Getting Started in Travel Hacking

Getting Back into Travel

Now that the world is beginning to open back up again, the itch to travel is surely coming back to those who missed out for the past two years. As bad as we all want to go out and explore the world again, we also want to do it without breaking the bank, so that we can continue to go all-in on our coin accumulation and side hustles. This is where travel hacking enters the chat.

The art of travel hacking is where you take advantage of big sign-up bonuses over by banks for getting approved for their card and meeting various spending criteria over the course of a few months. When successful, you receive a reward that when used correctly, can get you thousands of dollars worth of value. This is how we travel for free on the banks’ dime.

So why doesn’t everyone do this you may be asking? The answer is simple, not everyone can be trusted with credit cards. The reason banks are so willing to give out these large bonuses is because they intend to make their money back on late payments and interest on balances from those signing up for these cards. Most people are fine carrying a balance, paying their fees, and letting the banks get exactly what they want.

This is why you should not travel hack if you plan on spending money you weren’t already planning on spending or do not have the ability to clear your balance at the end of each month. The purpose is to use these bonuses to earn free travel based on your current spending, not to stretch yourself beyond your means. But as long as you keep that in mind, the possibilities are endless.

With that, let me take you through which cards to grab and where to redeem them in order to make the most of your travel.

Part I: The Cards

This is the part people seem to struggle with the most. They see every card as equal and just apply for any airline or hotel card they see thinking it is a good deal. That is the wrong way to think of it.

All points are not created equal. Points that belong to a specific airline or hotel program by nature are not flexible. You cannot transfer Marriott points to Hilton or move Delta miles to United. By applying for one of these cards, you are immediately trapping yourself in a box on where you can redeem. 

How do we get around this? We focus on transferable points. Cards with Chase or American Express that are not tied to a specifically branded card can be used in drastically more ways than brand specific ones. For example, Chase Rewards points can be used with British Airways, United, Emirates, Southwest, and many others. By having a bulk of your points in flexible rewards, it gives you way more options when it comes time to book.

So then, which cards should you redeem in order to get the best deals? I am going to use a 12 month strategy, as I find this is the easiest way for people to pick up cards within their normal spending. If you have higher monthly expenses and can afford to open cards a bit closer together, go for it. But I will use 12 months for my example.

Month 1

Card 1 - Chase Sapphire Preferred

Current Bonus: 80,000 points + $50 grocery credit after spending $4000 in 3 months 

Round-up: The current bonus on this card is the best it has ever been. Typically it sits at 60,000 points, which is still a very good deal. This is the standard starter card to get introduced into the points game. You get a large number of points to start that are flexible and opens you to the following travel partners: Aer Lingus, Air Canada, British Airways, Emirates, Air France/KLM, Iberia, Jet Blue, Singapore, Southwest, United, Virgin Atlantic, Marriott, and Hyatt. 

Month 4

Card 2 - American Express Green Card

Current Bonus: 45,000 points after spending $2000 in 6 months

Round-up: Now, I will say off the bat that the Gold card from Amex does provide 30k more points, but for a fee of $250 as opposed to $150. If that fee difference doesn’t bother you, then go for the Gold card. With either of these, you will receive Amex Rewards points that give you access to the following programs: AeroMexico, Air Canada, Alitalia, Aer Lingus, ANA, Avianca, British Airways, Delta, Emirates, Ethiad, Air France/KLM, Hawaiian, Iberia, Jet Blue, Qantas, Singapore, Virgin Atlantic, Hilton, and Marriott.

Month 7

Card 3 - American Express Hilton Honors Card or Chase Marriott Bonvoy Boundless Card

Current Bonus: 150,000 after $5000 in 6 months or 100,000 after $3000 in 3 months

Round-up: I placed two cards in this slot so that you can choose which of the offers above fits for you personally. The Hilton has no annual fee while the Marriott has a $95 fee. Personally, I prefer the Marriott properties over the Hilton ones on the upper end and the redemption cost, so that is the one I personally lean toward.

Month 10

Card 4 - Airline card based on your location or Amex Gold/Green (one not selected in Month 4)

Current Bonus: 75,000 after $4000 spent in 6 month for the Gold, 60-80k airline miles depending on your program after an average of 4 months

Round-up: This card is going to be based solely on your opinion on annual fees. Some people hate them, others get enough out of the perks from their cards that is more than makes up for the fee. You can also downgrade your card to a no-fee version after a year to remove the fee from your balance sheet. These are all reasons why I would have both the Green and Gold card. If that isn’t for you, then look at your home airport, see what the major airline is, and get the card that fits best with that airline for your own financial situation.

End Result: 84,000 chase points, 86,000 amex points, 106,000 marriott points. The amounts over bonus comes from the points from the spend used to meet the bonus criteria

Part II: Redemptions 

Now the fun part, picking and booking your travel. I love this part of the process as finding the perfect redemption is an extremely satisfying feeling. My biggest piece of advice here is to be flexible. Points availability very rarely follows your exact schedule, so if you have a general time frame and multiple travel options for your trip, the easier it will be to find your ideal redemption.

Another piece to keep in mind is the level of luxury you want to travel in. There are two divisions of points travelers: those who stretch their points as far as possible to go on a high quantity of trips and then those who use their points to afford luxury travel they would not be able to. For example, one traveler might use their 60k chase points to take 10 flights on Southwest so that they never have to pay for a domestic flight, while another traveler might use all 60k points on a one way flight in business class with a lie flat bed and free champagne. It all depends on yourself as a traveler and what your travel goals are. 

Here I want to highlight a couple different types of redemptions that fit into the points we gathered above and show the diverse options you can pick from to start to get your ideas flowing.

Round-Trip to Greece

-Round-trip flight in economy on Emirates out of Newark: 45,000 miles + $126 in taxes

Transfer from American Express into Emirates loyalty program

-2 Nights in Athens: 80,000 Marriott points

Three hotels over 40k per night base level rooms. Two are boutique hotels which will give more of an Athens style experience

-2 or 3 nights in Santorini: 80k Chase points

Transfer from Chase into the World of Hyatt rewards program. Three nights you can spend in beautiful rooms at 25k per night, or splurge to even higher end hotels for two nights at 40k per night. There are around 6 hotels in Santorini partnered with Hyatt, so plenty of options

All-Inclusive in Jamaica

-Round-trip flight in Economy on American Airlines to Montego Bay: 30,000 miles +$140 in taxes

Transfer Amex points into British Airways loyalty program to book American Airlines flight through BA

-3 Nights All-Inclusive: 75,000 Chase points

Transfer Chase points to World of Hyatt and book Hyatt Zilara Rose Hall for 25k points per night

Luxury in Rome

-Round-trip Business Class on Delta to Rome: 100,000 miles + $400

Transfer enough points between Chase and American Express into Virgin Atlantic loyalty program

-Two nights in a 25k per night Hyatt hotel and two nights in a 60k per night Marriott Property

The Hyat points will come from your Chase card and the Marriott points will come from your Marriott and leftover Chase card points. You can mix and match the two if you like your Hyatt hotels better than the Marriott properties. There are a lot of extremely nice hotels under these properties in this area. If you choose to not go to a higher-end hotel, you can stretch out your stay to well over a week with those hotel points. 

Wrap-Up

These are just three examples of the options you have after earning your points doing nothing more than your normal spending. Understand what kind of traveler you are and how you want to spend your points, and this will give you clearer direction on how to go about your credit card rewards strategy. This is just the tip of the iceberg, and I can tell you from experience that once you get started, you will never want to pay for travel again. 

A whole new world is opened up when exploring point redemptions, and there is a ton of information out there that can be very confusing to those just starting out. My goal is to help you all navigate this world as easily as possible to take advantage of the banks and explore the world in whatever style best suits you. 

With that, I will continue to write guides and breakdowns of redemption possibilities for free to help out the community best I can. Feel free to drop a comment or DM on specific items you would like to see me write more in-detail on so that I can provide the most useful content for you all. 

I also have a service I do as a side-hustle on the side where I provide award booking strategy and advisory services tailored to clients. I use their current financial situation, credit, redemption aspirations, etc. and create a step by step plan tailored to the goal they wish to achieve when it comes to points redemptions. If anyone would like more information on that, please email me at BowTiedBully@protonmail.com or DM on Twitter. I would love to work with you to get you the vacation of your dreams at a fraction of the cost!

As always, thank you all for reading. I appreciate the support! Content is always free, donation accepted at the address found in my profile.