It's kind of a tough one. Sure snowboarding is always a blast but as NRG said, how often do you get a free trip to Jamaica. Even some of the most die hard winter addicts I know take a week off in middle of the winter to go to a sunny local. Also, end of December to the first week January tend to not be the prime parts of the season most years. Usually by the second or third week if January it's really pouring on. So you could miss the beginning of the good stuff but I doubt it would be very much.
Plus, girls in bikini's, snorkeling, scuba diving, surfing don't suck. These are vacation spots that tons of people go on, a lot of them single and a lot of them female. You can have the perfect relationship for the better part of a week and never see her again.