In 1740, Dashwood was in Florence with Horace Walpole, Gray, and others, and shortly afterwards, got into trouble with Sir Horace Mann; there he had also made the acquaintance of Lady Mary Wortley-Montagu. By 1743 Horace Walpole was not impressed and described the Dilettanti Society as "a club for which the nominal qualification is having been to Italy, and the real one, being drunk; the two chiefs are Lord Middlesex and Sir Francis Dashwood, who were seldom sober the whole time they were in Italy".