How To Start Planning an Award Trip

Kai asks on the FAQ page advice for planning an award booking. He says;

I have some miles, I know where I’m leaving from, and where I want to go. But there seems to be a lot of possibilities in between using stop-overs, open-jaws, or routing rules that can take you across continents. How do you start filling the blanks in an attempt to fully utilize the miles?

If you’re not familiar, I did an Introduction to Airline Stopover and Open-jaws. But if you’ve seen the list of stopovers, or some of the crazy United stopover posts, you know things can get crazy. Some airlines allow a ton of stopovers, and even the ones that seem normal can be insane. How do I decide to book what, given all the options?

1) Where do you want to go? You said you already know that, but I really mean that it’s the first step.

You can do anything you want, even if it’s poor use, you could just book oneways with miles to see all the things you want to see, right? So just because you can get some stopovers doesn’t change what you want to do.

For most people that has to do with time. Trust me, nearly everything is possible. But if you have two weeks, where do you want to go? Greece, Italy, both? That’s step 1.

Stopovers are then a tool to see all those places for fewer miles.

If you want to spend your entire two weeks in Italy, do it! It’s a great country. If you want to see Spain, Italy, and Greece in one week, also do it.

2) Given the miles I have, what can I do?

Personally, I feel like I can always come back later if I miss something. So I focus on doing as much as I can, but I don’t fret. Again, that’s up to each person’s philosophy.

I am a deal-chaser though. Like this summer I really want to do parts of Europe I haven’t done. But that’s a lot of area.

Here are the places I’d like to go:

• Scandinavia (mostly Norway)
• Spain and Portugal
• Croatia and Montenegro

I’m not sure what my schedule will look like but it’s possible I’ll only choose one this summer. I will eventually do all 3, and I want to go to them all equally.

However, I have a lot of Club Carlson points that need burning, so I’ll likely just blow them all in Scandinavia while I have the chance. The others will always be cheap, so I see this as an opportunity to seize.

But if a bunch of InterContinentals in Spain went on PointBreaks this July… that would be really tempting as well.

So in this case I might start filling in the hotels and then start filling in the flights. (Europe is easy, I’d probably use Avios or discount airliners).

In the case of going to Bora Bora, that’s my destination and I may or may not be able to fit in stopovers along the way in crazy out of the way places. It will depend on what United feels like booking and what awards Air New Zealand gives me.

3) Finding stopovers

Regardless of what destinations I’ve decided on, you can find a way to do them all with stopovers.

Let’s say I wanted to do Scandinavia and Spain. Easy, I just need to:

1. Look through the miles/transfer partners available with my points, and then…
2. Look at the “Cheapest Miles to” posts to see which are the most competitive options. And then…
3. Compare to the list of airline stopovers

Already I know that I have United miles, it’s only 60k roundtrip, and I’m allowed 1 stopover and 1 destination. Totally enough to do both.

This really is an accurate process for me. I just look at what I already have. I have a ton of United and AA miles because they are easy to get. Sure AA doesn’t allow 7 stopovers but I have a ton of miles and it gets me to Europe for cheap.

4) Stopovers are big, but open-jaws are bigger

Practically speaking, most everyone allows open-jaws. Even if you just book your own oneway to Paris and then another back to the US from Rome, you’ve just created your own open-jaw.

And if you think about it, open-jaws are endlessly huge. Between Paris and Rome you can see as many cities as you want.

So let’s say I wanted to do Scandinavia, Spain, and Croatia. Even with still using United miles and not jumping to an airline with more stopovers, I can make the trip happen on the open-jaw alone.

Of course, I’ll have to fill in the gaps with other miles, but at least I get to see all three. And given that tickets can be cheaper in Asia and Europe, it’s more important to get the longhauls taken care of with miles.

Most every long international trip we take involves an open-jaw of some sort so we can get around the region without back-tracking.

5) Fill in open-jaws

At this stage I’m just connecting the dots if there are any left. Just making sure I’m getting everywhere I wanted to go. There are tons of ways to fill in open-jaws, but here are the ones we use:

• Land transit (bus, train, car rental, etc…)
• Discount Airliners – I use skyscanner.com in Europe, and AirAsia in Asia.
• Avios – BA Avios transfer from, like, everything, and start at 4,500 miles.
• Whatever miles you have – again, sometimes open-jaws are huge. You may be wanting to fill in with AA miles to get you across the world for the rest of your ticket.

Conclusions

I want to emphasize that there’s not really a wrong way to book your flight. If your only concern was to look at the Cheapest Miles To… posts and get the best price, you’re doing fine.

Stopovers are tools to help you get the ticket you want.

When people book multiple United tickets when they could have used a stopover… okay, that’s wrong.

But when people don’t use a stopover because they just want to go to one place, that’s totally cool. It’s a personal decision. So don’t try to book stopovers because you can. Book stopovers because you want to see more places.

And like I said, anything is possible. Even it’s only from mega-open-jaws that you have to fill in, your ticket is possible for less than you think.