LORELAI (to Richard): You and Mom, you always go out of town this time of year.
RORY: Last year it was the Bahamas.
Last year we discovered it was Richard and Emily’s annual tradition to hold a Christmas party in mid-December. This year we discover another tradition: they go out of town around Christmas time (presumably after the party, but possibly before).
I’m not sure whether they actually go away for Christmas, or if they travel in the week or so before Christmas, and get back in time for the 25th. Richard and Emily spoke about only seeing Lorelai and Rory at Christmas and Easter, so did that just mean attending the Christmas party each year? As that was attended by their friends, it doesn’t seem as if they spent much time together as a family at all, even in the holidays. Perhaps they meant the entire Christmas season – the party, and then Christmas itself.
Richard and Emily went to the Bahamas in December 2000, after Richard had been hospitalised for an angina attack. As Christopher’s parents, Straub and Francine Hayden, live in the Bahamas, it seems very likely the Gilmores either stayed with them, or visited them, during their vacation. It was only a couple of months later that Christopher’s parents come to Hartford just as Christopher arrives for a visit to Stars Hollow, suggesting it was a plan that the elder Gilmores cooked up to bring Lorelai and Christopher together – with devastating results.
The Annotated Gilmore Girls 