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My criteria is for it to be 100% vacation so no enduring an annoying time-share-type sales pitch (i.e. come stay for free so somebody can try to sell you something) and no work requirement (i.e. travel writing or compensation for reviewing the resort, etc).
For the past year, I have been working on hacking frequent flyer and hotel reward programs. By “hacking” I mean strategically (and, of course, legally) utilizing them to their fullest extent, on multiple levels, which few people even know how to do let alone execute.
This blog post is the result of a year’s research and experimentation. It will show you step-by-step how you can dramatically leverage these programs (even if you don’t travel much) to achieve extraordinary lifestyle experiences quickly and frequently.
Let’s start at the ground level and work our way up…
Even if you don't fly very often, this is the crucial first step and it is free. I am in the United Airlines "Mileage Plus" program which is part of the Star Alliance Network that contains many international and domestic partner airlines (on which you can also earn and use your frequent flyer miles). There are other networks of Airlines too so try to join one that has flights to the places you travel most.
Always try to fly on the airline whose frequent flyer program you are signed up with (or a partner airline in the network so your miles will transfer). If you fly a lot, you will start hitting different 'status' tiers. In addition to the lifestyle benefits of free upgrades to first/business class, free use of lounges on international trips, and other such lifestyle perks, you also begin getting "bonus miles" every time you travel (often 25% up to 100% more than the actual miles you fly, depending on your status tier). The miles will start racking up much faster when you break through to the higher tier statuses.
Just like airlines have frequent flyer programs, hotels also have rewards/loyalty programs. And just like the airlines have partner networks, most hotel reward programs cover a family of hotel brands. I am a member of the Hilton Honors program. The great thing about the Hilton family of brands is that it includes hotels as inexpensive as the Hampton Inn all the way up to uber-luxury hotel brands like the Waldorf Astoria. The beauty of course is that you can rack up points staying at the low or mid-priced hotels (on business for example) and then redeem your reward points for free nights at the luxury hotels.
Like the frequent flyer miles, frequent hotel stays equal more reward points but also allow you to climb to a higher tier status which means bonus points on top of your regular reward points.
Over the past year Hilton Honors has been putting out different bonus offers on their website every quarter (and sometimes more frequently, often multiple different offers at a time that can be used in combination). If you check their website before each stay, you can take advantage of the special offers and rack up the bonus points. As an example, on one 3-night stay this past year ($149/night), I was supposed to get 4,470 Hilton Honors points for the amount of dollars spent (Hilton gives me 10 base points for each dollar spent). However, because I registered for these special offers on the Hilton website (a couple different ones actually applied), I walked out with 14,586 Hilton Honors points (over 300% more)!
If you are travelling and need to rent a car, look on the hotel website where you are a rewards member and see what rental car partners they have where you can get hotel reward points (or frequent flyer miles on your airline of choice if you prefer). Hilton Honors has affiliations with most rental car companies for example and with most of the airlines as well. Incidentally on that same 3-night stay above where I got over a 300% bonus on my points I also walked out of there with 2,500 frequent flyer miles because the airline was doing a cross-promotion that I was allowed to take advantage of as well (score!). You will quickly realize that most of your travel expenses can be converted into either frequent flyer miles or hotel reward points, and often multiplied through special offers and cross-promotions. If you book your travel properly, the points start adding up....fast.
At this point, if you are someone who does not travel a lot you might be feeling that the international luxury vacations are unattainable for you because you cannot rack up enough miles/reward-points on travel expenses, even with these point-multiplication techniques. Fear not! We are just about to get to the good stuff.
And for you road warriors who already have your travel rewards fully optimized, get ready to take it to the next level…
There is a program called "Rewards Network" that restaurants, bars, clubs, lounges and other food/beverage establishments sign up to be part of—offering frequent flyer miles or hotel reward points every time you dine there on a per-dollar-spent basis (including tax and tip). Most of the major hotel reward programs and frequent flyer programs are part of it, having named it after themselves on their website (ie: "Hilton Dining") and you can only join through one rewards program per credit/debit card.
So, I have joined "Hilton Dining" with my credit card and "United Dining" with my debit card. You register your card online when you sign up for the program and then every time you patronize a participating establishment, you simply pay with the card you registered and rack up the points or miles automatically (no need to even tell anyone at the restaurant you are a member as the use of your card alone triggers the points or miles to be added to your account). The really cool part is that there is an iPhone app for the Rewards Network, so whatever city you are in, you can literally just search for restaurants "near you" that are in the program (just like you would with Yelp). As with the other reward programs, there is a tier level here too and you get more points per dollar spent after you have a certain number of "dines".
Most of the major hotel reward programs and frequent flyer programs have an online 'shopping mall', which is basically just their affiliate links to all the major retailers. The value proposition is that if you buy through their affiliate links, they will give you reward points (or frequent flyer miles) for doing so on a per-dollar-spent basis. This is huge. Almost everything you purchase in your regular daily life (from designer clothes to shampoo to baby diapers to running shoes) can be purchased online and delivered to you. Be strategic here because this is a big ticket item. If you start buying everything from your toiletries to your Nordstrom clothes to your Best Buy plasma TV to your holiday gifts and birthday presents online, and you do it through the affiliate links of your chosen hotel reward or frequent flyer program, you will start to rack up points or miles incredibly quickly.
I got the Hilton Honors Am/Ex Card with no annual fee. In addition to the 50,000 initial free points I got for joining, my card offers me 3 Hilton Honors points for every dollar spent, plus 6 points per dollar spent on certain items (like groceries, stays at the Hilton, etc). So, this is a way to get additional points on top of what I'm already getting when I dine, shop, rent a car, stay at a hotel, etc. In the example above when I got 14,586 HH points for my 3 night stay, I also paid for that with my HH Am/Ex card, which got me an additional 6 points per dollar spent or 2,682 points. So, I really got a total of 17,268 HH points plus 2,500 FF miles for one 3-night stay (Not bad!) When I dine out at participating Reward Network restaurants, I get 8 Hilton Honors points per dollar spent, but by using my HH Am/Ex card I get 3 points per dollar spent on that side, so that is a total of 11 points per dollar spent. Same with the online shopping, etc.
Where do you want to go, and what hotel do you want to stay in? (I had initially picked out a 6 night stay at the Waldorf Astoria in the Maldives, printed out pictures and put them on the fridge). How many hotel reward points and frequent flyer miles will it take to do that? (By going on the border of the 'low season', I estimated that at about 240,000 points and 75,000 FF miles).
Get your numbers, set your goals, put them on the refrigerator. Then, see how you can restructure your regular life expenses as well as your business and travel expenses to maximize your reward points and frequent flyer miles.
My guess is you can dramatically increase both FF miles and hotel reward points on a monthly basis just by making some minor adjustments to HOW you purchase what you are already buying.
We are not a tax professionals, this is not tax or legal advice, and tax laws are constantly being changed and revised and may change the day after you read this. So, this is for informational purposes only, and it is your duty to consult with your own tax professional about your individual situation and the most updated applicable laws before attempting to implement any of the content in this post.
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