This paper presents a contrastive analysis between selected Tuscan and Portuguese proverbs and their variants; such presence of proverbial variants evokes reflections on the liminality of the proverbial sentence between writing and speech: in fact, the few proverbs that can be translated word for word from Italian to Portuguese regard principally Biblical passages, thus demonstrating the common Christian religion between the two peoples, and Latin maxims, since both languages in contact belong to the Romance family. The proverbial sentences from Giusti’s 1853 collection of Proverbi toscani and Costa’s 1998 Livro dos provérbios portugueses are subdivided between different semantic fields; the selection of coreferential semantic fields from the two collections allows to conjecture shared cultural traits between the two peoples, though Costa observes a cautionary connotation among the maxims he selected, which leads him to ponder on their aristocratic origin, whereas Tuscan adages are mostly related to farming and domestic life.