In the storied streets of Edinburgh, where history has long been delivered in hushed and reverent tones, one tour guide is quietly challenging the assumption that learning must be solemn to be serious. By treating art history the way a knowledgeable friend might — with humor, candor, and a willingness to ask irreverent questions — this guide is revealing something older cultures once knew: that laughter and wisdom have never truly been opposites. The attention this approach is drawing suggests that heritage tourism, and perhaps education more broadly, may be ready to remember that truth.