In 2017, Stirling released the Christmas album Warmer in the Winter and toured that December.

Ahead of this tour, Stirling noted in an interview how her fans encouraged her to make this an annual event.

It began in Fresno, California, on 19 November and concluded on December 23 in Fort Myers, Florida.

The following set list is representative of the show in Fort Lauderdale, Florida, on December 21, 2019.

Music Connection wrote positively about her stop in Rochester, citing the mixture of songs, quality of dancing and the fun elements of the show.