So big vacations we typically plan two to three years in advance and book as soon as the booking opens for the parts of that holiday. Usually means flights about 12 months before, accommodation usually a bit before then. Something like Disney or a sailing holiday we can book two years in advance as an entire package, which in the EU means we ATOL protected, far safer that far out than booking separate. I have terrible anxiety when booking lots of individual components like a backpacking holiday in Japan that had us staying in half a dozen hotels/apartments, hiring a couple of cars, getting internal flights, prebooking tickets to Sumo and Ghibli and so on, but its essential to get the best prices.

We are still paying for a family holiday in a cottage or villa as our kids are still starting their careers. This I book a year in advance, but we plan the locations far in advance of that and scope out where we want to stay.

As we work from home we can work from our van a fair bit. Earlier in the year we did a tour of wales over three weeks while working part time, later this year we are doing a three week tour of Cornwall/Devon/Somerset. We also get away a few long weekends around the bank holidays. As we stay at adult only sites that are very popular and will sell out quickly around the dates we want to go, these are booked as soon as booking opens for them, usually October the year before.

Booking early gets us far better pricing and we get to go where we want, stay where we want. Plus the planning and research is a big part of the enjoyment for us, its also essential if you want to make the most of a planning heavy holiday like Japan or Disney and not pay through the nose to use a quality planning service.