When/how do you decide to make your trip?

We always go in May because of the weather and the basketball playoffs. Lately we have have scheduled a second trip in late August / early September. My job is flexible on time off but my wife works in cosmetics and is unable to take off when they are in gift. The last three years I have gone on a father/son road trip in November but this year we moved it up to second week of October because of iffy weather in November.

Mark

 

about 2 weeks after I get back?, there's this itch at the base of my skull and I know it's time to book rooms and airfare
...2-3 weeks later I'm usually back in town

 

We try to go in conjunction with birthdays twice a year (Jan and Sept) and then squeeze in another trip somewhere in between usually in April or May.

 

Try to arrange the trips 6 months apart and possibly during a week that has a holiday to save vacation days.
We also monitor the airfare. Once they start releasing with the dates and time we want we jump on it.