The first thing that my father-in-law said to me when I got to his house on Thanksgiving was, "Stay off the computer. Be with the family." If he really wanted me offline, he could have turned off the Wi-Fi. But he didn't. And I met him halfway by sitting down with my mother-in-law and my ThinkPad, and working on the family tree on Ancestry.com. She loved it, and it was a good family-bonding experience.
There are other good ways to gather 'round the Web during the holidays. So if you're going to be with family, and would rather that they keep you company on the Web instead of the alternative--everyone stays off and plays Parcheesi--try these family-friendly Web 2.0 activities:
Like I said, this is my top tip. Fire up Ancestry.com and ask a relative to sit with you and tell the story of his or her family tree. Capture it all on the site. Repeat with other family members and you'll be surprised what you learn. Bonus: Everyone will have something new to talk about, instead of criticizing your job, clothing, child-rearing skills, etc. See also: Geni, Kindo, and Amiglia.
Before you go on your trip, upload a bunch of old family photos into your Flickr account. Then, when you're in need of an online group activity, sit down and start tagging photos with names, events, and so on.
If you have old film negatives, slides, and prints you want to work with, check out ScanCafe, which offers very good prices for a scanning service. It takes a while to get your images back, though.
Once you've got your photos online, consider creating a family photo book with a service like Blurb.
Bonus photo activity: Give the gift of a digital picture frame (like this unit from Ceiva) that supports over-the-Web access. Upload cute pics of the kids at least once a week.
Sick of the three cheesy CDs your uncle is playing on the stereo? Hook your laptop up to the aux in (bring a 3.5mm mini to RCA interconnect cable with you), fire up Pandora, search for "Christmas," and you're off. You'll have to tell Pandora that yes, you know it would rather search by artist than genre, but once you do so it will display several Christmas playlists for you to choose from. Also works for "Hanukkah." The same trick works on Last.fm.
If you have kids and you're visiting your parents, this will be an easy sell: Set up their PC or Mac with a Webcam and Skype (download) and teach them how to use it. Then when they kvetch about you never visiting with the kid(s), you can fire up a video chat. It's the green way to keep the family together. (Of course, if you and your parents both have Macs, just use iChat.)
Finally, if all the togetherness gets to you, lock yourself in the den and kill some time playing Flash games. I recommend Kongregate for finding games worth playing. There are even some that can be played by two people, either in co-op mode or one-on-one.
This isn't really a Web 2.0 activity, but when you get roped into fixing or tweaking a family member's computer, especially if the family member is older (a parent), please see my old advice on how to stay sane during and after the fixing process: Insider Secrets: Tech support for your parents.
Thanks to: David Katzmaier, Declan McCullagh, Elinor Mills, and Phil Ryan.