Is now the time for complex or aspirational bookings? My recent experience says no

When people were staying at home and not traveling over the past two years, we grew mountains of points and miles. Now that borders are reopening, you might want to get out there and use your stash of points. Plus, I never believe in hoarding points, since devaluations can occur at any time.

On the flip side, travel is a mess right now. Just look at what's happening at European airports and the number of flights being canceled and delayed on a regular basis. And this doesn't even take the baggage issues into account.

All of this raises a question: You've got a ton of points and miles stacked up, ready for an aspirational booking, but is now a good time for these complex trips? According to my recent experience, I say no.

Let's look at all of the headaches I dealt with on a recent around-the-world ticket and why I don't think now is a good time for complex, aspirational flight bookings like this.

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You can't book these awards online, and hold times are atrocious right now

Many aspirational bookings like around-the-world awards, some partner awards like redeeming Virgin Atlantic points for ANA first class and other complex itineraries cannot be booked online. You'll need to call to make these bookings.

Due to ongoing issues with air travel, it's not easy to reach customer service quickly these days. You may wait on hold for several hours before an agent answers, and what if that person needs to transfer you to another department? I went through this multiple times with Asia Miles when booking, rebooking and dealing with flight cancellations leading up to my recent trip.

If you can book your aspirational flight online, fantastic. You can book Singapore Airlines' first-class suites and Lufthansa first class online, for example. However, more complex routings and certain partner awards require a phone call, and calling customer service is not a quick event right now.

Related: How to quickly reach an airline customer service agent

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Complex routes with more flights mean more chances for problems to occur

If airlines are having trouble flying you from point A to point B right now, just imagine how many problems might pop up when you cross multiple borders in an itinerary involving a dozen flights and a handful of different airlines. Remember, border restrictions related to the pandemic are not totally gone — they can still change in the middle of your trip, in fact.

Look at what happened to me, just days before I was supposed to depart. An Asia Miles representative called to tell me that all flights between Tokyo and Seoul, South Korea, had been canceled by Japan Airlines for the foreseeable future.

After researching my options, I removed South Korea from my itinerary and decided to go to Ho Chi Minh City, Vietnam, instead. However, while waiting for JAL to confirm my new flight, the last seat in business class disappeared. After several rounds of attempting to rebook, I didn't get a confirmed flight until the day before my scheduled departure from Los Angeles International Airport (LAX). Talk about stressful.

Later during my trip, when trying to check in for a flight online, I received the following notification from Qatar Airways: "Due to a no-show, this reservation has been canceled."

I didn't have any no-show flights on my around-the-world reservation, and thinking my ticket had been canceled — thus stranding me on the other side of the world with no flight to get home — was panic-inducing. After a long wait on hold, an agent reviewed my ticket and informed me this was simply a computer error. My ticket was still intact.

Moral of the story: The more flights you have in your reservation, the more opportunities there are for problems to occur.

Related: How I booked an around-the-world ticket in business class for 170,000 miles

If and when problems occur, dealing with customer service isn't easy

If you're flying on a complex trip with multiple flights involved — such as the United Excursionist perk or a multicity ticket with stopovers and open jaws — let's assume there will be at least one bump in the road. What will you do?

If it's a delay while you're at the airport, the operating airline should be able to handle it. If it's anything more complex, you'll likely have to call the award program you booked your ticket with. This brings you back to the problem of long hold times, limited award seat availability and waiting for your seats to be confirmed while other passengers who booked directly with the airline are likely snapping them up faster than your phone agent can confirm partner award space.

Customer service is a thankless job, and it's a mess right now. Everything I've said depends on the ability to reach a customer service agent, which isn't guaranteed to happen in a timely manner. Chat services exist, but wait times can be extensive too.

I say all of that to say this: The more complex your itinerary is, the more chances you have for needing to contact customer service with an issue. Take this into account if you're planning to book a complex, aspirational trip with your points and miles in the near future.

Related: Is Twitter quicker? Best ways to use social media for travel customer service

Changes can happen, and the seat you really wanted might not be available

The day I flew home, I was supposed to fly Qatar's Qsuite on the A350-1000 from Hamad International Airport (DOH) in Doha, Qatar. Qatar Airways had two flights scheduled. My flight (the first) was canceled, and I was offered a move onto the later flight, departing three hours later that same morning.

The problem: There were no more seats available in business class. Nor were there any business-class seats available for the next two days. I could either fly home in economy on my original date or wait three days to fly in business class. Spending 16 hours in economy — when I had paid the required miles for business class all the way around the world — and not getting a partial refund or compensation for it wasn't very fun.

Additionally, an aircraft swap on my flight to Ho Chi Minh City went from a lie-flat seat to an angle-flat seat. Since it was a flight departing at 1 a.m. and lasting 6 1/2 hours, I'd planned to sleep. An angled business-class seat isn't the end of the world, but it was less comfortable than expected.

The same concept applies to several emails we've received from frustrated readers recently. When you've booked a particular seat that you want to fly on a particular aircraft type with a particular airline, what happens if your flight is canceled or there's an aircraft swap? Seats in premium cabins are limited — sometimes to just four to eight seats, if you're booked in first class. A canceled flight might put you into a situation where all of those seats are occupied on the next flight. Do you choose to take the first available flight — which isn't in the seat type you wanted — or alter your vacation by several days while waiting for your desired seat?

Related: Check your airline ticket after booking to make sure you weren't downgraded

Asia Miles has a very small team that can handle changes to award itineraries

You may hear "push three for changes to award bookings using Asia Miles," but that doesn't mean the person who answers the phone will be able to help you. That was the lesson I learned over the past few months.

After needing to change my flight dates due to being sick earlier this year, calling to deal with the canceled JAL flight and also the question about my possibly canceled itinerary, I learned that only a handful of people in Hong Kong can issue around-the-world tickets or make changes to partner awards with Asia Miles.

You also can't contact this team directly — even if you call the Hong Kong phone number on Asia Miles' website. And since this team is across an ocean, they tended to call me back at 2 a.m. my time, creating numerous rounds of phone tag.

The lesson here is that you may think your waiting period has ended once an agent finally answers the phone, but that might not be the case. When specialized teams are involved in changes to award tickets or complex itineraries, you may spend even more time getting bounced around on the phone or waiting for callbacks that come at inconvenient times.

Related: 7 tips to avoid getting stranded by airlines when things go wrong

Bottom line

I'm really glad I flew an around-the-world itinerary. I never could've afforded a business-class itinerary like this if paying cash. Instead of $11,000, I spent 185,000 miles and $1,000. And I was able to see several countries I'd never been to before that aren't very close to one another.

However, the frustrations along the way were many. The stress caused by these issues left me wondering if I would actually take my trip, whether I would make it home and if I was enjoying the trip despite these and many other stressors along the way.

After two years of travel restrictions due to COVID-19, you may be sitting on a mountain of points and miles. If you're like me, you're keen to book aspirational and complex itineraries before the next devaluation comes along. However, my experience tells me that right now is not the time for ultra-complex bookings. The chances for headaches are many, and it takes the fun out of travel. So for now, I'll be waiting for things to smooth out before I book any more complex trips. Until then, simple trips from point A to point B are in my foreseeable future.