As with the vacation itself, planning for the journey is well worth it. With a little time up front, the relaxation can start sooner.
When we go on vacation, my kids choose several things for their backpacks a few days in advance. But then the backpacks are out of their control and into mine, and I add surprise items. The kids then are not allowed to open their packs until we are either in the air (if we are flying) or on the interstate (if we are driving).
Sometime in the weeks before a trip, I drop by the local dollar store for things like crayons and pads of paper and puzzle books. I also have a stash of small toys that I have picked up from sale tables at toy stores in the back of my closet and I might pull out one of those items for each of the kids. I look through the toy bins at home for items that might have been out-of-sight and out-of-mind for a while, and might seem new again. I put in decks of playing cards or trivia cards, too. If we are flying, I also try to put a couple of small snacks in the packs. When the kids open their packs, it's a surprise what they will find, and usually they are well occupied for the first couple hours.
Books on CD
When our vacation involves driving and when the backpacks lose their allure, I turn to books on tape or CD. Since most of our trips are less than two weeks (and since books on tape or CD can be pricey), I choose titles from the local library knowing we'll be back just in time for the due date. While it can be challenging to find titles that everyone likes, it's worth the effort. The car is absolutely silent.
Before iPods, we had some old cassette players for books on tape, and each of the boys had their own mini-library of stories for a trip. This worked well on planes, too. However, our tape players are long since broken and we haven't quite made it to a MP3 player for each family member. But certainly, downloading stories to MP3 players is an excellent choice for keeping kids occupied.
Classic travel games
I have a vivid memory of a family trip when I was about 10 years old. We were somewhere on the upper penninsula of Michigan, having driven all the way from the desert southwest. Entering our room, I turned back toward our car when I heard a commotion. A boy on vacation with him family was jumping up and down and shouting, "Arizona! I got Arizona!" Clearly the family had been playing the license plate game.
The most fun we have en route to a destination are when we play these family travel games, whether it's the license plate game, or I spy, or whatever. Over the years our family has developed it's own quirks for twenty questions. We call it "Guess the animal," and one of the first questions always is, "Does it taste like chicken?" or, "Does it go well with salsa?" Invariably Sunshine is thinking of a humpback whale, I am thinking of an otter, and Woody is thinking of a chambered nautilus. Alfs is the best at the game and we can almost never guess his animals.
Finding activities while en route doesn't just keep the kids occupied, it also helps the enjoyment of a trip start sooner.