Wilson trained as an artist at the Trustees' Academy in Edinburgh and at the Royal Academy Schools in London. He was successful and respected as both a practicing artist and an art dealer. His landscape paintings reflect his Italian voyages, literally in the case of his Italian vistas, but also figuratively in his classicising use of suffused light and stillness that he brought to his landscapes painted at home. After eight years as master of the Trustees' Academy in Edinburgh, Wilson settled in Italy in 1826, where his chief activity was picture dealing. Some of the treasures that now form the National Gallery of Scotland’s collection passed through his hands, including Van Dyck’s Lomellini Family (NG 120) and Jacopo Bassano's Adoration of the Kings (NG 100).