One if by land, two if by air . . .

By air
If you’re flying, shop around and book early. Possibly look at flying into a nearby, less busy airport. Or fly at off-peak times, early morning or late night.
Arrive early. You will encounter hassles. Not running late on top of that helps minimize stress.
Pack light. Ship gifts ahead. Ask your host if they’ll have basic essentials (shampoo, toothpaste) so you don’t have to lug around all those extras. You can live with using someone else’s brand for a few days!
Prepare ahead: have necessary phone numbers, itineraries, e-ticket printout.
Take quiet toys/games/books to keep kids entertained.
Smile and be pleasant. Remember, airline personnel can be stressed. They’re working up to the last minute—or perhaps even during the holiday. Keep your cool and you’ll get better service.

By land
Driving presents more options (you can take more stuff), but that’s not necessarily a good thing. You can have a tendency to take too much! Make a list before you pack and stick to it.
Wrap gifts when you arrive at the destination or, at the very least, wait to put on bows.
Again, have plenty to keep the kids entertained (DVDs, books, games). But take advantage of the time you’re together, too. You can listen to a family-friendly book on DVD. Our family loved Where the Red Fern Grows, From the Mixed-Up Files of Mrs. Basil E. Frankweiler, and Mrs. Frisby and the Rats of Nimh.
Lower your expectations. It will take you 20% longer to get there than you think. (Gently remind Dad of this fact, too.) Know that your car will be trashed by the time you arrive. You’ll have to make unexpected stops, but that’s really OK. Your parents probably had to stop and let you go potty when you were small!
Take advantage of the togetherness. Talk—have real discussions with your kids. Reward them for good behavior or kindness to one another.

The Wilson family drives everywhere (Branson, MO, the beach at Gulf Shores, AL, South Padre Island, TX, my hometown of Evergreen, CO). We’re conditioned, but we also make the trip itself a time of purpose, instead of simply the means of getting us to the real fun. Of course we have our moments—arguments, getting sick in the car, almost running out of gas—but these simply serve as the backdrop for some of our favorite family stories.

Now we want to hear from you. Won’t you share some of your favorite family travel experiences or tips for making travel a bit easier?