Before field trials, seed germination tests were conducted under laboratory conditions. The most successful species regarding field establishment were Medicago polymorpha, Trifolium subterraneum and Calendula arvensis. Higher seedling densities (70 to 267 seedlings m−2) were recorded in autumn-sown plots compared to spring-sown plots (50 to 153 seedlings m−2). Cutting had a positive effect on weed control, reducing weed infestation from 72% in untreated plots to 25% in treated plots, while simultaneously it promoted seedling survival to 218 seedlings m−2 from 97 seedlings m−2 in untreated plots. The study proved that species which showed great adaptability to experimental field conditions could be successfully used to establish herbaceous meadows at archaeological sites.