The Dec. 25 menu is set for Denise Handlarski’s family: Turkey because it’s Christmas. Latkes because it’s Hanukkah.

Ms. Handlarski, a rabbi who lives in Toronto, will be navigating two important markers of the winter holiday season in her household this month when the first night of Hanukkah and Christmas Day converge for the first time since 2005.

The rare double celebration presents a conundrum for some who observe both holidays — which to prioritize, how to decorate and what food to serve.

Those who celebrate both holidays tend to be interfaith families like Ms. Handlarski’s or Jews drawn to the appeal of Christmas and a perfectly decorated tree. But that feeling is not universal. For generations, Judaism has encouraged practitioners to preserve their culture by maintaining a separate religious identity, and Jewish parents have told their children that Santa doesn’t visit them because they’re Jewish.

But some Jews like Ms. Handlarski believe that incorporating other cultures does not contradict Judaism.

“We adapt Judaism to the places and times we are living in,” said Ms. Handlarski, a rabbi at the online community SecularSynagogue.com. She never celebrated Christmas as a child but now does with her non-Jewish husband and their two children.