Maldives? Cape Town? Tokyo? New York City? Wherever you want your points to take you, there’s one hurdle which everyone must summit: availability. See, when you’re splashing out $10,000 or more bucks for the same trip you can pretty much pick your dates, but when you’re getting that much value, essentially for free, they make it much harder. Here’s how to maximize your opportunities…

Earning Points Can Never Start Soon Enough…

Is there such a thing as too many points? I think not. The sooner you start earning, the more cards you can grab with maximum points and sign up bonuses, responsibly and the more you can earn additional points from your travels. Plot your dream trip as soon as possible, figuring out which cards will offer the greatest benefit. For example, if you want to stay at the Park Hyatt in the Maldives, maybe grab a Hyatt card. If you want to fly Korean Air first class to get there, grab a Chase Sapphire Preferred or Reserve card, which transfers to Korean points.

Position A: More Than 365 Days Out…

Many (but not all) airlines make seats using miles available roughly 335-355 days out. To pinpoint the exact timing, go to make a booking using miles and see what the last available date is, and plot from there. Many airlines offer at least 2 seats in each cabin on every flight using miles when the date is released in that 335-355 range. If you’re ready when seats are released you win. That’s position A, but for most, we go to position B…

Position B: Anytime 355 Days To Weeks Before…

When (if) the initial seats or hotel availability disappear you’re not out of luck. Far from it. Airlines and hotels release those first couple seats or rooms as a courtesy, but from then on they tinker. If you’re planning a trip in prime “spring break” time, you’ll face a tougher battle than an epic trip just a week later. If possible, try to stagger your dates from the pop culture schedule even just a day or two. It really helps. Successful booking in this time frame benefit from getting creative. Look for possible connections, alternate partner airlines, routings and other opportunities to get there in comfort, just perhaps not the way you initially expected. 

Position C: For The Flexible, Last Minute Can Be Great…

Here’s the great divide. Most people HATE last minute and the thought of potentially not going, or having plans change gives people anxiety. Many airlines and hotels however are generous with seats or rooms using points at the last minute, as they realize things won’t go full. Spend time researching which airlines or hotels open up space last minute. Cathay Pacific, which you can book using American Airlines and other miles is generally excellent with releasing seats in the week and even days before travel. Never give up…

The Big, Great Tip You’re Looking For…

You can always improve a reservation made with points and miles. For airlines It’s actually much easier and cheaper than changing a reservation made with cash. An issue I find with many consulting clients is that they want to fly business the whole way, but at the time of booking one connection will be economy. We lock in the business while it’s hot, settle for the economy connection and set alerts for when and (if) the economy segment hopefully opens business space. For hotels, you obviously want to use points to stay for free, but if you find a hotel you’re willing to pay for if the trip is on the line, it can never hurt to book a refundable rate, just to lock something in. If you decide you’ll need to stay and pay, you can always cancel the refundable rate and rebook the cheaper rate. If a hotel with points opens up last minute, you can cancel risk free…

And How To Win Whenever You Start Planning…

Now that we’ve made all of you feel good whether you’re a 355+ day planner or a 21+ hour planner, we can get into the real deal. This whole free vacation thing is cut throat, and the more peak a time you’re looking to travel, the worse it is. You NEED to use pro tools like ExpertFlyer to set alerts for the seats you want. You need to explore all routing possibilities, you need to see which credit card programs offer the best rates for what you want and you need to practice. You absolutely do not want to be looking up how to book partner flights on the day of the event. Practice makes perfect…