Holiday Harbor Nights is a special event in the Loews Portofino Bay Hotel's Harbor Nights event series and generally takes place the day after Thanksgiving (the last Friday in November). The experience is set outside in the resort's Harbor Piazza. There is an indoor space available, if it looks like it's going to be too cold or rainy on the night of the event.

The Harbor Nights series feature wine, small plate food samples, and live music in an all you care to enjoy setting. There are two ticket levels for the Harbor Nights events. The first is a general "strolling" ticket and the second is a VIP level ticket, which includes a reserved seat and a few additional hors d’oeuvres (served table side), along with a couple of exclusive food and wine stations (that are less crowded than the "strolling" stations.

The "holiday" overlay for this event includes the lighting of a holiday tree and a few additional decor elements. The food and wines are somewhat different for each Harbor Nights event — while there is special "holiday" decore, food items stay with an Italian or Mediterranean theme (i.e. theres no Turkey and Stuffing at the event). There may also be a few holiday songs performed by either the live band or the balcony ensconced opera performers throughout the evening.