When to Go, When to Return

As I was trying to figure out if I could go out of town during my week off before starting the new gig (answer: no. It’ll just be too stressful, time-wise and money-wise, to try.) one of the important factors was, What day should I leave, and what day should I come back?

When left to my own devices, if I’m going to take a week-long trip, I go Wednesday to Tuesday or Wednesday. I’ve found Wednesday to be pretty consistently the cheapest day of the week to travel. That makes sense, right? If people are taking a long weekend, they leave Thursday or Friday and come back Monday or Tuesday, leaving Wednesday as odd man out of the days of the week club.

But you’re not always taking a whole-week trip. If you’re only going for a long weekend, which pair of days make the most sense? My preference is to leave Friday and come back Monday, because this leaves the full weekend to be somewhere, including a lazy Sunday–nothing ruins a perfectly good Sunday more than having to wake up to an alarm and deal with transit.

What about times to leave? Do you leave in the evening after work or on the morning of the next day? That’s a trade-off between how much money you want to spend (on an extra night in a hotel) versus how much time you want to take at your destination (one extra evening and morning). Plus, there’s that additional thrill of bringing your suitcase with you to work, so everybody knows you’re going out of town, and having to leave the office at a specific time because you’ve got a flight/train/car to catch, and not having to wait several more hours for your vacation to truly begin.

And the one on which I disagree with most people: when do you go back to work? Do you come home and go back to work the very next day? Or do you take one more day off to get back into the swing of things, to do laundry, to go grocery shopping, to get your life back in order? (Most people only consider this for longer trips, but I know at least one person, namely the art director of this site, who thinks it’s required for even a two-day camping trip.) I think, if you really want to make the most of your limited vacation time, you’ve got to dive right back into work, so that you don’t waste a day off on running errands and catching up on a little sleep. I can understand, though, the people who want to take that one extra day. It sort of lets the relaxation of vacation sink in a little deeper. It lets you ease back into life. And hey, if it helps you enjoy the trip more, go for it. It’s your time, after all. You get to pick when you go, and you get to pick when you return, even if that’s a day after you actually come back.

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