Let’s walk through Secret Trip 2.0 in more detail, breaking it down to show just how to book award travel for those who might be hesitant.

Planning a multi-week, multi-destination award trip might sound overwhelming at first. And to be honest, it can absolutely be a hassle. Changing award flight availability happens all the time on high-demand routes. It can be tense waiting for points to post because you just don’t know if someone else out there has similar thoughts as you.

So, let’s break this down into simple steps you can use to book your own travel. We’ll use Secret Trip 2.0 as our guide. If you can follow along for this one, planning will be easy.

Preliminary questions you need to ask yourself before starting

There are a few questions you’ll want to ask yourself before you start planning your own trip. This includes things like:

• Where do you want to go?
• What points and miles do you have?
• Are you comfortable flying through other international gateways?
• Do you have a backup plan?

We talk about all of this and more in our primer on how to book award travel. If you need a refresher or want to learn, we suggest you start there first.

Using Secret Trip 2.0 as a case study on best practices and what to avoid

Let’s dive into this for this trip. We’re going to start with three key destinations:

• Melbourne, Australia
• Bali, Indonesia
• Kuala Lumpur, Malaysia

I originally wanted to replace Bali with Fiji, but ran into issues booking it (hence the backup plan!) and had to pivot. Coming in from Los Angeles, I needed to handle some business first with just getting down there.

The flight home actually came first

The rule of thumb is that the longer the flight, the harder it is to find awards. Thus, I wanted to focus first on the flights across the Pacific. I got lucky because I knew a new route was eventually going to become bookable for China Airlines flying to Phoenix, Arizona. That’s close enough to make it work.

On July 25, 2025, I found and booked two seats in China Airlines business class on the TPE-PHX route for travel on June 24, 2026. Sadly, as much as I tried, I just could not get four seats to appear, so two seats would have to work for now. I booked these seats with Flying Blue using the Air France app for 72,500 miles per person.

Three days later, on July 28, 2025, I decided to mess around on the Flying Blue app. I kept refreshing the Air France app search results multiple times, for dates that are +/- 1 day from the date I already booked. With two more seats to book, I needed to get the rest of us home. Despite the search results showing nothing, I kept refreshing. You know what they say about the definition of ‘insanity’, right? Well, believe it or not, but the other two seats appeared, and on that same flight for the same day and the same price. Score!

Against my own advice, Australia to Bali came next

I normally book the transoceanic flight first. But since I knew I would be booking upgrade space to Australia rather than award space, and upgrade space was plentiful, I wasn’t that concerned. Thus, I locked myself in on the flight from Melbourne, Australia to Bali.

There’s a good reason why I did it–I was worried the price was too good for the route. It was only 28,000 Flying Blue miles per person to fly in business class. Are you kidding me? I would take that price all day long. On July 29, 2025, I booked Garuda Indonesia business class MEL-DPS for travel on June 17, 2026.

If I had to cancel it at some point and change plans, it’s not the worst thing to pay the award cancel fee with Air France. Now, I just needed to make sure I made it over to Melbourne.

Expiring miles got me stuck

No one likes miles that are going to imminently expire. I needed to extent the bulk of my Singapore Airlines KrisFlyer miles for one year, but everyone only gets one extension with Singapore. So, I knew I needed to fly Singapore for the most efficient use of those miles.

The good news is that flights wholly within SE Asia are pretty cheap (21,000 Singapore KrisFlyer miles per person in business class). And the flights were readily available as awards when booking so far out. With an entry date to Bali set in stone, it was simple enough to book a flight from Bali to Kuala Lumpur. And if miles are expiring, I better get this thing locked up before someone else takes it.

On July 29, 2025, I booked Singapore Airlines business class DPS-SIN-KUL for travel on June 20, 2026.

The first flight was one of the last booked

With the China Airlines flight in hand, I sat on the flights to Australia. Sure, I booked placeholder flights on airlines where I could get free cancelations on awards. And I played the ‘fishing for a cheap cash upgrade’ game but didn’t expect it to work.

I needed to requalify for Delta Diamond Medallion status first. At the time, I was only a few thousand MQD away from doing so. Thankfully, if your goal is to earn status via credit cards, you don’t need to wait for the credit card statement to close to earn Delta MQD. I could just make a large tax payment and earn the missing MQD. And that’s exactly what I did. With the Diamond Medallion status, I gained the ability to choose 4 global upgrade certificates (GUCs) that allowed me entry into Delta One by booking Premium Select.

While I didn’t sweat on finding an award seat, I did sweat on finding upgrade space. Delta only releases some seats bookable by these GUCs. And when the flights first became bookable, the upgrade space was there. Then it disappeared for a couple of weeks. No one actually booked the flights–the seat map showed no one was sitting there. Delta just decided it wasn’t available. Eventually, the Los Angeles to Sydney flight opened up but the flight to Melbourne never did.

So, on September 14, 2025, I booked what I could. The tickets instantly cleared into Delta One and I was out 148,700 SkyMiles per person, the price of booking Premium Select. No one said business class was cheap, but upgrade space is easier to find than true award space. Delta One awards would have cost 335,700 SkyMiles per person if I didn’t use the upgrade.

Of course, joke’s on me for buying Premium Select as a starting point. Our flight departed with 6 empty seats in Delta One. Presumably, that means I probably could have purchased economy class (39,100 miles/person) and still received an upgrade into Delta One on the day of travel. Hindsight is always 20/20, and I’m not sure I would have changed my approach on this particular journey.

One last thing, I booked a backup itinerary if this ultimately didn’t work. Delta also started flying to Hong Kong. Thus, if Australia upgrade space didn’t appear, I was prepared to go to Hong Kong by booking award flights that transited Vietnam. Again, not ideal to have so many connections, but sometimes you need a backup plan. I just held off on the flight to Hong Kong until I knew for sure what I could upgrade.

Now that I knew I was heading to Sydney, I could book Sydney to Melbourne

I will admit I sat on the rest of this for quite some time. To be frank, I didn’t like the award options I was seeing. I found lights on Qantas in business class for just 12,500 Avios but only on June 13. That would be the same day we arrived. Could I convince everyone to sit around at the airport for about 5-6 hours and then fly to Melbourne without a chance to explore Sydney? If it were just Jenn and I, that might be an option. But with the kids with us? I think that’s too cruel.

With that option out the window, I didn’t find Qantas awards bookable with British Airways Avios for June 14. I found June 15, but that doesn’t give much time in Melbourne, the intended destination. Hence why I just sat on it. I monitored cash prices and award flights. Awards didn’t open up, but cash flights got cheaper.

And so, on January 11, 2026, I booked us in Virgin Australia business class SYD-MEL for travel on June 14, 2026. The price for business class wasn’t ideal, but $400 (in USD) in business class was the cheapest I found for my date. In terms of ‘deals’, this might be the worst one, but if I had more flexibility, I could have purchased the Qantas fare via British Airways. If only!

You could partially blame this one on a lack of planning, but it’s more a general lack of flexibility. I wish I could have flown to Australia earlier to spend more time there but obligations kept us in town.

That pesky flight to Taiwan was a real self-induced problem

Here is where I admit my problem–I booked and then re-booked and then re-booked the flight out of Kuala Lumpur. In the end, I spent too much time, effort, and money on this flight. It all worked out, but this was the dumbest sequence of events.

I had more Singapore KrisFlyer miles that were going to expire, so I naturally thought maybe it makes sense to use them up on this journey. It’s much more expensive than the Bali route, coming in at 50,000 miles per person for Business Advantage. That’s because the Business Saver rate of 34,000 miles just didn’t exist and I wasn’t going to depend on the waitlist. And, just because we’re reveling in the wrong moves I made, I also needed to top off my account with just a few thousand more miles to do this. But it’s done, right?

Naturally, I walked away from this thinking “what a waste” because though I could add in a free stopover in Singapore for booking Business Advantage, I had no time to do it. I wasn’t about to sacrifice time I could spend in Kuala Lumpur for time in Singapore. It was simple enough to just book AirAsia X or Malaysia Airlines and canceled the flight. (I would later use my Singapore miles for future travel unrelated to Secret Trip 2.0.)

So, I booked AirAsia X, finding a cheap flight to go up to Taipei. I even got reimbursement of the ticket price from the $300 travel credit on my Ritz Carlton card. You’re not supposed to be able to reimburse the cost of tickets, but sometimes you can get away with calling it a seat fee. Anyways, I ended up psyching myself out with this. Word on the street is that AirAsia X out of Malaysia especially is very concerned with middle names showing up on tickets. And when I booked, it just asked for a first and last name, I didn’t realize the middle name was supposed to be included in the first name.

I read mixed experiences about this. Some said to contact customer service, but sadly all customer service is funneled through a bot on their site. This bot doesn’t allow for name changes and, as AirAsia is a low cost carrier, all fares are non-refundable. So, I just left the ticket alone and booked something else. Normally middle names don’t spook me, but here I didn’t want to run any risk of a denied boarding when I absolutely needed to be in Taiwan.

Next up, I found award flights on Malaysia Airlines in economy via Air France. That’s a weird combination: a oneworld member airline bookable with SkyTeam miles. The price they wanted was 43,750 miles for the four of us + $247.60. That beats Singapore for 50,000 miles per person, though there’s a big fuel surcharge to pay for economy. Still, I thought it was good enough, so I booked it.

But after booking, I couldn’t easily view my tickets anywhere online. I could have spent time on the phone, but I’ll be honest and admit I didn’t have the time for that. And I’ve been in this scenario before where I couldn’t see the reservation online but it worked out when checking in. Against all logic, I canceled once again. Of all my faults, this one is perhaps the biggest one that’s on me. I was just extremely risk-adverse with this one after all the cancels.

Satisfied with the routing, I booked the same Malaysia Airlines flight with cash just days before we left for Australia. I paid $300/ticket, with included luggage and seat selection in the fare. That doesn’t include the cancel fees I had from Singapore or Flying Blue, or the fare from AirAsia X that was covered by the travel credit I had no other use for.

In retrospect, this is a series of mistakes that I did to myself. I probably could have left extra time at the airport for AirAsia X to correct the missing middle name. And Flying Blue award flight might have worked, but we were getting set to fly out on the trip and didn’t want to deal with that in the middle of it. I’m not perfect, but hopefully this helps you learn from my mistakes.

The best part about making mistakes with award flights is that they’re generally fully cancelable as long as you pay a (usually reasonable) fee.

Hotels were easy to book on this trip

Since I was using hotel credits that I had from credit cards and they reset on January 1, I booked some hotels in 2025 and some in 2026. As some hotels were booked with cash, I double-checked the pricing roughly once a month or so to see if prices changed. You have to be careful if you’re canceling and rebooking if on award rates because the nights might not go back into award inventory. It’s less of a concern for cash bookings, but it’s important that you book refundable rates before you try rebooking.

Once I had dates for each city based on the flights booked, I worked on the potential hotel for that city. I prioritized hotels based on:

1. Location, hopefully close to public transit or near the city center
2. A large enough room for us to all be in the same room, which isn’t a guarantee in every city
3. Elite status benefits, or an alternative that would ideally give free breakfast to make things easy for us
4. Cost, because no one wants to take out a second mortgage for staying at a hotel

If I were staying somewhere with limited hotel inventory or where the stay is solely dependent on the hotel (like in The Maldives), I might have booked the hotel first before the flights. However, for this trip, booking the hotels after the flights was the recommended order.

Booking tours when Viator or Tripadvisor had bonuses

I’ve chatted before about the Capital One shopping portals. Every so often, which feels like once a month, the portals run a bonus promotion for things booked on travel sites like Viator or Tripadvisor. We took a few tours over the course of Secret Trip 2.0, and so why not earn a few extra miles doing so? I waited until the bonuses reached at least 30X for these companies and then booked my tours.

Thus, a tour that would cost $200 at least additionally earns me 6,000 Capital One miles. Even if you view the miles as 1 cent each, it reduces the price of the tour down to $140, which is great. But it’s in this way that I can help restock my Capital One miles. It can be a little tough otherwise to amass large sums of Capital One miles.

If nothing else, it’s a nice little bonus for booking a tour I would have booked anyways.

Hope this helps for your own planning and don’t worry too much about making mistakes. We all do!