So, I hate packing. This is really an understatement. Something about it makes me feel so overwhelmed, it’s actually ridiculous. I can manage a $13 million dollar theater, but trying to fill 2 suitcases and a book bag makes my head swim and I feel a strong urge to drink. If only my Hogwarts letter hadn’t gotten lost in the mail all those years ago, I’d just be able to wave my wand and make my clothes select themselves and dance happily into my suitcase. Sigh.

The thing about packing though is that it’s actually an art. An art a lot of people fail at – and the airlines have realized this and charge accordingly. So if you’re headed somewhere for a long time, or you really do just try to pack the kitchen sink when you fly somewhere for the weekend, here’s an example of how I used to pack for 4-6 months, in a variety of climates, without EVER paying a single overweight baggage fee.

#1 Split clothes between what I absolutely have to bring and what I want to bring. This is my essentials pile:

For work I used to have to wear an all black uniform everyday, anytime I was in a public space (unless I was off duty and hanging out in a public area on a formal night, then I need to be in formal clothes). So I would pack 3 pairs of black slacks and 3 black polo shirts, a black belt, a HAL sweater (because backstage is always FREEZING), and a cardigan (for when the backstage is more like Maine in October instead of the subarctic). Also, a favorite item of mine, steel-toed boots… which are so not luggage weight friendly, therefore, I usually opt to fly wearing them.

If I’m starting out a contract in Alaska or somewhere cold, I would add a sweatshirt, a jacket, a hat, and a long sleeved t-shirt. I also packed 2 pairs of jeans, because most nights on the ship end up in the Officer’s Bar, a staff-only area where we can wear whatever we want and talk about how the passengers/other crew have driven us to drink (just kidding… sort of). It felt a lot to me like tag day used to at Catholic school. I threw in two pairs of gym shorts and t-shirts because they can double as PJs.

After Alaska, transitioning to the South Pacific or Caribbean, where it will be summer, means adding 2 pairs of shorts (one khaki, for work), 2 tank tops, a bathing suit, flip flops and sandals. I would’ve also packed 2 formal dresses, 1 semi-formal dress, 1 pair of tights, 1 pair of leggings and 1 pair of high heels. A bunch of toiletries (which I actually could’ve bought most of them once I was at work if I wanted to travel with trial sized bottles – especially in Alaska because there’s easy access to Walmart in most of the ports) and enough underwear to last just over a week, because I’m lazy and sometimes my schedule was insane and I didn’t have time to do laundry.

Rule of thumb – all clothes should have more than one function. T-shirts you can wear to the gym and sleep in. Shorts you can wear to the gym and exploring in port. Ok, clearly the rule doesn’t 100% work because you can’t really multitask a formal dress, but the closer you stick to the rule, the better off you’ll be.

After sorting through what’s essential, I made a pile of what I would like to bring if there’s room:

My non-essential pile is usually a few extra shirts (because 4-6 months of rotating through the same 4 shirts eventually makes me snap and HATE them passionately, and then shopping gets involved and then that’s a problem packing to come home and overall, it’s just better to have packed enough clothing variety in the first place) and entertainment related items – books, my Wii, a Halloween costume, a Keurig, an extra pair of high heels.

#2 Pack Up the Essentials. Jeans and shoes are apt to be your heaviest items. I try to cram the heaviest items into the tiniest bag first, because if you cram your large suitcase with the heavy items, it’s going to be overweight, but if you cram the smaller suitcase full of them, you’re likely to make it under the weight limit (which varies from airline to airline, but I’ve usually found it’s about 50 lbs. a bag).

Suitcases have these inconvenient bumps at the bottom of them, which if you just start laying clothes over them, wastes space, so I try to cram socks and underwear actually in that gap, and you can pair two or three pairs of underwear together and roll them so they take up even less space. After that layer, I’ll usually put my dresses in their garment bag, because I can lay is across, pack on top of it and fold the top part of the garment bag over everything before I close the suitcase.

I knew of my non-essentials, my Keurig was the thing I most wanted to take from that pile, so it got put in early, in my littler bag, because when you’ve got something solid like that, you want to pack softer items like clothing next to it to optimize the space. I also ALWAYS put anything liquid in a plastic bag. Every single time I’ve traveled, something bursts, but it never matters, because it’s always in the plastic bag and I can just rinse that bottle and whatever other bottles I stored in the bag with it off and I’m good to go.

Another item to maximize is your carry-on. When I travel I also bring my purse which holds my wallet, passport, a book and my computer, and that’s what I keep easily accessible, but I always utilize the carry-on option too and try to pack my heaviest things that aren’t liquid (because, honestly, all those bottles of shampoo and hair junk are probably the heaviest things in my bags) in the carry-on, because as long as you don’t appear to be crazily struggling with it, no one is going to care how heavy your backpack is.

This particular time, I did better than usual. I wound up bringing a spare pair of sneakers because by the time I packed up my last suitcase, I was so far under the max weight (13 pounds), that I felt comfortable putting my steel-toed boots in. Everything from my essentials and non-essentials pile made it into my bags, other than my Wii. Sorry, MarioKart. I survived without you just fine.

Some Items to Think About Bringing If You’re Going to Live on a Cruise Ship:

Hand Soap – I don’t know about other lines, but HAL does not provide it for you in your cabin.

A Water Filterer – Bottled water is about $1.00 a bottle, which really isn’t bad, but you can buy a pitcher and a filter for about $20 and then refill filters every 3 months for about $10 and you’re likely to come out way ahead if you drink a lot of water.

A Keurig – Ok, so this is technically contraband on most ships. You’re not really supposed to have things like hot pots or coffee brewers in your room… but just pay attention to when cabin inspection is and put it in your closet that day. I love my Keurig. I like to drink a lot of tea, but I’m also very lazy and don’t like to walk all the way to the crew mess or Lido area for a cup of hot water – especially right after getting up. Now I don’t even have to leave my room. It’s fantastic and I love it.

Hard Drives – TV shows on hard drives are like currency on a cruise ship. If you join in June and you’ve got the latest season that everyone onboard has just missed, you will make lots of new friends immediately. Even if you just join at any time, people are happy to trade TV shows. You’ll find cruising is not nearly as exciting as most people who don’t work in the industry think it is, and we spend a lot of time trapped on the ship, in our rooms, with nothing to do. New TV shows are amazing.

Laundry Detergent – Because if you work there, you wash your own clothes. However, if you’re in an American based turn around port, it’s easy enough to get to a store to buy some, because laundry detergent is heavy (back to those packing skills).

A Laundry Basket – For transporting said laundry.

A Bottle of Water – Easily accessible for the day you join the ship. I feel like a camel once I’ve dragged all my bags onto the ship, and then all over the ship, and then into whatever dank, dungeon of a room they’ve given me to live in until handover is done and the current crew member in my position leaves. And you can’t go to the public areas to eat until you are in your uniform, so having a bottle of water to chug in one of my suitcases is one of the best tricks I’ve learned yet.

What money saving tips for flying do you guys have?