Richard Kerr

A simple internet search for cheap airfare led Richard to chasing the proverbial white rabbit down the hole towards points and miles. Richard’s passion is exploring the inner workings of loyalty programs in order to provide readers the best strategies for maximizing their loyalty account balances. Richard has traveled to over 40 countries and has lived in the UK and Japan. His wife, Emily, and son, Thomas, are his favorite travel companions. Thomas has visited six countries and taken over 20 flights at the ripe old age of one. Richard graduated The Georgia College in 2007 with a BBA in International Business followed by Naval Officer Candidate School in Newport, RI where he was commissioned an Ensign in the U.S. Navy Supply Corps. He served as the Supply Officer of the ballistic missile submarine USS Kentucky (SSBN 737) from 2010-2013 followed by a three year your in Japan as a Material Control Officer responsible for supporting maintenance on Navy and Marine Corps aircraft outside of the US. Richard is currently a lieutenant working in the Washington D.C. area inside the Navy aviation community. Contact Richard via email at or keep up with him on Twitter and Instagram (@thepointsjock). “Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one's lifetime.” – Mark Twain

Stress, Puke, Fatigue and Traveling Babies

I recently returned to the East Coast from a family jaunt to the deserts and red rocks of Arizona and was reminded that plastering social media with great landscapes, fancy resorts, and frolicking babies is easy. The stress, puke, and fatigue that come along with traveling babies is not. Allow me to recap the hardships we faced on our trip and share the lessons learned. Plane Travel We flew Southwest Airlines non-stop from Baltimore-Washington International to Phoenix on a round trip itinerary utilizing my Southwest Companion Pass. It’s a great deal because it means I only had to buy...

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The Merits of International Family Travel

This post was sponsored by The Jordan Tourism Board of North America. Opinions were not directed by the sponsor and are, as always, my own. Every parent in the world wants the best for their children — but how do we know what’s best? How do we know our American views are best? My son was born just outside of Tokyo two years ago. The only regret I find myself with now that we are back in the states is that he wasn’t older during his time overseas. With our daughter having recently joined my son in the family, I am reinvigorated...

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The Secrets to Fly Cheap or Free On Peak Travel Dates

Knowing how to fly cheap or even free on weekends and holidays is crucial to protecting your wallet and reserving the few precious days off American workers receive. The problem of course: that is when everyone wants to travel. Finding cheap plane tickets and or even being able to find saver award space when using airline miles is nearly impossible. Add a wife and kids in tow, and you could easily say goodbye to any vacation slush fund you’ve managed to save up. Today, I’ll share my strategies on how I fly my family of four for cheap, or...

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How to Use Points for Travel: August 1 #TDAD Twitter Party

Traveling Dad is all about finding discounted or free travel and one of the easiest ways to routinely travel at a bargain is to rack up and (properly) use credit card, hotel, and airline points and miles. With that in mind, during an August 1 Twitter Party we’re corralling some points and miles experts and joining forces with our friends at Traveling Mom to give you the lowdown on how to get free hotel nights and flights for your family. Whether you’re just getting started in the points and miles game or already consider yourself a points aficionado, we bet there’s some...

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I Flew 8 Flights and 14,000 Miles for Fun Last Weekend

If you travel often like I do, airline elite status can be a great thing. Free upgrades, bonus miles, less lines to stand in and priority boarding to grab much desired overhead bin space can all make a trip much smoother. Over the long 4th of July weekend, I took an eight flight, 14,000 mile journey purely for the sake of collecting airline miles to achieve American Airlines top tier Executive Platinum status. Today, I’ll recap my recent eight segment mileage run to Panama City, Panama and explain the benefits of American Executive Platinum status. Earning Status Back in May, my...

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Traveling Dad Hosts 100 Points and Miles Enthusiasts in Washington DC

Nearly 100 loyalty points and miles enthusiasts gathered recently at The American Tap Room in Clarendon just west of Washington DC for an evening of networking and discussion on the latest tips and strategies to utilize credit card, airline, and hotel points and miles. Members of the Travel Hacking 101 Facebook Group came together for the second in a series of regional meet ups offering group members a chance to ditch the computer and meet in person. Traveling Dad hosted the evening in order to boost awareness about the ability of families to travel for steep discounts utilizing loyalty programs....

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When a Travel Pro Fails Miserably

There are certainly more travel savvy folks than I, but I do like to consider myself on the very experienced side of the spectrum. I’ve lived on three continents, visited close to 40 countries, and faced about every situation possible when it comes to the logistics of getting from point A to B. Today, I’ll share how after even all of that travel, there are times when I fail miserably. The Late Show Last year I was visiting Kuala Lumpur, Malaysia for business and was very proud I had located and booked the Le Meridien hotel which sits directly...

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How to Drive Long Distances With A 1-Year-Old

This past February my wife and I moved back to the States from Japan. Our new home would be in the Washington, D.C. area, but we first needed to make the family rounds through Georgia. We had arranged to buy a car in the South. Thus, a long distance road trip from Georgia to D.C. with our toddler was staring us in the face. Here’s what I learned on that trip. Entertain Your Kid This really starts long before you get in the car. By the time you begin packing for the drive, make sure you have the things you know...

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How to Survive a Long Flight with a Baby

My wife and I had the great fortune of living in Japan from 2013-2016, and the even greater fortune to have a (surprise!) baby boy born there in 2014. While my greatest concern was to have a happy and healthy family, because we lived in Japan, the thought of long haul flights back home with a baby crept constantly into the back of my mind. Through trial and error, sometimes disastrous error, we have figured out how to prepare for and successfully execute long haul flights with our son. Today, I’ll share my top tips and tricks you can...

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Top 5 Family Credit Cards to Earn Free Travel

It’s difficult to go through the day without being bombarded by more advertisements than we ever thought possible. And when it comes to the credit card world, these advertisements all seem to promise us something for nothing. While I do believe in the age old economics adage “There’s no such thing as a free lunch,” there are credit cards that have provided my family with tremendous rewards. These rewards have allowed us to travel the world, twice in first class, for almost free. Here now, my current top five credit cards that might help your family earn free travel. Chase Sapphire Preferred...

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