How to Earn Points and Miles for Your Dream Vacation

Many people suggest the way to begin earning points is to have a destination in mind and research flight options and hotels for that destination. I don’t think that is the best way for a beginner because it can be too complicated. 

The Wrong Way For Beginners To Earn Points And Miles

Let’s pretend you want to go skiing in Breckenridge, Colorado for spring break. You then have to research which airlines go from your home airport, I will use DFW (Dallas/Fort Worth) to DEN (Denver) and the Flight Connections website (no subscription). 

It looks like I have 3 options: American Airlines, Frontier, United Airlines. At this point I consult the list of which credit cards offer miles AA, United and Frontier.  For this I use my Transfer Partner Cheat Sheet. (Subscribe to my newsletter and I will send you my Transfer Partners Cheat Sheet.)

At this point a beginner might thing their only option is United and might also be very confused about Frontier via Marriott.

Remember in previous posts I mentioned airline alliances.  Here is where they come into play.  May I introduce members of the One World Alliance.  

Notice anyone that you thought we should not bother with on our miles earning for spring break?  American Airlines is part of the One World Alliance and they release award space to their Alliance partners.  If you have points that can transfer to British Airways you can book award seats on AA flights. 

Similarly United Airlines is a member of the Star Alliance. 

Going back to the Transfer Partners Cheat Sheet we now have a ton of additional options.  This is what our options look like now. 

(The airlines in gray are still unfamiliar to me, I haven’t transferred points to those airlines or researched them so I typically eliminate them when I am doing research for my trips.)

Overwhelmed yet? I think I have made my case about this not being a good strategy for beginners so I will stop here.  This flight research scenario will continue in the points and miles 201 tutorial when I get around to writing it.

How To Earn Points For A Hotel

Let’s look at hotels for our Breckenridge spring break trip. The best place to start researching is MaxMyPoint.  We are given 7 results, 2 Hyatt, 2 Marriott, 3 Hilton. 

Combine these options with the flight options and you need to decide between earning Amex, Chase, Capital One or Citi Points. What should you do?

If you were not overwhelmed about the flights, I bet you are now! 

Because I want to beat this dead horse, let’s pretend you continued through this method of planning your hotel and you find that you need 100k points per night to stay 5 nights at the Hilton. You go about earning those 500k points and then six months later when you go to book for the next spring break, all of the rooms are sold out or the rates have changed and now you need 120k per night. You will have gone through the effort to earn the points for a specific Hilton and now you need to pivot.

This is not a good points and miles experience for beginners.

How I Started Earning Points and Miles

When I first started intentionally earning points, I got the credit card that everyone was raving about. I had a temporary higher than usual sign-up bonus and everyone on the internet made it sound like I had to get it now or else it would be gone forever. I was very wrong.  Sign-up bonuses come around frequently so don’t get caught up in any hype. 

Although I had no clue what I was going to do with those miles I knew that I wanted to vacation and save money.  Beach, city, mountain, I did not care. At that point all I wanted was a way to save money on vacations and figure out the rest later.

How You Should Start Earning Points and Miles

The approach I’m going to suggest for how you start earning points is to look at where you spend money and pick the card that offers the best multiplier for one of your largest segments of spending.

I might be going out on a limb here but I think the majority of the population eats food.  Whether you cook all meals at home, dine out every meal or a combo of both, we all buy food.  That is why I generally recommend the first points earning card is the Amex Gold Card.

I feel pretty strongly this is a card that will be in your wallet for the long haul. So strongly that I have an entire article dedicated to all of the reasons why the Amex gold card is a great first card so I won’t repeat all of the reasons here.

Thanks for reading, friends! Happy Travels!