If I waited until everything was done, I'd never get a break. At some point, I just pick the week, and go. I spend waay too much time sitting at a computer, so I like to be active and low tech on holidays. If we're still within cellphone range, we haven't gone far enough from 'civilisation'. The most sophisticated electronica used is a handheld game one of the kids might bring along, or maybe the car - but even that gets left home sometimes. My favourite vacation is to load up the bicycle with a minimum of basics and pedal off into the sunrise. In the midst of tax season especially, I daydream of selling everything and being a bicycle nomad for the rest of my life. No matter how long the holiday, it's always too short.
I've been daydreaming of doing a cross-country bike trip myself... once in a while I run into bicycle nomads on the trails around here... one guy in particular had an impressive rig: recumbent bike with 2 trailers. I talked to him for a bit; he had been all over Canada and the US, and had been on the road for years. Meanwhile, I have a "vacation" coming up. I'm heading to Los Angeles to attend the Siggraph computer graphics conference. I'm looking forward to that, and it's especially nice that the school where I teach is paying for travel and registration and the company I work for is letting me go w/o using vacation time. I'm also having a premiere party for a short film I made while I'm out there. So lots of business-related stuff, but it will still be a big vacation for me!
I'll be going to New Zealand very soon (mid-October!!) for 4 weeks. I'm hoping for fine weather and a resurgence of the US dollar.