Traveling on Points {guest post by Ian}

Hey, it's Ian.

I’ve never written on here before, and I have no clue about any of the rules of blogging or writing - I’m a numbers guy. But Charity mentioned one of the questions she gets asked most is how we finance our vacations with points and get sweet deals. When it comes to trip planning, that's my domain. So I'm writing a guest post.

To cut to the chase, the primary answer to how we get points and deals for travel is: credit cards.

Sure, on a lot of credit cards you get one “point” (for example: airline mile, hotel point, transferable "ultimate rewards" point, etc) for every dollar you spend with the credit card. And in some categories for some cards (like gas, restaurants, etc) you get 2, 3 or even 10 times points for every dollar you spend. But the real mass of our point collection has come from credit card sign up bonuses. With most credit cards, there is a large number of points awarded when you meet a minimum spending requirement within the first few months of having the card.

Sign up bonuses allow for much quicker and more efficient accrual of points than regular matching spending deals. For example, right now the Marriott Bonvoy credit card gives 100,000 points after you receive the card and then meet minimum spending requirements. I would need to spend $100,000 with the credit card to otherwise earn these points (abstracting from any bonus categories). We don’t have this card currently (it just got rebranded, FYI) but just as an example - you get the picture. The boost from bonuses dwarves the points you get from the day to day spending - especially if you are trying to be budget conscious as we are, so you don’t really want to spend much on a day to day basis.

That’s not to say you shouldn’t take the daily spending points earned where you can get them. And being aware of the bonus categories for different credit cards can be pretty huge. For example, hotel credit cards usually provide bonuses when you spend money at their hotels. One time I found myself booked in a Marriott for a few nights for work. I was going to be reimbursed and so I booked it on my Marriott card, which meant I got insane rewards per dollar spent. All told, the time I spent staying at this hotel (paid for by someone else) resulted in roughly one free night for me at some future date at a nice place because I used the right credit card.

In addition, credit cards of certain airlines or hotel chains often come with some type of status, and this can also be huge. This stuff always happens to me by accident because I usually determine the card I will get by the bonus, not by the status ... but it is good to be aware of. On our most recent trip to Tenerife, for example, the status we had (because we had a credit card connected to the hotel chain we were staying at) resulted in an amazing suite upgrade that probably would have cost into the hundreds, if not thousands of dollars. We never would have paid outright for that upgrade, but the resort was happy to give it to us on the basis on our "platinum" status because they were at 40 percent capacity at that time. We also got free breakfast at an amazing breakfast buffet every morning, just because we had a credit card with the hotel chain. Most hotels and airlines are good about reminding you what status you have, and its implications, but it’s good to know in case they forget. Terms and conditions obviously apply.

Some of the credit cards we have used, for illustration, are:

• Chase Ritz Carlton card (no longer available): a few free nights as a sign-up/minimum spend bonus, elite status, travel expense and Global Entry enrollment reimbursement, other benefits. It does have a hefty annual fee to be aware of though (we strategically decided it was worth it for us). We used the free nights to stay in Moscow, Half Moon Bay, and Tenerife.
• Chase Hyatt card: annual free anniversary night, great sign-up bonus, status, and other benefits, with a much lower annual fee. We used our Hyatt bonuses (we both got the card) for our stay in the Maldives.
• Chase Southwest Credit Cards (there are multiple): we used these to get a great bonus and the bonuses helped us to reach the companion pass, which allows a free companion ticket for EVERY flight a person goes on in almost up to two years. This might be the best deal in the credit card world.
• Chase Sapphire cards: allow you to earn Ultimate Rewards points which can be used with various different airline and hotel chains.

There are others we have liked, but this gives you a sense.

I said credit cards are the “primary answer” because we also do a decent amount of homework to get good deals, plan in advance to get cheaper flights, etc. There are loads of times we go on holiday and don’t use points to pay for something. Of course there are also basics things that can help with point accrual, like always putting down your frequent flyer mile number when you book something, or being aware of loyalty clubs that hotel or rental car chains have. We also try to take advantage of random promotions/partnerships that travel companies do. For example, one time Scandinavian airlines had a promotion with Hertz: rent a car and get 10,000 airline miles. We needed to rent a car for a trip anyway, so we found one from Hertz for like $30 and got 10,000 miles for it. Those miles are enough for one free roundtrip flight from Oslo to Svalbard (a trip we've been wanting to take) at some point in the future. Rent four cars during the life of the promotion and you have enough for a family of four to do that for free, rather than shelling out around $1500 for all of us to fly!

Of course, not everyone wants to go to Svalbard, so those Scandinavian airline miles could be useless to some. Which brings me to the point that it’s probably best for you to decide what YOU want to pursue and what points will be best to get you there. Then work towards that goal rather than (1) being driven by every promotion or advertisement - there are plenty of these to keep you busy but they may not actually get you where you want to go, or (2) taking a shotgun approach where you accumulate a few points in loads of different places but never enough to do something with. For us, we have a couple (transatlantic) airline programs we focus on as our primary goal because we know we will go back to the USA once a year, and when we have gotten our reserves to comfortable levels there, then we focus on the “extra” goal of hotel points with a couple chains that we can use for a cool place to stay every now and again.

This approach requires being really organized and on top of payments, etc, and I would say that my approach is not for everyone. Some people will not feel comfortable having multiple credit cards. Some will not want to keep track of when you need to spend what by when, or what cards you have open or closed, or when miles expire and so you need to do something to keep that from happening, etc. And you can get into a lot of long term trouble financially given credit histories and high interest rates on credit cards if you’re not really organized. Essentially, does it take effort to keep track of all of this? Sure. But it’s not work to me. It’s a hobby that I enjoy, just like sitting in a recliner and watching the New York Knicks is for some people. Rather than watching b-ball I do this and it has benefits financially and experientially for our family. And because I am a numbers guy, it's fun for me.

I use several tools to help me keep track of our credit cards and points. Award Wallet is an awesome mobile and desktop app that I use to keep things organized and track points. Then periodically I update a Google Spreadsheet that I created for the purpose of tracking credit cards. I do this during the time that Charity and I set aside on Sunday evenings to go through our budget and check in on our bank and credit card accounts. We would track the budget even if we didn't do any credit card point collection, and so it’s not that much marginal work once the infrastructure is set up.

Many may ask, “how did you start given the vast number of chains and credit card options, and the complexity of the rules associated with them?” When I started getting into this I didn’t know much. But there are some people out there that basically do this for their job and write blogs on it (people have asked me why I haven’t done this and it’s because so many people are already doing it a lot better than I would in the time I would be willing to put into it, so I would just be another copy of essentially all the same info). I subscribe to one of those blogs (Million Mile Secrets) and so I get an email every day flagging different promotions or opportunities. Most days I spend about 20 seconds looking at that email. Every now and again, something pops up that catches my eye. Initially I was investing a somewhat significant amount of time into learning about all this, but after about six months I felt like I had learned the basic tricks of the trade and so now it’s just particular promotions or opportunities that I am looking for. For example, I knew about the Scandinavian Airlines/Hertz thing I mentioned earlier because Million Mile Secrets flagged it, not because I myself checked the Hertz and Scandinavian Airlines website all the time. You can see how these tools that someone has already put the effort into creating can dramatically reduce the workload.

I realize this topic probably lends itself more to Q&A than to someone rambling on for forever ... so if you have questions, put them in the comments section. I’m happy to do a follow up post. (Although judging by how long it took me make the time to prioritize this one, I wouldn’t expect it anytime soon. But someday I’ll get around to it if there is a critical mass of questions :) )