Maximizing Limited Vacation Days for Travel – My Dos and Don’ts


Level 2 Member

You have a full time job with limited vacation days. Time is of the essence – but so is enjoying your trip. Cramming a bunch of activities in a short time is great – if you enjoy that. The key is to maximize your free time – in a way that fits your travel style.

If you’ve been doing this for a while, chances are you have your own way already. Still, it’s good to review our habits once in a while to remind ourselves “oh yeah, this is why I’m doing it this way,” and “OK, I see why she’s doing it that way, but here’s why it’s not for me.”

For example, my friend Christine writes about “How to see the World in a Weekend,” as she has done for years. Sadly, I’m a slow jet lag recoverer (I’ve tried many remedies, believe me), so I need more time on the ground to justify the misery.

With that in mind, here are 3 things I do – and 3 things I don’t do. Again, this isn’t to judge anyone else’s ways, I’m just sharing what works for me and why.

My Do #1 – Schedule an easy first day back to work

If possible, don’t schedule anything stressful on your first day back to work. This allows you to stay as long as possible on the trip. I often get back around midnight jet lagged, get no sleep, need to be at work next morning, and by 4pm it’s been almost 24 hours since I got any sleep. Having an easy day helps. I try to be caught up with email in the lounge or elsewhere on the trip – as long as it doesn’t interfere much with the trip.

This is me at 3pm the day after an Asia trip
My Do #2 – Take a red eye

I hate red eyes in economy, but I take a few every year because it gives me half a day (sometimes a full day) more on the trip. I land in the morning and go directly to work. Having an easy day (see above) helps. Of course red eyes on a flat bed is much easier.

My Do #3 – Go somewhere nearby for the weekend

For a while, if I missed Singaporean food (which happens a lot), my first instinct would be to… book a flight to Singapore! OK, that wasn’t the only reason I booked the flight, but you get the point. Thanks to the Ann Arbor DO, I now have an option for Singaporean food 4 hours away. Ann Arbor is no Singapore, but it’s a nice area that gets the job done for a weekend. Obviously this isn’t to discourage going to faraway places, but sometimes we forget the good stuff up the road. In general, I’m a big fan of domestic US travel, from the road trip experience to some of the best scenery in the world.

I went to Blue Ridge Parkway on a weekend trip
My Don’t #1 – Don’t work on a trip

Generally, I don’t mix work and personal travel beyond mandatory emails. I also don’t do any MS, travel planning (except for the trip I’m on), etc. I like being 100% dedicated to the trip.

My Don’t #2 – No short stopovers

On my first big award trip, I had multiple stopovers around 10 hours each, before reaching the destination. I went into the cities for the day, jet lagged and tired. Not for me. If it works for you though, great.

That’s not to say I never do it, and it’s a lot better when jet lag is not involved. But it’s not something I use a lot.

My Don’t #3 – No one-night hotel stays

This is one of those “do it for status/packed schedule but not with your family” things in the hobby. I’m not a fan of constantly checking in and out of hotels, so I like to have 2+ nights in any given place. However, I will allow it for a positioning/returning flight.


What are your Dos and Don’ts for maximizing your limited time off?

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Level 2 Member
For example, my friend Christine writes about “How to see the World in a Weekend,” as she has done for years. Sadly, I’m a slow jet lag recoverer (I’ve tried many remedies, believe me), so I need more time on the ground to justify the misery.
Having acquired a SW Companion Pass earlier this year (and not much left over time to use it THIS year) my wife and I planned a couple of 3 and 4 day weekend trips. It seemed the smart thing to do in order to maximize use of the CP. However, even after a couple of domestic and not-that-far-away-even trips, we've discovered that these don't work well. For us.

If you have to allocate several hours of a day to the AWAY and HOME flights (and don't have tons of power over the flight times offered), a 4 day weekend becomes 2 full days of sight-seeing and some partial days that are rarely ideal. It doesn't help that we're in CLE which has proven to NOT be a very SW-friendly airport. If we didn't have the CP, I wouldn't be flying them at all.

I've crossed off a couple of short trips I had penciled in and extended some of the more important trips to make better use of our time. I had to remember that, while maximizing the use of our SW CP, what good does that do if we are shorting key places or not fully enjoying ourselves? We'll still make good use of this opportunity, it just won't be maximized.


Level 2 Member
Why don't you like red eyes? I always prefer them myself.
I can't speak for the OP, but I hate them because I can't sleep on a plane, one of the main reasons is due to my height. Granted, I have yet to fly in a lay flat seat... I would imagine that would be a different ballgame. But even when I flew domestic first class on a red eye... still couldn't sleep.


Level 2 Member
  1. I have my telecommute day on Monday so I can sleep in a bit if I get in at midnight. Also can do laundry while listening in on a conference call.
  2. If you're blessed with a hub airport, focus on the non-stop options for long weekend getaways.
  3. Catch earliest flight of the day because it is most likely to not be delayed.
  4. Ask boss if you can work extra hours when you get home to offset time used on vacation. Always couch in in terms of being able to meet deadline, or making your absences less noticed by client, etc. I have an agreement that I can offset any vacation take by putting in extra hours during the same pay period. It makes 3-night getaways super easy.
I avoid red-eyes whenever possible. It takes a while for me to recover from those.