Amanda, JB Gill and Sam Pinkham tour the Chianti region of Italy which straddles Tuscany and Siena, searching for the best holiday rentals. JB favours a property in Berberino Tavarnelle with a vineyard view and access to the historic town, while Amanda finds a Tuscan property located in the town of Montefioralle. Sam rivals their choices with a Tuscan farmhouse that has access to a shared pool.