Italian Neighbors by Tim Parks — Parks's account of settling in the Veneto captures the textures of daily Italian life that apply across northern and central Italy. Useful background for understanding the rhythms of a mid-sized Italian city like Ancona.
Le Marche (various guides) — The Marche is underrepresented in English-language travel writing; Italian guides from the Touring Club Italiano cover the region thoroughly, including the Conero, the inland hill towns, and the coast.
The Architecture of the Italian Renaissance by Peter Murray — Covers the broader Renaissance context for the artistic and architectural heritage found throughout the Marche, including the work of Luciano Laurana (who designed the Ducal Palace in Urbino, a day trip from Ancona) and the Dalmatian sculptors active along the Adriatic.
Italian Wines by Gambero Rosso / various — Any comprehensive Italian wine guide covering the Marche will explain the Verdicchio dei Castelli di Jesi and Rosso Conero denominations. The Slow Wine guide gives good producer-level detail if you want to seek out specific bottles while in the region.