How to beat limited award availability once and for all

It's one of the biggest quandaries in the world of points and miles: The more desirable a destination is, the harder it is to get there in a premium cabin (generally speaking). First class to Australia? Good luck. Business class to South Africa? Prepare to pay up. The problems are magnified when you start looking for premium-class awards as a party of two, three or even more travelers.

That's why I recently started taking an entirely different approach to using my points and miles: Let the availability decide the destination.

Here's how this has transformed the way I travel with my family.

Some context

Let me start with some context for my family's travel habits. There are some travelers who would never use their hard-earned points and miles for a premium-class flight. They'd rather take 2-3 trips in economy than a single trip in business class.

We are not those travelers.

I love the fact that travel rewards credit cards and loyalty programs allow me to book flights and hotel rooms that I'd never be able to afford if I paid cash. Sure, I occasionally use my points and miles to cover an expensive economy flight, but for the most part, I strategize my earning to maximize my burning — and burning points is almost always directed at premium cabins.

However, this became noticeably harder a little less than three years ago, when my daughter turned two and started requiring her own ticket (boy, that was a bittersweet day). Suddenly, I needed three business-class award seats instead of two. That's a massive increase when you're trying to book long-haul, international flights for your entire family using points and miles.

Our new approach

In the past, our trip planning might have gone something like this:

Me: Where do you want to go for our next trip?
My wife: How about (insert country/city here)?
Me: Sure, let me figure out how to get us there

(Nick searches award availability)

Me: Got it! Here are the dates.

Now, we do things a bit differently. The last few trips have all started with a simple question from my wife: "Where can you get us using points and miles?"

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This approach recognizes that the hardest aspect of booking premium-class award flights for multiple travelers is snagging seats on the long-haul segment. After all, short-haul business class within Europe or Asia is almost always available using points and miles, but the same can't be said for transoceanic flights. So rather than focusing on a specific destination and figuring out how to get there, we now find the award availability first and then branch out from there.

Here's how we do it.

Finding award availability first

My initial quest is to figure out the most convenient, nonstop, long-haul flight with at least three business-class award seats available. However, if you're still learning the ins and outs of this hobby, you may need help figuring out which airlines fly which routes before you can even think about availability. One of my favorite sites for this purpose is FlightConnections.

If you've never used the site before, it's a map-based platform that pulls in flight schedules from hundreds of airlines all over the world. You can filter by major alliance or individual airline, and once you've zeroed in on a specific route, the platform will give you a list of airlines that fly it and even a calendar view of when each flight operates.

For example, let's say you were in the Chicago area and were planning your next trip. If you zoom in and click on Chicago-O'Hare (ORD) on the map, the results will be a staggering mess of lines that touch every continent on the planet not named Antarctica.

However, you could filter down to just Star Alliance flights (for example) or even those operated by a single carrier. And when you click on an individual destination, the flight options will populate on the left, like this example from Chicago-O'Hare (ORD) to Paris (CDG):

From there, it's up to you to find the award availability for the flight you want.

Here are some suggestions for the best ways to do that:

• Use ExpertFlyer to search awards and set alerts
• Star Alliance: Use United, Aeroplan or ANA
• SkyTeam: Use FlyingBlue, Delta or Korean
• Oneworld: Use Qantas, British Airways or American

If you only have loyalty account balances with one or two airline programs, this task may be simultaneously simpler yet more challenging. After all, you're restricted to booking the airlines that partner with one of those carriers. This is why transferable point currencies are so valuable. Instead of restricting you to a single program's rules, award pricing and fee scheme, you can first find availability and then determine the best way to book.

So what does this look like in practice? Here's an example from my yearly Thanksgiving trip to Europe.

How I've done this

In early 2018, my wife and I started planning that annual November getaway, and she started with the aforementioned question: "Where can you get me using points and miles?" Being based on the Treasure Coast of Florida gives us some great airport options for international flights, such as Fort Lauderdale (FLL), Orlando (MCO) and Miami (MIA) — all within a two-hour drive of our house.

I was already very familiar with the various route networks from these gateways, so I started checking options for us to depart on either the Thursday or Friday before Thanksgiving and return the Sunday after the holiday. After just a bit of searching, I found the following long-haul, nonstop flights with three award seats available in business class:

• Swiss Flight 65 from Miami (MIA) to Zurich (ZRH) on Thursday Nov. 15, 2018
• Austrian Flight 97 from Vienna (VIE) to Miami (MIA) on Sunday Nov. 25, 2018

Since we had already visited both of those cities, we pulled up FlightConnections, this time with very narrow search parameters: What connecting flight options would we have out of Zurich on Friday, and how could we get into Vienna on Saturday afternoon/Sunday morning to catch the nonstop flight home?

I typed in "ZRH" at the top, then filtered to only show Star Alliance flights.

Finally, I zoomed into the continent of Europe, and my wife and I discussed the options. We ultimately decided on Belgrade, Serbia, for our initial destination. FlightConnections indicated that there was an early afternoon Swiss departure that was timed perfectly with our trans-Atlantic flight, and (not surprisingly) it had availability in business class.

We repeated the exercise with the return flights, eventually settling on Ljubljana, Slovenia, thanks to the nonstop flight on Adria Airways to Vienna the Saturday before our flight back to Miami. This would even allow us to enjoy a quick overnight in Vienna, though bear in mind that Adria is no longer in operation. (It's also worth noting that Austrian would ultimately drop the VIE-MIA flight to seasonal, so we wound up flying through Munich (MUC) with the long-haul flight on Lufthansa.)

I transferred American Express Membership Rewards points to Aeroplan to book the outbound flight for just 55,000 miles per person plus minimal taxes and fees. Then I topped up my United account with a transfer from Chase Ultimate Rewards to book the return flight through MileagePlus — which required 70,000 miles per person but had no fuel surcharges.

Voilà! We were booked.

Bottom line

Trip planning can be an enjoyable exercise for some, while others dread the process of researching and booking a vacation. However, I've found it to be immensely exciting in recent years to let business-class award availability plan our ultimate destination(s). In the above example, we didn't set out with a preconceived notion of visiting Serbia and Slovenia, but because those cities were easy connections with the long-haul flights on which we found award tickets, it fell into place perfectly — and it was an amazing trip.

We continue to use this strategy for upcoming vacations. We'll be visiting Northern Italy this Thanksgiving and traveling to Vietnam and Cambodia in May-June 2020. For both trips, we first found long-haul award tickets and then selected the destinations.

If you're struggling to figure out where to go on your next trip, give this a try. You may stumble upon a new favorite city — and can get there and back in comfort.