Travel Deals Through The Generations

Happy Father’s Day to all of your fathers out there! My day has been wonderful so far and it is a great thing to be with both my father and my children.

Travel Deals Through the Generations

I thought today would be a good to reflect on what I have learned through the years from both my father and grandfather when it comes to travel deals.

You know how people say that a person gets this or that from his father or is just like his father in some way. When it comes to travel deals, I truly did get these things from my father and he from his father. 🙂


Obviously, my grandfather did not get travel deals with the points earned from credit cards or from travel. In fact, almost all of his travel took place for the USA in his role as a sergeant in the US Army. His travel deals typically came through the mail in the form of hotel offers and airline offers from signing up for various programs at casinos. My grandfather was a treasurer for a union and many of their meetings took place in casino locations. As a result, my grandfather would sign up for their frequent visitor programs and they would send him free tickets and hotel comps. He took advantage of a few of these. He would take the family on some of these trips, as well as the union trips. To this day, he continues to get free hotel nights at a casino each month for his (limited) playing at the casinos. No matter what he plays with, he still winds up getting more in return than he ends up losing. 🙂


My father took the travel deal hunting to a different level. Again, most of our early family travel did not involved miles and points but he did deal searching through paper sources (advertisements, calling and making reservation requests, etc). He picked up a couple of free trips through various things early on and we were able to enjoy some great hotels in nice locations through his dealings with hotel staff.

One particular example involved our trip back from North Carolina (mid-90s). We wanted to stop over in Washington DC for a couple of days. He began calling various hotels to find a good deal. He finally found a nice deal at the Washington Marriott at Metro Center. The deal he had was for $55 for the night (the regular rate was much higher than that). When we got there, he thanked the desk agent that booked the rate for him and made it a point to bring something to show his appreciation (some food/flowers). On the final day of our stay, we found our bill under the door with a handwritten note explaining that she had extended my dad a “special” rate – $30 a night!

That was just one of the very many hotel deals my dad has received over the decades. People always were amazed at the great rates he could get. He could call a hotel (cold) and get a rate that was 30% cheaper than the cheapest published rate (without using any type of discount code).

Once miles and points became more popular through credit cards and bonuses, he started to do it in a big way – long before I was old enough to get a credit card. I learned quite a lot from him with travel deals!


Then it has come to me. I have learned a lot from my dad that has allowed me to pick up some great deals as well. In addition, it has helped me to really get into the credit card game to learn how to do even more. It is always a great time when my dad and I get together. My dad would pull out his notepad and I would pull out my tablet and we would start comparing programs and points. These mini point sessions helped both of us quite a bit as we learned different things from each other. However, still to this day, most of what I have learned has come what I have picked up from my dad.

Most Important Travel Lesson

One of the most important travel lessons I have learned from my dad is not exclusive to travel. It was to always treat the person on the other end of the counter/phone with the same courtesy and respect that we would want ourselves. In addition, we would always speak with them as more than just a business contact. Instead, my dad would always be able to talk with these representatives like friends. My dad would call someone that he had met at an airline/hotel/travel agency months after to ask after a family member that faced surgery or some other important appointment. He didn’t do this to obtain a good deal but as a way to show his care and concern for another person. Thanks, Dad, I appreciate that lesson and all the others that I have learned from you!

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About the author


Charlie has been an avid traveler and runner for many years. He has run in marathons around the world for less than it would cost to travel to the next town - all as a result of collecting and using miles and points. Over the years, he has flown hundreds of thousands of miles and collected millions of miles and points.
Now he uses this experience and knowledge to help others through Running with Miles.