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Travel Tips from a Touring Artist

This post was originally published on my personal blog in April, 2014. I've added a few notes where my thoughts or opinions have changed since then, but most I still agree with most of what I wrote.

Welcome to the Life of a Touring Artist

In late 2010, I quit my job and started working as a touring artist and educator full-time. Since then, I’ve gone on dozens of flights, a handful of road trips, stayed in hotels, university guest housing, and on people’s couches, spent way too much money on shitty airport food and side-of-the-road diners, and met tons of students and teachers and fellow artists and activists and educators. In the course of all that, I’ve learned a few lessons about making travel as easy and pleasant (or, at least, as un-un-pleasant) as possible.

Frequent Flyer? You need TSA Pre

A person rolling a suitcase at an airport

My first big piece of advice for anyone who flies more than a few times a year is to enroll in TSA Pre. This program allows frequent travels to (willingly) undergo an extra one-time background check and get a ‘known traveler number.’ If you look at booking websites the next time you fly, this known traveler number can be entered when you buy a ticket (usually near the frequent flier info) and flags you in the system as eligible for pre-check. Which means, what, exactly?

Well, first, it means you get to go through MUCH shorter lines at airport security. Look for the TSA Pre signs next time you fly. I’ve rarely taken more than 5 minutes to get through the line at Midway or O’Hare, perhaps a quarter as much time as it usually takes. In addition, you don’t have to take your shoes off, you don’t have to take your laptop or liquids out, you can leave on your jacket, and you go through a metal detector instead of the fancy new scanners. All much faster.

The downsides are partially financial and partially ideological. On the financial end, my Global Entry card cost $100 with a four year expiration date. TSA Pre is $85. (Wait, Global Entry? I thought this was TSA Pre! I’ll take about the difference between Global Entry and TSA Pre in a minute.) You also have to go to a nearby airport – O’Hare for me – or processing office for an interview with an agent and to have your fingerprints taken. Which brings me to the next downside: ideology.

By enrolling in TSA Pre you are implicitly supporting the work the TSA does, subjecting yourself to an additional background check, and willingly putting yourself in ‘the system.’ On the one hand, I think this is bullshit. On the other hand, it’s really really really really nice. For me, and the amount I travel, I’m willing to hold my tongue and make a deal with the devil.

TSA Pre versus Global Entry

A security camera
Yeah, you're probably being watched

To get access to the TSA Pre line at the airport, you need a known traveler number. The simplest way to do so is enroll in the TSA Pre program. Except TSA Pre had said ‘coming soon’ on their website for months and months, so I got impatient and enrolled in Global Entry. This program also provides enrollees with a known traveler number (and thus access to the TSA Pre lane) but also makes traveling to and from participating countries a little faster. For example, I’m writing this paragraph in the Toronto airport. Instead of going through the longer custom lines, I was able to use an automated kiosk to scan my passport and my fingerprints. The kiosk then printed out my customs entry form and I was on my way.

To be honest, if TSA Pre had been accepting applicants six months ago, I probably would have just applied to it instead of Global Entry. My current stay in Toronto is the first time I’ve traveled internationally in years, and I wouldn’t be surprised if it’s another few years before I do so again. So if you fly a ton in the US, I’d highly recommend TSA Pre. If you want the TSA Pre convenience but also the ability to move quicker through customs when traveling internationally, go with Global Entry. (As a side note, the Global Entry website seems much less user-friendly. You have been warned.)

A Final Note on TSA Pre

If you book a flight with a known traveler number, you can see if you’re selected for TSA Pre on the boarding pass: It’ll say PRE CHECK. But having a known traveler number doesn’t guarantee pre-check, it just gives you a (high) chance of getting it. In the half-dozen flights I’ve flown since getting my known traveler number, I’ve gotten pre-checked every time. Woot! But to keep the system at least semi-random, apparently getting a known traveler number only gives you a (high) chance; the woman who interviewed me at O’Hare said she’d anecdotally heard travelers were getting pre-checked 8 or 9 out of 10 trips. That’s totally worth it to me, but I don’t want to mislead anyone that this will guarantee a quicker trip through security every single time.

Note from April, 2019: I still encourage frequent travelers to enroll in TSA Pre, as I can't think of a time when I didn't get to go through the faster Precheck line. Haven't used Global Entry, though, as almost all of my flights are entirely within the United States.

Frequent Flying – So Many Airlines to Choose From

The inside cabin of an airplane, with display screens on the back of passenger seats
I download videos to my tablet rather than rely on inflight entertainment

My next piece of advice for frequent fliers would be to pick an airline and – whenever possible – stick with it. Wrack up those frequent flyer miles (perhaps with a credit card), and get familiar with your airline’s seating policies, boarding process, their terminal at your home airport, etc.

I like Southwest. They’re generally at the bottom of the price range, if not the absolutely cheapest, which works for me. They also have a forgiving ticket change policy: you can always get your full travel fare refunded as a travel voucher, and you can get it back as cash if you paid for a higher ticket. I rarely do this, since I travel enough that travel vouchers are fine with me, but it’s good to know.

I also like Southwest’s open seating policy: they board in a specific order, but once your’e on the plane you can sit in any open seat. Paying for a more expensive ticket means you get to board first, but you can also pay a bit extra (I think $12.50 per ticket, so $25 for a round trip) to get into the first boarding group. It doesn’t guarantee the very first row, but I’m rarely further back than row four or five. I realize it may sound a little fru-fru to pay for that kind of luxury, but I think it’s worth it.

I also have a backup airline, in my case American Airlines. They fly just about anywhere Southwest doesn’t, and I like their service more than United. (I always feel like United is trying to advertise to me at every available possibility.) I have a frequent flyer account with AA, too, although my miles are (obviously) accruing much more slowly than on Southwest.

I do know some people who prefer a general travel credit card (I think this Capital One card, although I know there are others) where you can use points on any airline. I haven’t gone this route because I almost always fly Southwest anyway, so would rather earn extra points specifically for them, as opposed to fewer points usable anywhere. But if you don’t have a preference for a specific airline, this may be the way to go.

Note from April, 2019: I've become spoiled by assigned seating, so fly American more than Southwest these days. I've also switched to primarily using my Chase Sapphire Preferred credit card, as it is supposed to be one of the most versatile reward/points cards out there.

Luggage and Packing

Old-looking suitcases stacked neatly in shelves.
Honestly, just figure out what kind of luggage works for you, and do that.

When I started touring, I used my standard roller luggage and the backpack I’ve had since college. It worked well enough, but the more I traveled the more frustrating it became. I’d notice how obnoxious finding clothing was, or how difficult it was to keep track of charging cables. Which led me to a major rethink of how I pack and what luggage I bring.

A lot of my thinking comes from the website OneBag, which advocates a single, non-wheeled, soft-sided bag. Their argument – that you should ditch roller suitcases in favor of soft-sided bags – is based primarily on weight and flexibility, which makes sense to me. Unfortunately, the amount of shit I need to bring – books to sell, changes of clothing, hair dryer, a different pair of shoes, and on and on – means traveling with just one bag is impractical for me on all but the shortest of trips.  But what I have started doing is checking my roller luggage (which is free on Southwest!) and bringing a single, soft-sided bag as my carry-on. Specifically, I bought the Tom Bihn Tri-Star, which I love.

It functions in a bunch of ways, including a shoulder bag and a backpack, which makes it super flexible. It’s also designed first and foremost as luggage, which means it can carry a change of clothing (say, for an afternoon workshop and an evening performance) without anything getting wrinkled. That’d be difficult with most traditional backpacks. It also has tons of little pockets and compartments, and it’s just super well made. The fact that it’s all fabric and flexible means I’ve fit it into overhead compartments that never would have accommodated my roller suitcase.

Tom Bihn is definitely on the upper end of the price range, but I highly recommend them (or any other company doing high-end work) because I use my bag a lot and want it to last. I also like the Tri-Star because it doesn’t look like a straight up backpack or suitcase, so I feel a little more professional bringing it into workshops or student meetings. It appears I’m not living out of my suitcase quite to the extent I actually am. I also really like the backpack function of the Tri-Star, as it makes navigating terminals a lot easier. Yes, it takes more energy than rolling a suitcase, but I have both of my hands free.

My next luggage purchase may be to replace my current roller suitcase – a pretty standard, two wheel affair – with a hard-side four wheeled setup. But I’m trying to hold off until my current suitcase actually starts to die. I needed something like the Tri-Star (although I’m sure I could have lived with a cheaper backpack) but I don’t yet need a new suitcase.

Note from April, 2019: I've entirely gone back to roller suitcases because I'm lazy and ended up not wanting to carry everything on my back. Using roller suitcases is also easier because Southwest doesn't have a fee for checked bags, and my American Airlines credit card allows one free checked bag per flight, even if you didn't book the ticket using that credit card! Specifically, these days I have this pocket-filled eBags backpack, and Wirecutter-recommended carry-on and checked-bags from Travelpro.

Packing Hints

Even if your luggage is fine, I also highly recommend zippered mesh packing containers for clothing and a dedicated clear container for liquids. The Tom Bihn ones fit specifically well with their line of bags, but you can find less expensive versions of both on Amazon. Being able to pack clothing in individual containers – as opposed to simply putting everything in the same giant suitcase – has made getting dressed out of a suitcase much easier for me, and feels like an upgrade to my old suitcase without spending a ton of money.

Other Travel Purchases

Two SCUBA divers floating above coral and fish
"Let's go exploring!"

A really great piece of advice I got when I started to tour was, “Buy a travel version of everything you know you need to pack every single time you tour.” This includes things like extra USB chargers and cables, travel toiletries (toothbrush, toothpaste, shampoo and conditioner, hair brush, etc). (I’ve linked to a couple of things I like.) Basically, you want to make it so you have to repack as little as possible; as much as possible is already packed. So while I still need to remember my actual phone, I don’t need to worry, “Did I pack my charger?”

Think through what to include on your own packing list; here are a few suggestions to get you started:

  • A travel blow dryer. Admittedly, most hotels will have a blow dryer, and folks who air dry can leave this off their list. But I’m currently sitting in a very nice university guest housing suite that doesn’t have one, so I’m glad I brought mine.

  • I’ve come to love my mini surge protector: it functions as a dual-USB charger and – when at airports – means I never have to worry about all the outlets being taken. I’ve already made some airport friends by giving us all room to charge our gadgets. The specific one I linked to is a little bulky, but I’ve found it worth the extra size/weight.

  • A cheapy car charger adapter, because I use sometimes drive rental cars to get to/from a campus, and use my phone as a GPS.

  • A folding travel tray. My aunt got me one a while back;  it was from a craft fair, so it’s not the specific version I linked to, but it’s the same basic idea. I was very skeptical at first, but have fallen in love. It provides an incredibly portable place to put earrings/watches/hair bands/etc before going to bed without worrying they’ll roll onto the floor or get forgotten when I pack to leave.

  • Someone gave me a pad of paper packing lists at some point. (Not that specific version, but you get the idea) I used one as a test, and really love it. It gives me a quick visual check of what I’ve packed already, and going through it provides a final reminder of what I might need that has – on occasion – saved my butt.

  • Candy! No, not for you (although YMMV) but to give to people. Specifically, I buy a bag of pre-wrapped candy (Rolos, Starburst, etc) to give to the first flight attendant I see when I board an airplane, saying, “These are for you and the flight crew.” At the very least, it makes them happy, which is generally worth it for me. Flight attendants don’t get a lot of love, so they’re almost always appreciative. This goes double for Southwest (which is a little less stodgy than other airlines) or small regional flights (where the attendants really have to work their ass off for little pay and even less appreciation). It also often gets me perks: free drinks or extra snacks, a suggestion to move to an empty row, and even (on one glorious flight) a bump up to an empty first class seat.

Some Final Thoughts

More broadly, give yourself as much leeway as you can when traveling. If at all possible, I try to avoid traveling on the same day I’m performing or conducting a workshop. This is both for my own energy and in case there’s a travel delay or cancelation. The exception for this is generally if I know it’s something I can do a little drained (like Trans 101) or if the travel is still in the Chicago area. My rule of thumb is that I try to get there a day before teaching/performing and leave a day after if I’ll be traveling more than ~3 hours each way, including to/from the airport or whatnot. I’ve definitely broken that rule on occasion, but it helps me map out travel plans.

A person with long hair and a backpack, facing away from the camera, with trees and mountains in the distance
"What are we waiting for?"

All of these purchasing choices and suggestions basically boil down to thinking about what’s gonna make things easiest on yourself when you travel. What do you not want to think about? The answer to that question will be different from person to person, and the financial value placed on the answer will be different. For me, not waiting as long in line on Southwest is definitely worth $25 per round-trip. It’s usually not worth $40-50, which is often what other airlines charge. But every so often – if I’m exhausted or know it’s going to be a long flight – I’ll splurge for a better seat or earlier boarding. Likewise, not having to think about packing chargers was an easy sell – they’re pretty cheap, and it makes for one less thing I need to think about.

So ask yourself what you’re always needing, or forgetting, or wishing you could do, to make your travel easier. Slowly but surely, travel will become easier. I promise. And let me know if you've discovered any amazing travel tips on your journeys!

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