Travel Hacking Strategy

Travel Hacking Strategy

Hello $wanigans! Welcome back. Today I have a follow up post on travel hacking. Recently I wrote an article on how Lucy and I will travel hack our way to a free Greek vacation. This post presented an overview of our plans, a history of our travel hacking experience, and the successes and failures along the way.

Today I wanted to go more in depth on how we plan to accrue points and miles to ensure a free vacation getaway to Greece. There isn’t anything special about Greece in this process. If you do so desire, you could employ similar strategies for many other vacation destinations. For Lucy and I, we have chosen to take a Greek vacation next year in celebration of our ten-year anniversary.

There is no other science behind travel hacking specific to Greece. And as always, be sure to check out the comments of today’s post as well as my prior post on travel hacking as the enlightenment from the community of readers is half the value (for instance, just peak at the Greece travel itinerary Jason shared in the comments on my prior travel hacking post)!

Prior Cards Hacked

Travel Hacking StrategyWe’ve turned on the travel hacking spiguet pretty close to full blast within the last couple years. A major boon to us in this regard is our daycare accepting credit card as payment with no additional fees. With two kids now in daycare, this amounts to nearly $20K in annual daycare spend, ripe for the picking of bonus travel cards! And this is in addition to other normal spend we put on a credit card on a day to day basis.

Needless to say, we’ve hacked a few cards already. For both Lucy and I, the list includes all the big hitters in the bonus mile space such as the popular Chase Sapphire cards, CapitalOne Venture, Barclaycard Arrival, Citi American Airways and many others. The good thing for travel hackers is that there is a plethora of cards available to hack. We utilized ~$700 of travel rewards in 2014, nearly $1,000 in 2015, over $3,700 in 2016, and about $3,200 in 2017.

Reward cards provide points/miles in various forms. Some require direct travel purchase reimbursement for travel related purchases (e.g. airfare, hotel, rental cars) put on the card (e.g. CapitalOne, Barclaycard), others provide immediate redemption for travel purchased through their portal (Chase, AmEx portals), others provide miles through specific carriers and are connected to your frequent flyer account (e.g. the Citi AAdvantage), etc.

We’ve been pretty agnostic of the form the miles come in as we’ve been able to general get good use out of them any which way. And we churn through them fast enough that we know we’ll eventually touch most all the popular offers. Our baseline annual travel includes two trips back to the midwest to see family which includes 3 airplane tickets now that our oldest son is over 2 years. Other rewards have been used for weekend getaways to see friends and family for various things like weddings and corresponding bachelor parties, etc.

This is a long way of saying that if we can earn some bonus miles, we’ve been able to use them fairly easily and quickly. Obviously it does little use to travel hack credit cards when you don’t travel much…

The Framework for New Cards

Travel Hacking StrategyWhile we have a long list of cards previously hacked, there still remain numerous cards out there to be hacked with still solid bonus reward potential.

Since we have a specific and fairly expensive trip upcoming to Greece, we know how and who we will be spending points through. Specifically, we’ll likely be booking our airfare through American Airlines and our hotels through Marriott / Starwood / AirBnB.

American Airlines is a hub in Charlotte, so we know any points that go unused on the Greece trip will be used later on with airfare back to the midwest. Our AA frequent flyer accounts get used regularly (for personal and work related trips) and so there is no possibility of our accounts going inactive and losing said reward miles.

With Marriott / Starwood, the same goes. These hotels are everywhere in America and increasingly so internationally. For work or pleasure, we’ll continue to maintain active accounts with these businesses.

With that said, we feel comfortable targeting American Airline reward cards and Marriott / Starwood reward cards (Meaning the bonus rewards come in the form of frequent flyer or preferred guest rewards for these respective companies), and general travel cash back redemption cards.

Cards to be Hacked

First the starting point is our current rewards stashed to date. Between Lucy and I we currently hold a combined 260,000 Chase Ultimate Reward points (available to be redeemed for travel purchased through the UR portal) and 200,000 American Airline miles. Not a bad starting point (probably enough as is to pay our Greece vacation), but our goal is to accrue points between now and the vacation (Sept 2018) to pay our way. Our current stash will be used for our normal annual travel home, weekend getaways, etc.

With the framework laid out above (and the history of cards we previously hacked and thereby reducing the pool of future cards), we’ve identified a few cards we’ll focus on in the next year. One caveat that I need to mention is the added flexibility that being able to apply for small business cards can offer in travel hacking strategies. Don’t have a small business, don’t be so sure. A small side hustle may allow you to qualify for a small business card. It is less intimidating than you may expect. And if you are a serious travel hacker, this gives you a wider array of cards to open to maximize your rewards without much of a risk of running out of cards (most cards allow you to cycle back through them and be eligible for bonus offers again after two years).

Lucy and I began opening business cards earlier this year and we’re very glad we found this option. We’ve done a lot of the consumer cards so the business cards is what we’re currently churning through.


Travel Hacking StrategyThat list stars with the Business Gold Rewards from AmEx. This comes with 50K Membership Rewards (“points”) which are universal (can be used on any airfare / hotel, etc), but our intention will be to book our flights with these membership rewards. 50K rewards for each Lucy and I (churning the card for each of us separately) may not be completely enough for airfare, but the backup option could be using our Chase Ultimate Rewards or American Airline points we’ve built up.

This card comes with a $175 annual fee, but it is waived in the first year which is a consideration we focus on. This will work perfectly as we’ll book our travel before the next year fee hits and then either cancel the card or, if in the future we end up opening another AmEx card (e.g. a free card), we could always transfer the remaining Membership Reward points to the new card and cancel the initial card.

Another option we are still considering was brought to our attention by Mr. Pie in the comments of my prior post on travel hacking Greece and that is applying for a card with British Airway Avios points which can provide cheap access to Europe (e.g. Dublin for 27K points per Mr. Pie). From Dublin airfare to Greece is fairly cheap. The BA Signature Visa offers 50K points with $3K spend (plus $95 annual fee). Getting nearly two flights out of this would be nice! Thanks for sharing this option, Mr. Pie!

Capital One

The next card we’ll likely open was mentioned by Mr. Pie as well which sparked our attention. He mentioned that instead of utilizing hotel reward cards for accommodations to use cash back cards like the Barclay Arrival Plus and various Capital One cards to reimburse for AirBnB instead of more expensive Marriott / Starwood hotels. Upon a brief search, we like this idea as we can get some great AirBnB options at reasonable prices. But like I mentioned above, I’ve already churned through these cards…but not the Capital One Spark cards for business!

There are two types of Spark business cards, one offering $500 cash back and the other for 50K travel miles which can be reimbursed for any travel expense (including AirBnB). These cards require $4.5K spent in the first 3 months to earn the bonus, but the annual fee is waived in the first year. So between Lucy and I, we have four cards to earn a total of $2K worth of rewards for hotels or AirBnB.


Beyond the Amex and CapOne cards mentioned above (which will keep us busy over the next 6-9 months), we’ll then consider a hotel card like Starwood. While Marriott and Starwood merged last year, they retained their separate loyalty programs (transferrable between each other) which will remain as such going forward with new card agreements expected to be announced in early 2018. I’ll keep my eye out for some good bonus offers!

Our preference here would be the Starwood card for starters as the current offer for bonus miles (25K SPG points) is similar to the current Marriott offer (80K points), but Starwood waives the annual fee in the first year and Marriott doesn’t. Depending on the redemption value of SPG points (which varies among hotel class within Starwood), these points could be worth ~$500 or more.


So that’s the tentative plan right now! Rack up some AmEx MR points to be redeemed for the airfare, hack the CapOne Spark cards & the Starwood SPG cards for the hotels. Do you have any other ideas we should consider? Let us know in the comments below.

We’ll keep you posted along the way, especially if plans change! 

Thanks for taking a look!

The Green Swan

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  1. Thanks for sharing your strategy. We are new to travel hacking and are taking advantage of the chase cards first. We are almost at the $4k in spending on our first card. The holidays helped. It looks like we will open 7 cards per year between the two of us. I love the idea of taking the $5k that we were spending in travel and adding it to our asset allocation.

  2. I really need to get on the travel-hacking bandwagon but I’m-a-procrastinating big time.

    Question – my assumption is that you have to start an online account with all of these cards, entailing a new username/password etc. It may sound like a silly question, but how much extra chaos has this created for you? Do you just manage it all in a spreadsheet as I’ve heard others mention? Also, do you worry about the extra hacking-risk of having all these extra accounts?

    1. You do need an account for each card company but, for instance, all Chase cards are under the same account.

      There is definitely added chaos by the process but it’s been manageable. I’ve been tracking the cards in excel lately with key things to note including setting auto payment of balance in full, when the rewards are earned by, and when the next annual fee hits.

      I have ID protection so I don’t worry about the risk too much. Plus I do actively close cards once rewards are used which reduces the risk.

      Lastly, our credit scores have not been negatively impacted at all. Mine is in the high 700s and Lucy’s is over 800.

      Thanks for the questions!

  3. Hey, JW! Mrs. G and I are very intrigued by travel hacking. But we just don’t know if we have the bandwidth to do it in 2018. We’re going to be building a house in the Wake Forest area so we’ll have our hands full. But 2019? That could be the year of our travel hack. Looking forward to how you and Lucy manage the Greece hack. Thanks for sharing, my friend. And Merry Christmas to you, Lucy, and the cygnets. Cheers.

    1. It can be a bit intimidating as you start to wade into the travel hacking waters, but you folks are so on top of things I’m sure you won’t have any hiccups. But I understand you’ll certainly have your hands full in 2018 building your own house, how exciting! When you’re ready to get into travel hacking though we’ll have to chat. Take care Mr. Groovy and Merry Christmas to you and Mrs. Groovy!

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