An Introduction to Stackable Deals

Are you maximizing the money that you spend on travel?  What if for every dollar you spent on travel, 75% was reapplied toward future travel?  Though often a bit more modest and in the 5% to 20% range, these types of "double dipping" opportunities do exist through stackable offers and promotions.

The Double Dip

It is rather common for travelers to double dip on travel spend without even thinking about it.  Consider the following.  I pull up Marriott's website and make a reservation at a Courtyard property and pay with a point-earning credit card such as the Chase Sapphire Preferred.  I've not only earned 10 Marriott Rewards Points per dollar on the base room rate, but I've also earned 2.14 Chase Ultimate Rewards points per dollar on the entire bill including tax.  Even if I assign very conservative values to the points earned (say 0.5 cents each for the Marriott points and 1 cent each for the Ultimate Rewards points), I'm still able to reapply 7% of my travel spend toward future travel.  Not too bad, given my limited strategy...but we can do better.

The Triple Dip

Intentionality begins to show when we advance to triple dipping.  It comes in many forms and involves additional strategies such as using online shopping portals to earn cash back or additional points/miles, registering with hotels and airlines to take advantage of the occasional travel promotion (such as Marriott's "Megabonus" to earn a free night after 2 stays), and buying Marriott gift cards to earn the occasional purchase bonus (such as 12 Southwest Airlines points per $1 in Marriott gift cards).  By taking advantage of existing opportunities, one can easily multiply the value of their travel spend.

The Quadruple Dip
When the stars align, it's quite simple to stack multiple offers and transform a triple dip opportunity into a quadruple (or better).  Using the above examples, a best-case scenario (which I was personally able to take advantage of in 2013) would allow you to do something like this and reapply more than 75% of your travel spend toward future travel:

1. Register for Marriott's seasonal/quarterly travel promotions (50% return* through Marriott's "Megabonus")
2. Purchase Marriott gift cards to earn Southwest Airlines points (17% return**)
3. Use a points-earning credit card to purchase the Marriott gift cards (2.14% return***)
4. Initiate the Marriott reservation through an online shopping portal (2% return through Ultimate Rewards, 2.5% through Ebates)
5. Earn Marriott Rewards points and credit for your stay (5% return)

Hopefully, this example will help you begin to mentally stack existing opportunities and actively maximize the return on your travel spend.  A good place to start the process is www.evreward.com to compare payouts from various online shopping portals.  Keep in mind that while you may be able to squeeze more travel out of each dollar, the initial cost is still very real.

* Marriott Megabonus earns a free night at a category 1-5 property (worth up to 25,000 points) for every two separate paid stays (could earn up to two free nights during the promotion, which could be maximized by paying for four cheap nights and redeeming for two nights at a more expensive hotel)
** Southwest Airlines points are valued at 70 per $1 giving each point a value of $0.0143 (1.43 cents)
*** Chase Ultimate Rewards points constantly provide me with a value of at least $0.02 (2 cents) through Hyatt, United Airlines, and strategic British Airways transfers