Managing a Milestone

Even though debt has me down, I'm determined to take my wife on a first-class vacation for our 10-year anniversary.

So far, it's looking good. For seven nights in October, we'll be staying on Waikoloa Beach on the big island of Hawaii at a top resort. And the price for all this? Less than $250.

Wait, did you say less than $250?
Yep. Here's how.

Remember when I wrote that hotel programs are likely to give you more for your mileage dollar than the average airline? That's especially true of Hilton (NYSE: HLT  ) , though I've also had luck with programs run by Marriott (NYSE: MAR  ) and Intercontinental Hotels (NYSE: IHG  ) , which owns both the high-end InterContinental chain as well as the Holiday Inn.

But it was Hilton that won our business by offering a seven-night deal at its Waikoloa Beach resort for 205,000 points. The beauty of this arrangement is that I needn't have all 205,000 points right now. I'll order the certificate when I have them in my account.

That won't be long from now. My HHonors account has 96,000 points as it is, and I have more than 146,000 points available in my Membership Rewards account -- the affinity program American Express (NYSE: AXP  ) offers to its cardholders.

American Express and Hilton have an arrangement whereby I can transform Membership Rewards points into HHonors points at anytime. But it's actually better than that. Hilton offers American Express cardholders like me a 30% bonus. Do the math. We need to transfer just ... (key-punching sounds) ... 84,000 points to get our king room in Kona.

Total spent: $0.00.

Now, it gets more difficult when it comes to the flights. Why? Airlines have become tightfisted when it comes to giving out miles. And the majors, including UAL's (Nasdaq: UAUA  ) United and AMR's (NYSE: AMR  ) American, have begun to set expiration dates for miles they first handed out years ago. Dec. 31 will be a date of reckoning for many.

For us, too. My wife has more than 33,000 miles with United's Mileage Plus program that will disappear come December. My 32,000 miles only have till next August. It's time to use them or lose them. So, we're using them. But United requires us to have 35,000 each to book coach seats to Kona.

No problem. United allows its members to buy up to 60,000 points annually. I ordered the 5,000 we'll need this morning. United says that they'll be available 48 hours from now.

Total spent: $214.

Follow the money
Is booking free travel really this easy? Yes and no. Yes, because the right frequent-guest program can give members lots of options. No, because airlines will often load down their programs with restrictions. Here are two tips for making the most of your miles when booking travel arrangements:

  • Get a flight first. Book your trip around what's available from your favored airline. Hotels are always more likely to have rooms on the date you'll be available to travel.
  • Be flexible. Airlines prefer to keep mileage travelers away from their most profitable flights. As such, your best bets will be Saturdays, Sundays, or the middle of the week. (We're hoping to leave on a Saturday and return on a Saturday night red-eye.)

Need more money tips? Consider Motley Fool Green Light, our personal finance service, where co-advisors Dayana Yochim and Shannon Zimmerman show you how to unlock the fortune hidden inside your paycheck. You'll find nearly $500 worth of advice in the July issue. Get your copy and 30 days of unfettered access to the service, free, right now. There's no obligation to subscribe.

Fool contributor Tim Beyers writes weekly about personal finance and investing basics. Have a Foolish money tip? Tell him. Tim didn't own shares in any of the companies mentioned in this article at the time of publication.

Find Tim's portfolio here and his latest blog commentary here. Order up a few drinks if you'd like The Motley Fool's disclosure policy to tell you about its days strolling nude beaches in the south of France.

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