How to plan your staff travel trip like a pro

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Finally, it’s here! You’ve been waiting for this since I have started this series. While I am preparing the etiquette guide, and after I have bored you with the rules guide and the general guide, I realized the next logical step is writing this guide on how to plan your staff travel trip using your benefits.

I know, I like to create suspense. It’s what I call “you have to work for it!”. And, also, my tips about how to plan your trip are useless without the first part. You planned for nothing if you had no idea about the visa you need. And, as you’ll see in the next part, everything is useless if you’re a jerk that shouldn’t be left out in society.

So, without further useless words, let’s dig into the best advice to make your trips the best you have while paying almost nothing because you’re one of us. You can read the short version in the following infografic that you can also pin for later, and you can download it from the form at the bottom of the page.

General tips to plan your staff travel trip

1. If possible, travel light with carry-on only.

I cannot emphasize this enough. I would write it in gold letters if I wouldn’t hate the color with all of my strength.

We very rarely travel with a piece of checked baggage, and usually only when it’s a long trip and cannot make it work without like we did in Japan. The flexibility this provides you is unmatched.

Let me present you with some scenarios that may happen to you, and how it goes depending on your checked luggage:

  • Were you offloaded after your first leg?
    Without luggage – Look for your next available flight -> book it -> proceed to gate.
    With luggage – Go out -> do passport control -> have your visa set up (which you need to know before boarding your first leg) -> get your luggage -> check customs -> find your next flight depending on the time you have now -> go to check-in desk with your luggage again -> do the security check again -> do the passport control again -> proceed to gate.
  • Were you denied boarding right from the start?
    Both scenarios highlighted above apply. The only difference here is the less problematic situation of the visa since you were already in that country. Also, if you’re leaving from “home”, it’s easier to go home and take a flight on the next day, and the checked luggage doesn’t help or annoy you in this case, except for, you know, carrying it around.
  • Tight connection and two separate airlines, so the luggage doesn’t automatically go through?
    Without luggage – run between the two gates like there’s no tomorrow.
    With luggage – you cannot book this flight.
    You will never be able to make it to your connection if you have to do the luggage transfer yourself.
    And even if you decide to do this, you have to be very aware of your needed time, and your estimations can be way off the chart. You cannot estimate how long the immigration queue might be, or have no idea on the security checks that might slow you down.
  • Do you have to run to another airport?
    Without luggage – get out of the airport -> get on a taxi -> get to the new airport -> proceed to security -> proceed to passport control -> proceed to the gate
    With luggage – wait for and get your checked luggage -> get out of the airport -> get on a taxi -> get to the new airport -> get to the check-in desk -> proceed to security -> proceed to passport control -> proceed to the gate

Now, spot at least 3 differences between every 2 scenarios. If you have difficulties, close your eyes and imagine doing everything with a huge bag tied to your hand or back

Need to buy luggage as you overused the last one until it broke? Been there! You can get a new one here!

2. Every piece of luggage should have the things important for the person carrying it.

If you have to split the party, you should have everything necessary with you. Pay special attention to important documents, any medicine, cell phones and chargers, laptops (especially the one you use to make reservations) and your badge (that can also be requested at any time).

Also, if you have to get a later flight and you have to spend the night somewhere in Hong Kong, you would want to have YOUR underwear with you, not your aunt’s. Just sayin’…

3. Plan your time
Fly on Tuesdays or Thursdays, or at impossible hours.

Who goes away on a Tuesday or Thursday, right? You, that’s who. Otherwise, you have this:

  1. Mondays – business people leave on business trips
  2. Wednesdays – Long weekend trips usually start on Wednesday, but it’s still a pretty good option.
  3. Fridays – those business people from point 1 come back home from work
  4. Saturdays – people usually leave on vacation on Saturdays
  5. Sundays – people usually come back from vacation on Sundays

On the same note, if you can, take the red-eye. No one likes the red-eye. You don’t like it either, but you tend to hate it less when it’s almost free. Plus, some people might miss the flight because they couldn’t wake up/get ready/beat the traffic in time. Their failure = your success.

4. Choose destinations with more flights per day


Especially in the beginning, when you want to try things out. Something I truly recommend. This is how we got to see Stockholm, and we ended up loving it.

Don’t go to the Maldives on your first trip. You probably have one or two flights per WEEK.

If you miss it, you’re screwed. Half of your vacation is gone, and flying 12 hours to stay there for 3 days is useless.

Choose these destinations only if you have benefits on many airlines and you can leverage them out neatly, getting you to miss at most 10-12 hours.

5. Choose obscure destinations

Or maybe only the entry point. For your Japan trip for example, you can choose Nagoya over Tokyo or Osaka. Not so many people go there, and you will probably move around the country anyway.

And, who knows, you might discover some pretty cool places and enjoy them in a less crowded fashion.

6. Geography is your friend

Learn all the big hubs on every continent, especially the ones where the best airlines go. Also, keep in mind that some hubs provide better connections for some destinations, and you should also know these.

When you’ll be unexpectedly denied boarding on the non-stop flight, you’ll immediately know what are your options, instead of running around in circles, panicking and sweating. You’ll also look smarter like you know what you’re doing.

7. Geometry is your friend

I can just imagine your mind blown by this one.

If there’s no direct flight available with your airline, choose to take a star-shaped approach: go with your company in a hub as close as possible to your target destination, and from there take a short flight (probably there are more per day), either standby or a usual ticket.

You’ll get to leverage your priority, maybe even score a Business class for the long leg, which may not be an option in other cases.

If you want to go from New York to Paris, and your company takes you to Frankfurt, use this option. The long flight is probably once per day, but from Frankfurt, you can get to Paris using so many options, some of them are low cost, some other may be trains or other means of transportation.

8. What if…?

Plan and have ready all of your options for all the “What if?”s that may happen. If decision charts are your thing, do one for every trip. Potential things to put on the list can be, but are not limited to:

  1. You need to split the party between classes
  2. You are faced with a downgrade on a long haul
  3. You need to split across multiple flights, and some of the fliers are kids, so they cannot fly alone.

You need to discuss this with your fellow travelers. ALL of them need to know what to do in every case.

You need to answer right away when asked by the staff about your decisions. And you need to act on this decision right away since there’s probably no time to give tasks to people at that point.

Your best bet? Probably you should remain the last to get on the flight, so you can handle everything. You can rarely do stuff while flying, so you have to take care of everyone before take-off. No pressure…

9. Research all possible routes

And order them by priority. And I mean ALL possible routes. Look at our plan when we were getting ready to go to Japan:

Trello board with all options we had for our trip to Japan
These were all of our options to get to and out of Japan

You may only have a few minutes to get to your next best option, and you don’t want to miss a potential lead while you’re busy looking for it.

Also don’t forget the time you would need if you have to get out and take your checked luggage, and maybe check it in again. That’s why I have decided to put the rule 1 where it is.

10. Buy firm booked (confirmed)

If you have to be somewhere. Also, buy it for one day earlier than needed. In case of being offloaded, you’ll get to the destination in 24 hours anyway.

It’s pricier, but it’s still nowhere near the market price, and you get less risk and more peace of mind. You have to choose your battles at some point, and you need to know where that point is.

How to be prepared when traveling standby?

11. Free cancellation

Everything you reserve should have this mark on it. Accommodation, tours, on line bought entries to landmarks, visas with an expiration date – you name it.

All of these should have either a free cancellation policy in place or a loose interval in which you can use them. Sometimes even a day’s buffer may be of help. Or even a free cancellation until the day right before the trip.

12. Book like a pro

For your accommodation, make 2 reservations:

  1. one for the big vacation, let’s say a week.
  2. one for the first night, at the same hotel.

If you don’t get there, you lose the money for your first night, not for the whole reservation. The big one you can cancel if you’re not getting there at all because you have already applied tip #11.

Another option you have is to reserve the first night at the gate when you know you’re going to fly. The previous reservation should be made in advance though, because you may not find rooms available last minute.

13. Be organized

All the research that you do, keep it where it’s easy to access. A favorites file is always a good idea, but you can work with a notes file, a bookmarks folder, or even a printed version of everything.

My personal favorite for this is Trello, and I’ll explain why in a future post. Yeah, I must be fun at parties…

14. Prepare for the worse

Always be prepared if needed to spend your night in a hub, on your way to Indonesia (random choice, of course). You have to research hotels and things to do, you need to have all your basics with you and you need to know this may happen at any time.

Also, you need to have money to pay for any unexpected expenses that will appear. Deduct this amount from the bucket you’re saving by flying standby, and you’ll feel less stressed.

15. Always be prepared to pay your ticket in full

If you’re not getting on a flight for a few days, you might bite the bullet and pay in full. You cannot just lay around and wait for someone to miss their flight.

With the overbooking being more and more the norm across the aviation world, you might get old waiting for a seat for you.

16. Always have snacks, basic toiletries, and entertainment with you

If a layover is longer than needed, you will want to take a short “shower” in a toilet in the airport, so you don’t stink when you finally get on the flight. Or even worse, get bumped out because of it.

If there’s no more food on board, you will be grateful for the bag of chips you bought yesterday at 20% of their price from the airport.

If the entertainment system is broken on one of the seats on that flight, you bet that’s going to be your seat. You’ll be happy you took my advice and you have your reMarkable full of books, or your tablet or laptop full of movies. They are good on long layovers as well. And reading is generally good for you.

Final thoughts

Phew, that was a long one. And I am SO sure I’m going to add more to it over time, once I get new ideas or learn new tricks. In the end, as long as it helps people, I would be delighted to make this guide better and better.

For now, this is the second part of this series. I hope you enjoyed it. I loved writing it and I was thinking of doing so since I started enjoying my staff travel benefits. I loved planning trips anyway, I always love a bargain, so this is like a paradise to me.

Let me know in the comments if you find it useful. And don’t forget to read the other episodes of this series:

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