My Six-Year Plan

My wife and I are taking a first-class overseas trip in 2012. And we're hoping to get someone else to pay for it.

Thank you, affinity programs
Our goal, you see, is to earn enough miles and points to have expenses covered well in advance, even if we haven't exactly decided on a destination. Don't think that's possible? Allow me to show you how we did it.

Me: "Let's take a vacation in six years."
My wife: "OK."
Me: "Where should we go? I like Australia. And London."
My wife: "Yeah, but I might want to go to South Africa on safari."
Me: "OK."

Getting started
Two minutes of chatting it up with my wife told me all I needed to know to begin formulating a plan. The relevant questions are:

• What airline serves Australia, London, and South Africa?
• What hotel chain has locations in London and Australia? (We have very close friends who live in South Africa.)
• How many points would we need to fund first-class flights to each location and back? And what is the cost per night for first-class hotels in London and Australia?

Time to take inventory
With those questions as my guide, I decided to take inventory of all my points from every travel partner. Here's my list, beginning with the airlines:

And here's what I have with the major hotel operators:

If you're like me, both Hilton and Virgin jump right off the page since they already have the most miles and rewards accumulated, respectively. Better still, Virgin has flights from London to both Sydney, Australia, and Cape Town, South Africa. And, of course, Virgin flies daily between London and New York. Hilton also has a wide footprint, and the Sydney Hilton looks very appealing. So does the Waldorf Hilton in London.

A little more research
But, alas, there's more to do. Pricing the trip is next on the list. That means estimating how many flights we'll be taking as well as how many nights we might spend in each location.

I'm guessing this trip won't be much different than our last. If so, we're looking at 13 days, with four days of travel time for long-distance flights. A call to Virgin reveals that long-haul trips in the upper-class cabin currently cost 90,000 miles each way per person. New York to London sells for half that. If those rates remain constant, here's what the math looks like:

As for the hotels? Well, if we're in the air for four days, we'll need to book a room for at least eight nights. Unless, that is, we go to South Africa, in which case we'd only need a room in London. Still, it's worth planning for the worst case. The hotels I'm eyeballing run 40,000 HHonors points a night. That's 320,000 points for eight nights.

A long way to go
If all that sounds somewhat daunting, it is. I need to collect 860,000 points by 2012. Frankly, that may not be possible, but I've got at least an outside shot. My American Express card awards us Membership Rewards points on everything, and double points for everyday items such as groceries. What's great about Membership Rewards is that the points can be exchanged for almost anything, including Virgin Flying Club miles and Hilton HHonors points.

Plus, my new Hilton HHonors Visa Card will get me at least two points per dollar spent on business purchases. That won't be thousands, but it'll make a dent over time. Best of all, I've already banked 134,226 Membership Rewards points. Add that to what I have already with Hilton (34,996) and Virgin (24,881), and I'm at 194,103 today. Only 665,897 points to go, or 9,249 per month through 2012.

Let the saving begin
I know what you're thinking, because I'm thinking the same thing: There's a good chance we'll need to save some moola to make this trip happen. And that won't be easy with the $60,000 in debt we've collected.

Nevertheless, I choose to view this situation optimistically: Having a goal will force us to pay down debt aggressively. And doing so will free up cash previously applied to interest, which we can then push into a long-term savings vehicle to help fund the trip in case we come up short on our rewards plan.

On our way
My guess is more than a few of you are thinking I'm crazy to plan a trip six years out. You may be right, of course. But I believe that vacations are no different than any other big purchase; poor planning can cost thousands.

After slumping back into debt recently, you'll have to pardon me if I choose not to be the sucker who pays full price for, well, anything that I don't have to. From now on, I want the best deals on everything.

If that's you, too, or if you just want some Foolish advice about how to make the most of your moola, may I suggest Motley Fool GreenLight? Our soon-to-released money-management service will feature the best tips Fools have to offer. Click here to learn more without spending a dime. And then keep checking back in here. I'll update our progress as often as there's interesting news to report.

Fool contributor Tim Beyers would love to visit all seven continents before he dies. Wouldn't you? Tim didn't own shares in any of the companies mentioned in this story at the time of publication. You can find out what is in his portfolio by checking Tim's Fool profile. The Motley Fool has an ironclad disclosure policy.