I'm taking the kids for 3 straight weeks this summer. It's probably one of the longest vacations away from work that I've taken (aside from being between jobs).
In getting organized for this, I've had a calendar printed out and sitting on my desk for the last month. Some dates were pretty firm (we have a camping trip planned on Angel Island for the second week), and others were flexible. For the flexible days I had cut down post-it notes to fit the calendar boxes.
I've been moving, rearranging, and removing ideas daily. Finally what I ended up with was a cultivated list of a half dozen new adventures for them. Then I wrote down a bunch of favorite outings (grouped geographically) on an old drawing easel we had.
We went through and they each picked a favorite from each group. I picked a couple of favorites too. This left us with a list that was a mix of new adventures combined with a bunch of their all-time favorites.
Next we took some butcher paper and drew out our calendar for vacation.
This left us with a great visual not only to do some scheduling, but also one they can check back on for what's coming up tomorrow. Plus now that we have a schedule that they helped create, everyone has ownership over. We left the last week open for the moment to see what opportunities came up as we got closer.
Even with my planning, it wasn't until we all created the calendar that things started to get real for everyone. Now the kids are talking about what we are doing today, tomorrow, and next week. The more they think about these trips, the better chance we have for success when we go (and even getting out of the house)