Travel Tips for the Vacation-Bound Geek

Last week I had the opportunity to take a much deserved vacation – I left the world I knew behind, and thanks to the fabulous folks at my girlfriend’s employer, I was treated to an all-expenses (mostly, anyway) paid cruise of the western Caribbean, with stops in Miami, Key West, and finally in Cozumel, Mexico. The journey was lovely, the cruise was fantastic, and the ports of call were all beautiful, warm, sunny, and relaxing.

The vacation itself was absolutely fablous, if you can’t tell, but if there’s anything about taking a vacation that’s stressful, it’s often the process leading up to your departure. Thankfully, this out of town trip is the latest in a series of excursions I’ve made recently, and thanks to a few simple rules the process was smooth, simple, and easy – in fact, even getting through the TSA checkpoints on the way in and out were easy once we got through the lines! I hear you now: “How is that possible? Did you get groped? How did you survive?!”

Calm down – the first thing you have to know is that with patience, you too will be able to proudly say that your travel experience wasn’t nearly as bad as you may have worried it will be. With a little more patience, a little knowledge, and some prep, you might even enjoy the experience. Here’s how.

  1. Buy It When You Get There

    There’s an saying among people who travel frequently (and even those that don’t) that goes like this: “When packing for a trip, lay out all of the clothes and all of the money you’ll need for the trip. Then pack half the clothes and twice the money.”

    The saying is definitely true, but for those of us who don’t have the budget to re-buy half of their wardrobe every time they fly out of town, or who would rather wear their own comfortable clothes than pay to launder or re-purchase their belongings when they’re away from home, there’s still some merit to taking a more measured approach to the phrase.

    For example – all of the TSA regulations around gels and liquids aboard aircraft are definitely a pain to work through, so why bother packing toiletries at all? If you’re flying (and I’m assuming you’re flying for this example – trains, buses, and your car don’t have ounce-limits on deodorant) just leave all of your toiletries at home instead of buying 3-ounce plastic bottles and trying to pour just a little shampoo from your big 18-ounce bottle to a small one.

    Let’s be clear: you’re probably headed somewhere that you’ll have access to a convenience store and can buy your toiletries when you get there. Or you’re headed to a hotel that has them available for you – every hotel has soap, every hotel has shampoo, every hotel has conditioner. Many, if not most, hotels have deodorant and other toiletries you can request at the check-in desk, or available to purchase at least.

    If you have a special need though, or you really like your brand of product, make sure you pack a little bit of it in your carry-on luggage or in a bag you don’t have to check on your flight or train or bus. This way you don’t have to run around to different stores to find the exact products you like or need, and you avoid getting to your destination stinky only to learn that the toiletries in your baggage has been lost, stolen, put on a different plane/bus/boat, etc.

    Toiletries are one thing, but what about other things? Gadgets? Clothes? Sure – they apply. Your hotel may not have a pair of shorts in your size, but it might make more sense to drop by a local department store and buy a pair to take with you to the beach than pay however much you would have to to check your bag. The same applies for some surprising gadgets – cell phone chargers, for example, are notorious for being available in all shapes and sizes in lost-and-found bins at hotel desks.

    Before you try and shove it in a bag or decide to check luggage, think about how much effort it would be to get on the other side when you get there. You might be better off buying when you arrive.

  2. Carry-On Only, If Possible

    With airlines charing more and more to check luggage (on our recent flight, American Airlines charged $25/bag – you didn’t even get the first one free, and they’re hardly the most egregious offenders – Delta charges by weight!) and other airlines like Southwest marketing themselves on the fact that your bags fly free (to a point,) there’s absolutely no reason to check luggage if you’re not carrying something specific, or you’re traveling for less than 5 days.

    I usually snag a nice big bag with a retractable handle and wheels – medium sized because I like to pack light, but I’ve seen people board flights with much larger rolly-bags and stuff them into the overhead compartments – for my clothes and toiletries, and then pack my laptop bag, a nice Timbuk2 bag with a padded laptop sleeve that’s big enough for my gadgetry, laptop, chargers, cables, and a book or two.

    You’re generally allowed two carry-on items: one bag and one “personal item,” under which a laptop bag, purse, or backpack is included. My rolling bag goes in the overhead, and my laptop bag, usually packed full of all the things I need to entertain myself on a long flight, slides under the seat in front of me.

    This way no one has to touch my clothes and toiletries unless they need to be manually searched (and since they have to go through the X-Ray at TSA checkpoints and I watch the process,) there’s no possibility of my gear getting lost, put on the wrong plane when I make a connection, or stolen, since it should be in my possession at all times. I always know what I have, and I always have it available and at hand, even on the plane.

    It really is an incredible sense of security knowing you always have everything you need for your trip. Every time I’ve flown or traveled recently, I’ve packed using the carry-on-only method, and sailed through TSA checkpoints, never paid baggage handling or checking fees, never had to wait at baggage claim for a carousel to bring my stuff to me, never had to deal with search stickers and tags on my luggage from customs. Try it, you won’t regret it!

  3. Just Say No to Packing Unitaskers

    Part of packing light and making sure you can carry-on if you can is minimizing the number of things you bring with you that serve one purpose. On the cruise I just returned from, there was one night where a formal, suited dinner was in order, so I packed a suit with a shirt I could wear at more than one semi-formal occasion, there was no getting around that, but then it came down to the issue of shoes.

    I wanted to pack sneakers, since they would be best for walking around and general lounging. I wanted to pack dress shoes because they would look best with the suit. I wanted to pack flip-flops or sandals for above-deck chatter and poolside relaxation. I wound up compromising and packing a pair of black leather slip-ons, which I rigorously polished the night before I left.

    They were shiny and sleek enough to wear with the suit even if they weren’t patent-leather, they were comfortable enough for walking off-ship, and they were casual enough to wear while reading on the deck. I figured if I really needed hiking shoes or sandals, I’d be able to get them in a port of call, but I was betting on not needing them, and I was right.

    I could have wound up checking a bag and packing three pairs of shoes, but I managed to pick one that got the job done all around. This is the geeky way to think: what one solution fixes all of my problems in the best way possible, even if it’s not perfect for any of them? That’s what I’m talking about – apply those skills you’ve picked up in math, science, or technology to those real-world social problems that plague you at every turn.

    The same idea works for other things too: looking to take something to entertain yourself with on the plane? Why pack your iPod Touch and your Nintendo DSi and your PSP and your iPad when you can just pack your cell phone and a battery pack to keep it juiced while you game? Or, if you must, pack your favorite of the others and your cell phone to preserve your phone’s battery while you game on the gadget of your choice.

    The important thing to think about when you pack things is “when will I have the opportunity to use this?” and if you can only come up with one answer, leave it and take something that will also fill the same need as well as another.

  4. Keep Your Gadgets In Your Carry-On

    This one may sound like common sense, but it piggy-backs off of the previous one: pack light, pack only thing things that have multiple uses, and make sure you leave room in one of your carry-ons for your gear. The last thing you want is your precious iPad rolling around the cargo bay of a 747 with someone’s entire wardrobe resting right on top of the display, you dig?

    Keep that stuff on you and with you at all times. Plus, if you’re on a long flight, you have the benefit of being able to use it while you’re traveling.

    Look, I know that if you’re a photographer and your life is in your cameras, you’ll probably want to put them all into a Pelican Case or something similar and check them with luggage – that’s okay because those cases are virtually indestructible. If you’re an orchestra musician and you play the cello or the French horn, you’ll definitely need to check that as luggage – too big for the overhead bin.

    However, if you’re a geek traveling for a week, there’s no reason to check your laptop because you think it’ll be “safer.” Trust me, it’s safer with you. There’s no reason to check your DSLR if you have a padded place to put it in your carry-on, and there’s no reason to blindly check your electronics. Those days are long over, and you’ll be happier on the other end of your trip when you find out your gear still works when you get to your destination.

  5. Read the Rules Before You Head to the Airport

    There’s no surefire way to being the classiest guy at the TSA checkpoint than to make sure you’re up to speed on what you can and can’t bring with you before you even get there, and what you should do when you arrive. Seriously – everyone else will be in awe when you pull up to the X-Ray machine, pick up exactly the number of baskets you need for your items before heading into the X-Ray area, and then speedily doing everything you know needs to be done without having to be asked or coached by a TSA official.

    I say it often – take the knowledge and apply it: read the TSA travel guidelines before you hit the airport, and make sure you read Amtrak’s travel rules before hitting the train station. Pull anything you don’t need or that’s against the rules from your luggage before you hit the lines. There’s nothing more embarrassing than standing in front of an X-Ray machine while being forced to unpack items found in your bags as they went through. Make sure you have a valid photo ID or passport to show when you get there, and make sure it’s easily accessible and you don’t have to dig through your bag to get it.

    My personal goal? To be able to get the entire process down to a few seconds. I walk up, put my rolling bag on the conveyor with the small flap that holds my toiletries – each in their 3-ounce bag and all of them inside a clear plastic 1-quart bag – open for easy viewing. Lift three bins, one for my jacket (if I have one,) belt, shoes, wallet, cell phone, and sunglasses. One for my laptop bag, top flap open for easy viewing. One for my laptop. Arrange items as quickly as possible and push through the X-Ray machine. If I’m really good, I’m done before the person in front of me.

    When I get my stuff out of the machine, shoes go on first, belt and jacket go over my shoulder. Wallet, phone, glasses go into my pockets or into my laptop bag along with my laptop. Rolly bag is zipped shut, and away from the checkpoint we go – at least over to the area just beyond where I’m not in the way of anyone behind me. There I can put my belt back on and make sure I look sharp before continuing to the gate.

    I take part of my routine – okay, a lot of it – from this Wired Article on how to Fly Through Airport Security. It might help you when you’re reviewing dos and don’ts when you get to the airport or train station, and help you breeze through security.

In all of the times I’ve traveled recently, both before and after some of the TSA’s most controversial policies, these tips have managed to get me though without issue. No full-body scans, no aggressive pat-downs, no having my bag unpacked in front of me and then left to me to pack up. In some ways, I know I’ve been lucky – the worst that’s ever happened to me is the one time a TSA agent wanted to use a chemical scanning wand on the inside of my laptop bag because it had so many pockets, but that’s about it.

The key, to be honest, is to be patient (remember, everyone else has somewhere to go too,) be early (give yourself plenty of time to get yourself packed before you leave, to get to your destination – whether it’s by plane, train, or automobile, and to get through whatever security, border crossings, or checkpoints you need to pass through,) be knowledgeable (review the rules and regulations for where you’re going and your method of travel before you leave,) and be prepared (make sure you’re packed appropriately for your trip – avoiding single-use items, keeping your gadgets nice and close, and you’re packed according to the rules for your method of travel.)

The weather’s getting nice and warm and many of you will be thinking of spring break, summer vacation, and just taking a little time away from the office to do something fun soon. Hopefully with these tips, you’ll get there quickly and without a fuss, have a great time, and your trip back won’t be a stressful experience.

images in this post courtesy of Seattle Post-Intelligencer Photographer Andy Rogers: JetBlue Airways Embraer E190 Aircraft, and CNN – Shooting Video at a TSA Checkpoint? Here’s What You Should Know.





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  4. […] you’ll want to pick a pair of shoes that works in multiple situations. You know what I’ve said about multi-tasking pieces of your wardrobe. That may not always be possible if you’re buying shoes for a very formal affair, but if […]

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