The country singer took the pretty brunette, known only as Mary, as his date to the CMA Awards in November, and again to the CMT Artists of the Year last month, and now it appears their relationship is heating up after the couple jetted off on vacation together.
The pair was photographed strolling along a dirt path to the ocean on December 27th and, in another image, Chesney's alleged new lover is snapped resting her hand on the star's backside.
A source tells People magazine, "They are getting to know each other."
The 44 year old was married to actress Renee Zellweger for four months before their union was annulled in 2005.
Photo Credit Splash News