On top of packing well, you'll need to consider what you don't need. This is an obvious step, but figure out what's easy to leave behind based on where you're going. If you're heading to a friend's house or hotel with a guest laundry facility, you don't need as many clothes. You can also find a laundromat nearby and pay to wash clothing once. Obviously this is not the most fun thing to do on vacation, but you could even pay for the hotel to take care of it if you wanted. Check prices and compare them to the cost of your checked bags, because checking a bag (or two) on a round-trip flight could easily cost you more than a load of laundry.
In general, if you're trying to pack an item you're not supposed to take on the plane you should just not take it on the plane. There are times, however, where there are legitimate exceptions. For example, I once built a steadicam out of plumbing parts. While I'm not sure what this looked like to the TSA official checking my bag, I can imagine it looked like I was either planning on doing a little weightlifting on the plane or attacking the pilot with a series of lead pipes. I learned that day that the key to packing questionable items in your carry-on luggage is making them look a lot less questionable. In the case of the steadicam, the solution was to paint it and make it look like a professional product. It still caused confusion on the ride home, but since it didn't look like a plumber's torture kit I made it through just fine. Now we could talk about how a friend of mine snuck a broadsword on a plane, but that's the sort of thing you really just ought to ship via FedEx.
If a flight attendant tells you the overhead bins are full and you'll have to check your bags at the end of the gate, they generally don't know this is surely the case. Because they don't want to end up with a ton of passengers on board with checked bags they can't accommodate, they take preemptive measures and just start checking bags in advance. The easiest way to get around this problem is to get your bag check tag and do one of two things. First, you can do the nice thing, wait until you get to the plane door, and ask the flight attendant designated to great you if they'd mind if you tried to see if there's still any room left on the plane. If there isn't any by the time you're at the door, they'll know and tell you for certain. If there is, your politeness will often be rewarded with the opportunity to find out. You might also want to mention that you think it'll fit under the seat if that is a possibility. Whatever you do, just don't offer an excuse for why you need to bring your bag on the plane. The flight attendant is going to already be in denial mode because s/he's been dealing with frustrated passengers. You're in the midst of a negotiation and providing a reason will give the him/her something to counteract. Normally , but your flight attendant will be prepared for a negotiation and you .
Got any other ways to avoid checking your bags (or dealing with those few times when you just can't get around it)? Share your strategies in the comments.
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