How to Travel the Right Way

You travel the wrong way.

If you are overwhelmed by this scene you probably don’t spend your life in the air. Don’t worry I’ll teach you how to travel like a pro even if you do it once a year. This will be a two-part post to give you time to digest it.

For my work I typically travel 30+ weeks a year, mostly domestic flights and unless I can help it I fly Southwest or United, stay at Hilton branded hotels, and use Avis for car rentals. I just thought I’d list my bias preference upfront.

Why am I that picky? Because for all the troubles that you encounter when traveling away from home you need to have something to gain from it. Points/Status. These points have made traveling with my family practically free. I’m able to book hotel rooms for family, take spontaneous vacations (as much as possible with a house full of kids) all practically for free.

Here is what my travel has looked like for the past 4 years. Nothing super crazy, but well above the 1055 miles the average American flies each year.

I’ll break this article up into two parts, how to travel smart, and how to benefit from your travels. Traveling Smart will benefit everyone who ventures out on vacation or business travel. How to benefit from your travels will help you if you travel at least once every 18 months.

Traveling Smart

Apps and accessories

Before I get into each category below I want to stress how important it is to download the app of each provider you purchase from. You can at the very least manage your transaction, get status updates on your travel and in general have all of your information right at your fingertips.

In addition to the individual airline/hotel/rental car apps here are some of the travel apps I use that make my life a bit easier:

App in the air

Flight Radar 24

Android Auto/Apple CarPlay

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Wireless bluetooth noise canceling headphones – If you don’t have a good pair, and you travel often this is the single best investment you can make. I didn’t know I needed this until my wife purchased one for me a couple of years ago for christmas. If you are a baller and can afford the top of the line Bose noise canceling headphones, then have at it. I had a very nice pair of JBL headphones until I left them in a rental car. Now I have a pair of Plantronics headphones that were under 200 bucks.


Where to book

I am a big fan of booking on the airline website, you can normally get the best deals directly from the airline and don’t have to worry about any extra fees. The airlines are also normally more upfront about seating assignments as well. One critical fault the individual airline websites have is the inability to search each other’s sites for flights. For that reason I like to use aggregating websites initially to look up flights. My favorite is or you can use or They are all pretty similar so it’s just a matter of preference. After I find my flight, I return to the airline website and purchase my ticket.


This is a very overlooked travel item. I have traveled with duffel bags and suitcases before and I not have seen the light. I highly suggest a well made roller suitcase like this, or this, or this. It all depend on how often you travel, I purchased an inexpensive roller suitcase from costco for about $50 that lasted about 30 trips before the wheels gave out. Since then I’ve learned the error of my ways and purchased a Travelpro roll around and backpack.

Most of my travel is less than 5 days and is for business, so I use a carry-on size roller bag with a backpack. I absolutely abhor checking luggage, waiting in line at the counter to check it in, waiting a baggage claim to pick it up, not to mention luggage lost by the carrier or being stolen. My roller bag fits the approved carry-on size for US domestic airlines of 9 x 14 x 22 including handles and wheels (list of airline carry-on luggage sizes here). I pack all my clothes, toiletries cables and a spare computer monitor in my carry-on. My laptop, tablet and work supplies in my backpack. It works out very well. Bottom line is save your time and possibly money, if possible try to carry on your luggage and don’t check bags.


Pack with a purpose. I’m serious. You aren’t traveling with your closet. You don’t need fifteen options on your 3 days away from home. Pick your clothes each day and set them aside. For your casual outfits, lay the day’s clothes, including underwear and socks, on top of each other and roll them up. Then you will have one roll per day. It already matches, you already put some thought into what it is, and you are done. You will also not throw in extra items. For any business wear, I suggest wearing it during your travel. Who would you rather sit next to on the plane, This guy? Or this guy?

Personally, when I want to wear a suit for business, I wear it for my travel or I pack it in a good suit carrying case like this one.  Suit roll case.

Last note, Please for the love of god check the TSA website for what you can and can’t have in your carry-on and checked luggage. I check it every couple of months here.

Airport Arrival and parking

How are you getting to the airport? Driving and parking your car? Having family/friend/Uber drop you off? Do some homework ahead of time. If you are parking your car you have to figure out your budget. Some of the closest parking at airports can be $30-$75 a day. Figure it out ahead of time, many parking garages provide free shuttles and discount rates when you book ahead of time. Take into account the time to find a parking spot and get to the terminal, which can vary wildly from airport to airport. When being dropped off, consider, at the very least buying a good cup of coffee for the wonderful person dropping you off.

When you arrive, check in at a kiosk (unless you checked in on your phone) and proceed to the correct TSA security line for the terminal.


Everyone dreads the Transportation Security Agency lines. But let me tell you, the problem with the lines are the people in the lines. It seems everyone in the line has never been to the airport before. If you didn’t listen to me earlier and have a bunch of crap you shouldn’t have in your luggage, you’re not going to have a good time. They will make you take it out, go through your bags, whatever. Also you are going through at least a metal detector, or a naked body scanner, or a grope down from a TSA agent. Take off all your metal, your cell phone, your wallet, etc and put it in your bag WHILE you are standing in the TSA line. Dude, seriously you have time, use it wisely.


If you travel at least once a year, go fork out the 85 bucks or whatever they charge and sign up for TSA Precheck. It’s worth it. You don’t have to take off your shoes, belt, or light jacket. You also can leave your electronics in your bag. Talk about saving some time. The other huge benefit is you only have to go through a metal detector not the naked body scanner. I like to look people in the eye who get to see me naked, call me old fashioned.

Normal lines

The opposite of precheck, longer slower lines full of people who travel once a decade. “Oh, I need to take off both my shoes?” “But why can’t I take this bottle of water through here?” The way I see it, if you want to practice patience and like spending extra time at the airport, then go through the regular lines.

In Part 2 of this series, I cover the airlines, hotels and rental cars. I also discuss the different points programs, what’s good, what’s not and what to look for.

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Matt is a husband, a father, an avid motorcycle rider, and an all around awesome guy.

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