Bennett Bookings: How and Why I Scored Three First Class Tickets on the Same Trip

Bennett Bookings: How and Why I Scored Three First Class Tickets on the Same Trip


An upgrade-along-the-way approach is how I secure great deals I’d never get otherwise.

Hold on tight: This report is designed to expand your mind and get you out of your comfort zone.

My style of booking and flying is probably not like yours. There’s no accounting for taste. My goal here is to be provocative, not to convert you; hopefully it will trigger something that you can use for your own travel booking, even if only indirectly. Oh, and don’t worry if your head starts to spin a little, you’re going to get a window into my thought process.

A Mr. Upgrade Case Study:
First Class to Europe

Let’s say I’m planning a trip to the Balkans. Countries such as Albania, Bosnia, Kosovo, Montenegro, and North Macedonia. My preferred dates are about two months out, and there are no nonstops available. So, what am I to do?

Start with blue sky. Always start with blue sky.

Blue Sky Means First Class

Let’s begin.

If I didn’t mind taking the short transatlantic flight from New York to London where I would get minimal sleep and an average First Class seat I might have considered British Airways. But naaaah. One thing I hate about East Coast flights to London is that they’re so short, at less than seven hours in the air, so you’re guaranteed a poor night’s sleep (if you’re lucky). It’s the worst quality sleep on the planet and not a great way to start your trip.

Next up to consider is Lufthansa, but the only deal to be had with them is 14 days prior to departure, so that is ruled out unless I want to pay $8,000+. That said, my close-in upgrade strategy might come back into play 14 days prior to departure.

Air France and SWISS offer a First Class cabin, but they don’t have any strategies to get it at a very low price. So I don’t consider them because I want a deal for much less than the going rates of $10,000+.

That Leaves Emirates

Savvy travelers will know that Singapore Airlines is also an option, but hold that thought for a moment. I turn to Emirates because it’s one of my favorite First Class seats, as regular readers will know. But it’s often not considered on travel to Europe due to its Dubai hub. But I’m not overlooking it.

My first thought is that Emirates’ New York/Newark-Athens route puts me closer to my final destinations. Hate to disappoint you, but my first thoughts usually don’t last long. That grey matter needs some stirring before it’s cooked. But having a ticket in hand — an Emirates First Class ticket, at that — does take the pressure off.

Be Mindful of the Long Flight First

Now’s the time to point out that you should focus on your long flights more than the short flights. You want to optimize your comfort for the longest time you’ll be in the air; sounds obvious but most overlook this key detail. And to that point, I often decouple flights too, by booking the segments separately. Most travelers want the “protection” of all the segments on one ticket, so if there’s any schedule disruption, a single airline will have your back. But not me, if a great opportunity exists.

Call me lucky, but I generally don’t have a lot of problems when flying, so I don’t worry about late arrival misconnections. Plus, I typically don’t book tight connections to begin with because I’m happy to spend time in an airport lounge getting caught up with a good book or email. Tight connections are for plumbers, not travelers.

 Why Am I Trigger Happy When I Spot a Deal?

Some might call me impulsive, but hot deals often disappear as quickly as they come. It’s why I’m always telling you to book a hot deal the moment you see it, whether it’s via cash or miles. That’s because it gives you “insurance.” You can freeze opportunities if you are paying with cash, and free redeposit policies are generally the norm nowadays with miles.

While most people hold their breath and feel like they’re taking a plunge without a safety net when they make a booking, I do it 100% stress-free. So, if I see a deal, I lock it in. Every time. It takes the pressure off and I’m not concerned about getting all the details right the first time. More on that in a moment.

 Night Owl or Night Scowl?

New York/Newark-Athens is just over nine hours for a flight that departs at midnight on Emirates. I’m a night owl, so the last thing I want is the Delta and United flights that depart at 5:30 p.m. That’s a ticket for insomnia because I know I’m going to be awake most of the flight. No thanks. If you’re an early-to-bed person, perhaps you think differently, but your hotel room is likely not going to be ready for your early morning arrival anyway.

Plus, it seems like everybody forgets that the last thing you want to do is eat a big meal before you go to sleep. But what does everyone do on long night flights? Right! Nuts!

I like to eat before I board — I don’t fly for the food — and pop a melatonin right before I step on the plane to get some good shut-eye during the flight. Yeah, I know many of you like to indulge in Champagne onboard… but don’t forget, it doesn’t taste as good at high altitude (and you can get it on the ground).

Call me a snob to pass on the Champagne. Fine. But give me a Michelin-starred restaurant at my destination in a foreign land, and you have my attention.

Okay. So far, so good. Emirates, check. First Class, check. Late departure, check. My favorite New York airport, Newark, check. I book it using 85,000 miles that I transfer from Amex for the one-way flight, which otherwise goes for $11,479 (13.5 cents of value per mile), check. Ah, I almost forgot to say, this particular flight that was available with miles departed two days later than my ideal date, but that’s okay. I’m pretty flexible so it isn’t a big deal.

And Then a Nagging Thought

I’m almost happy it wasn’t better or I wouldn’t have thought to improve on it.

Improve on it, you say, Bennett?

Two minutes after that occurred to me, I remembered that the New York/JFK-Milan Emirates route offers the A380, the one with the shower.

How can you not take a Shower Flight? Taking a shower before you land and leaving the airport not feeling grimy is much more meaningful than it sounds — at least to me.

So, what do you think I did next? I booked the Milan flight one-way, my second booking of the evening. And I slept well that night with two Emirates First Class tickets to Europe in hand.

Yes, duplicate bookings can be detected and canceled automatically by the airline. So I took a chance, and Emirates didn’t cancel it for the month I held both tickets. (That said, United recently canceled one of my flights that was double booked, so keep in mind that this can be a risky approach.)

If possible, better to have two horses in a race than one.

My Upgrade Mindset

Move quickly. Process and book a flight that’s OK, then improve (aka upgrade) it later as more opportunities become available. Don’t try to be a perfectionist from the get-go. I looked at the available dates online and my perfect date was there, so I grabbed it. The Emirates flight to Milan on the A380 out of JFK was an improvement over the Emirates flight I had originally booked to Athens in some ways, so I secured it.

My Trade-Off Dilemma

So I had a dilemma: Take the longer Athens flight that offered more sleep out of Newark or the Milan flight that offered a shower out of JFK? If you have to choose between multiple flights, sleep on it and you’ll figure it out. Another dilemma was that there was more availability for connecting flights to the Balkans from Athens.

What did I do when I woke up the next morning? I checked for better routing.

It’s Always Upgrade Time

The next thing I did may have you scratching your head, considering that I had already booked two First Class Emirates flights. In my enthusiasm, I went back to the drawing board, because another option came to mind: Singapore Airlines. Ahhh, New York-Frankfurt… with Singapore’s new First Class suites. Dah.

You know what I’m always saying: People are most happy when they have a trip to look forward to. My thought is that people with a variety of options are twice as happy. So I booked the ticket on Singapore Airlines from New York to Frankfurt before the seat disappeared.

Yes, that’s right, on this night I went to bed with three First Class tickets, as it’s much better to have three horses in a race than one or two.

How Do I Get Such Lucky Tickets?

I make my own luck. Availability changes all the time and I don’t mind spending five minutes here and there in order to get a long flight that will make a huge difference to how my journey starts out, which ultimately sets the tone for the whole trip.


Which flight did I take? In the end, none of them. I had a family emergency that took priority so I deferred this trip. Am I disappointed? Only at having to postpone the trip. But I certainly don’t regret the effort because I’m now a mini expert on getting to Southeast Europe, which I plan to do in a couple of months. And that is so well worth it.

Also, you should know that I typically book three times more trips than I take for a variety of reasons. Opportunities are fluid.

This is exactly what I’ll do again when the time comes. When you’re a born traveler, as I suspect you are, it’s not a matter of if, it’s a matter of when.

See you up front.


100 Club
In January, I hit 100 countries visited. I’ve played with the idea of getting to every country over the years, but I wind up being lazy and returning to my favorites for the 7th or 12th time. But recently, the idea has come up again (just in case you were wondering about Bosnia and Kosovo). There was a nice little opportunity to pick off five with ease, so I figured what the heck. I love talking to locals and learning about their version of reality, which is often so different from what you read in the media. It’s just one of the countless reasons I love to travel. That reminds me, I need to join the Travelers’ Century Club.