Tertiary syphilis is now a rare disease in Europe, mainly as a result of occasional antibiotherapy for concomitant infections. However early syphilis is rising in USA and Germany, and it is necessary to maintain an high level of knowledge and suspicion to achieve a diagnosis in the tertiary stage of the disease. In this report two patients with benign tertiary syphilis are described. The first one is a 55-year-old female with erythemato-violaceous annular scaling plaques on the right buttock and scapula and on both thighs, which had a negative and then a low VDRL titer. The second case is a 33-year-old mentally handicapped female with erythematous plaques, with psoriasiform scaling in the trunk and well defined crusted ulcers on the face, which also had negative VDRL. Biopsy of the skin lesions revealed plasmocytic infiltrate with endothelial swelling without granulomas and with negative silver stains in both patients. The investigation for cardiovascular and neurological involvement was negative in both patients. Diagnosis of tertiary syphilis can be difficult as clinical pictures can be misleading, similar to other granulomatous diseases, and serological titers can be low or negative. We recall the necessity of ruling out neurological and cardiac involvement in this stage of syphilis. These cases are reported as a reminder of the possibility of syphilis, so that new cases are not misdiagnosed and mistreated as other diseases.