It’s been fun looking back, reading my second trip report ever, written in December of 2013. That trip was my first time flying in international first class. Cathay Pacific from ORD to HKG was a mere 62,500 miles. One might say: How things have changed. Then again, we are about to embark on a trip around the world, adding the longest flight on Earth to our portfolio, and flying as a family of four in business class on both the A380 and 747 on the way home. All of this for mere pennies on the dollar, thanks to miles and points. So while, yes, getting to Southeast Asia has been a challenging affair, this seems to support, in Bon Jovi’s words: “the more things change the more they stay the same.” Let’s get into the details.

As always, we like to focus on pretty large trips for Spring Break. We’ve done everything from Cancun to Fiji. Choosing a destination is also fun, and sometimes flight and hotel availability dictate what is possible. There were two items that led us to choose Koh Samui. First, the Hyatt Regency opened there a few years ago and allowed 4 people to a room. Thailand has a 3-person fire code capacity, and many hotels can be difficult to book for a family of four. With ample availability during the dates we were looking to book, as well as an available standard suite that we could use a suite upgrade for, this seemed like a good use of points. Second, when The White Lotus announced they were filming in Koh Samui, we decided it might be time to revisit the island, especially if the show led to significantly increased tourism (if that’s even possible at this point). So we booked the hotel in the summer of 2024, and started to look at flights.

There was inventory for 4 in business class on Turkish Airlines, in both directions, when we started looking. The downside was that the layovers would require an overnight, but the arrival and departure times wouldn’t allow for a tour of Istanbul, a place NSPwife and I have never been, but would love to see. So we decided not to book, given this was the long way to Southeast Asia, and maybe a better connecting flight would allow for a day and night in Istanbul. That did not turn out to be a great decision. The Turkish inventory was gobbled up within 48 hours, and we were stuck without any good options. No problem, I thought. If there was inventory when I first searched, it’s bound to come back. And certainly a MSP > West Coast > SE Asia route would open up.

How wrong I was. I used Seats.aero and setup alerts for just about every North American airport to HKG, BKK, SIN, HKT, and KUL. I waited. And waited. And waited. Nothing. I began checking the usual suspects weekly (Alaskan, AA, Aeroplan, United, and Air France). Nothing. Then in November I got an alert that four tickets opened up with perfect times to get from MSP to BKK. Here was the unicorn! I logged in, got to the cart, and made a rookie mistake. I thought about it. I double checked everything. And 5-10 minutes later when I clicked checkout, someone else had grabbed the seats. What was I thinking?? Well, again, my thought was seats would continue to pop up. Again, a false hope. The rest of 2024 slipped by without a single option opening up. As January was coming to a close, we decided to open up our search criteria and started to look at options for the Seychelles, Caribbean, and Hawaii. Still, no specific luck with those destinations either.

Then in the middle of February, a flight opened up from Singapore to Chicago. Unfortunately it was by way of Frankfurt, Germany. So the “long way,” but had an intriguing setup: Flying in Singapore Business Class on an A380, and flying on Lufthansa Business Class on the upper deck of a 747. Sold. Plus, the overnight in Frankfurt might allow for a little bit more of a transition back to Central Time.

Then, amazingly, 24 hours later, a flight from Newark, New Jersey direct to Singapore opened up. THE LONGEST FLIGHT IN THE WORLD! Done and booked. So the long flights were set, and now the positioning flights were needed: Minneapolis to Newark, Singapore to Koh Samui, Koh Samui to Singapore, and Chicago to Minneapolis.

Minneapolis to Newark was pretty straight-forward, and we opted for a direct flight with Delta.

Koh Samui Airport is owned by Bangkok Airways and is really a monopoly in terms of flights. Thai Airways flies twice a day, and Scoot Airlines (owned by Singapore Airlines) also services the airport. So Bangkok Airways and Scoot were the only two options. And pricing reflected this! Our goal was simple though: Spend as much time as possible in Koh Samui, so flight times and not fares was what drove our booking decision.

Lastly, the flight from Chicago to Minneapolis was proving to be difficult, with three options: Have a 7-hour layover and spend 6,000 miles per person, have a 4-hour layover and spend 15,000 miles per person, or have a 2-hour layover and spend 50,000 miles per person. After a 39-hour “travel day,” the 7-hour layover was simply not an option. But spending 50,000 miles on an hour flight in economy vs. 87,500 to fly in Business Class from SE Asia to Chicago just seemed ludicrous. So we booked two different flights: We booked the United flight for 15,000 miles, and also booked the 6,000 mile flight on American, as my Executive Platinum status allows for confirmed same-day changes. And if there were still seats on the perfectly timed flight before we took off from Frankfurt, we would just try to make the same-day change and then cancel the United flight. Unfortunately, available space on American did not open up, so we were stuck with the the United Flight.

Per Person Airline Costs

• Positioning Flight #1: MSP > ORD. 14,400 miles + $5.60
• International Flight #1: EWR > SIN. 87,500 miles + $174.06
• Positioning Flight #2: SIN > USM. 18,750 miles + $67.11
• Positioning Flight #3: USM > SIN. 18,750 miles + $126.40
• International Flight #2: SIN > FRA > ORD. 87,500 miles + $56.20
• Positioning Flight #4: ORD > MSP. 15,000 miles + $5.60

Hotel Costs

• EWR Hotel: Renaissance: 1 Hotel Certificate (effectively $120)
• Singapore Changi Crowne Plaza: 2 Hotel Certificates (effectively $198)
• Hyatt Regency Koh Samui: 135,000 points
• Frankfurt Hotel: Hyatt Place – 2 Rooms, 1 Hotel Certificate + 5,000 points

A couple of additional items: We used our Ritz Carlton card $300 travel credit on the Scoot flights, and the Chase IHG credit card that gives me and NSPwife a free night each year has a $99 annual fee. So I’ve added $198 to account for the annual fees, but did not take out the $300 Ritz credit. Lastly, the American Express Bonvoy card, with its $120 annual fee, comes with an annual 35,000 point-certificate. The Renaissance Newark Airport hotel was 29,000 points, or $200, so a pretty good redemption for the certificate.

TOTAL Miles, Points, and Cash for 4: $2,057 + 1,102,600 Miles & Points

How would you value these trips? Well, let’s look at how much the long-haul flights and hotels would cost if paying in cash:

Flight Costs

Cash Price: Biz SIN > FRA (A380)

Cash Price: Biz FRA to ORD (747 Upper Deck)

Cash Price: Biz EWR > SIN (Longest Flight in the World)

Long-Haul Flight Costs totaled: ~$14,000 each.

Hotel Costs

Hotel Cash Price – Koh Samui

6-Night Stay in a Hyatt Regency Suite: ~$3,300

Ignoring the short-hop flights and shoulder hotel rooms, the core of the travel would have totaled nearly $60,000 without miles and points. Not a bad redemption!

One additional note. For this trip, I tried an app called Wanderlog to organize our itinerary, and I can’t recommend it enough. It was super easy to forward all emails from Airlines and Hotels so all confirmation numbers were in one handy place. When traveling to different time zones and taking flights that cross over different days, it was a great help to ensure my planning was accurate. It can also store places and activities that you find in the planning phases. I’ve tried these types of apps in the past, and never really found one that was user-friendly, or more valuable than just a nicely organized Google Calendar or even just checking email. But this checked all the boxes!

Now it is time to start the journey…