Serenades Choral Travel was founded as Umbrian Serenades in the fall of 2005, by professional singers, voice teachers, and choral conductors, Holly Phares (2006-2011) and Paulo Faustini, after many years performing and working for the Festival dei Due Mondi (Two Worlds) in Spoleto, Italy. Summer 2006 was the program's very first edition. Joseph Flummerfelt was guest conductor from 2010-2015. 

Over the span of 11 summers “Serenaders” performed in the Umbrian towns of Spoleto, Montefalco, Trevi, Bevagna, Spello, Assisi, Orvieto, Perugia, Preci, Norcia, as well as Siena, TuscanyAssistant conductors, Pamela Simpson (2008-2013) and Stephen Schall (2013-2015) were part of the program in Umbria. In 2017 the program ventured into the province of Soria, in the Castile & León region of Spain, and performed in cathedrals and venues in the towns of Soria, Almazán, Calatañazor, Berlanga de Duero and Medinaceli. Summers 2019 and 2022 the program took place in Southeastern Sicily, with concerts the Sicilian Baroque towns of Noto, Ragusa, and Siracusa (Ortigia Island).  In June of 2023, the program will take place in the Italian southern region of Puglia, with a home base of ConversanoDavid Hayes, who currently serves on the Chorus America board of directors, is the conductor of The New York Choral Society, music director of the Mannes Orchestra, and staff conductor of the Curtis Symphony Orchestra, has been the program’s guest conductor since summer 2016 in Umbria, Italy, in Soria, Spain, for summers 2017-18, in Sicily for 2019 and 2022, and Puglia for summer 2023.