Booked: Southeast Asia with a Touch of (First) Class

Trip booking with points is always an equally challenging and exciting process, almost as exciting for me as the trip itself. I recently locked down a trip to Asia with my girlfriend, which will be the first time visiting for either of us. 

It will also be the first time for either of us to fly in a First Class cabin! Read on to see what we’ve got in store, and also hear about a unique struggle I had when trying to book First Class with points.

Trip Overview

For this trip, we were both of the minds that anywhere in Southeast Asia would be exciting to visit, and wanted a mix of city experiences and relaxed island or coastline experiences. Fortunately nearly anywhere in Southeast Asia can provide just that mix, be it Vietnam, Malaysia, the Philippines, Thailand, and so on. 

We were able to construct an awesome itinerary incorporating both Singapore and Thailand, consisting of:

  • 3 nights in Singapore, Singapore
  • 5 nights in Koh Samui, Thailand
  • 5 nights in Chiang Mai, Thailand
  • 3 nights in Bangkok, Thailand

Read on to see the flights and hotels we booked to make this trip happen.


I booked the flights for this trip using points from a variety of sources, including one itinerary from New York (JFK) to Singapore (SIN) with Air Canada Aeroplan, and a return to Los Angeles (LAX) from Bangkok (BKK) using Cathay Asia Miles. Our connecting flights YEG-JFK and LAX-YEG were booked in economy class with Air Canada and WestJet.

Blue: JFK-IST-SIN on Turkish Airlines J class and Singapore Airlines J class via Air Canada Aeroplan; Yellow: BKK-HKG-LAX on Cathay Pacific F class via Cathay Asia Miles.

I was happy with the itinerary I was able to put together, especially given it was planned only 3-4 months out. As is common with booking award redemptions, I had to be open to departure and arrival cities in the continental USA. Living in landlocked Alberta also doesn’t help with constructing simple routings.

While not the most efficient flight path I could have envisioned, flying in business and first-class makes the journey very enjoyable, and it is exciting to be flying eastward on both legs, essentially circling the globe!

JFK-IST-SIN on Turkish Airlines and Singapore Airlines (Business Class)

I booked the flights out of North America first and actually happened upon them very early on in our trip planning process while browsing available business routings on Upon seeing a decent itinerary consisting of JFK-IST on Turkish Airlines business class, and IST-SIN on Singapore Airlines business class, both products I’ve longed to fly, I made a speculative booking. 

That booking, which ended up sticking, was purchased using Air Canada Aeroplan points, working out to 207,000 Aeroplan points + $168.60 in taxes, fees, and charges, total for two people. 

Of course, closer to departure and once we were locked into the trip, I called Aeroplan and downgraded the flight from Business (Flex) to Business (Lowest) to save 30,000 of my hard-earned Aeroplan points, a strategy you may have heard about from Jeff’s Changes to Aeroplan Flight Rewards article.

BKK-HKG on Cathay Pacific (Economy Class)

This was a simple short connecting flight from Bangkok to Hong Kong. For this flight, I booked economy class using some remaining Cathay Asia Miles which I’d converted from RBC Avion points

HKG-LAX on Cathay Pacific (First Class)

For our main segment back to North America, I’m excited to report that I managed to book Cathay First Class from HKG to LAX for 250,000 Asia Miles + 3,574 HKD in taxes and fees for two people. I acquired these points by combining points from a hodgepodge of programs, including Cathay acquired via RBC product switching, Amex Membership Rewards, and Citi ThankYou Points.

This will be my first time flying a true First class, so needless to say I am as excited for the end of the trip as I am for the beginning.

This booking had a few tribulations. Needing a way back to Canada from the Bangkok area, I had considered flying out of a number of hubs and airlines, whether it was Doha on Qatar, Japan on JAL or ANA, Taipei on EVA, etc. But I had little to no luck finding availability. I also considered Cathay Pacific, which had limited to no avails on partners like Avios. But I noticed that when searching via Asia Miles’ own website, there were much better avails.

Originally I looked at booking business class, but seeing First Class availability as well, I decided to just go all in. Knowing that transfers from Amex Membership Rewards and Citi ThankYou could take a few days to a week or more, I took a persistent approach to ensure I didn’t lose the flight during the transfer period.

I wrote about my experience booking Cathay First Class in a separate article: Booking Cathay Pacific Awards: Don’t Let Your Points Get Stranded! The TLDR is that I was able to put a 2-day hold on the ticket by calling Cathay, and then extend that hold by another 2 days continually by calling in on the day of the hold expiry. A bit tedious but worth it to ensure 250,000 points weren’t wasted.

After securing the booking, I was also able to figure out seat selection to get us into the two best seats on the plane: 1A and 2A. Interestingly, seat selection on the app wouldn’t allow me to change the assigned seats, nor did Cathay agents when calling in. But when I used the Cathay website I was able to make the selection.

Total Cost & Value

Especially when booking a complex business and first-class itinerary like this, it’s fun to think about the total money saved through using miles and points and the face value of these expensive flights. I tallied up the retail value in the table below using prices from Google Flights. All values are in Canadian dollars.  

FlightRouteClassPoints CostCash Cost Retail Value
TK 12JFK-ISTJ207,000 Aeroplan$168$11,545
SQ 391IST-SINJ$5,764
CX 700BKK-HKGY20,000 Asia Miles$145$500
CX 882HKG-LAXF250,000 Asia Miles$621$47,000 

While I would never personally consider paying in excess of $60,000 on flights for a trip, nor do I think a first-class flight is worth $47,000, this exercise still goes a long way in showing the outlandish value and experiences that can be derived from playing the miles and points game.


Hotel costs in Asia, particularly Thailand, are very inexpensive, and as a result, I was able to book an itinerary of almost exclusively luxury hotels using either free night certificates or reasonable cash rates. As usual, the preference was to stay at Marriott Bonvoy or Hilton properties to supplement the stay with complimentary breakfast, a perk of Marriott Bonvoy Platinum Elite status, and both Hilton Honors Gold and Hilton Honors Diamond statuses.


Singapore – The Singapore EDITION

As I was browsing through hotels in Singapore I came across the Singapore EDITION. The EDITION brand is known for being on the upper end of luxury and offering very local hotel experiences. I was impressed with my stay at the Reykjavik EDITION, so the Singapore EDITION caught my eye. 

The Singapore EDITION building is shared with the Boulevard 88 luxury condominium, located in the Upper Orchard Road shopping district.

The value proposition was also attractive. With a nightly rate of $900 SGD (~$900 CAD), but only costing around 50,000 points, I quickly jumped on redeeming two of my 50K Marriott Bonvoy Free Night Certificates earned from my Chase Marriott Bonvoy Boundless credit card

The hotel is also brand new, opening as of November 9, 2024. I am very much looking forward to my stay here and checking out the rooftop pool. Perhaps the only regret will be the lack of complimentary Marriott Bonvoy Platinum Elite breakfast.

Singapore – Conrad Singapore Orchard

With one more night to spend in Singapore, I chose to book the Conrad Singapore Orchard mostly for location and convenience: it is right down the block from the Singapore EDITION. I usually try to avoid hotel hopping, but I had a Free Night Award expiring in April, earned from my American Express Hilton Honors Aspire card, which I wanted to burn. 

Conrad Singapore Orchard, rebranded from the Regent Singapore

Nonetheless, Conrad is a solid and reliable Hilton brand so I look forward to the short stay here.


Koh Samui – Renaissance Koh Samui Resort & Spa

The Renaissance Koh Samui is located on the east side of the island, on a sort of mini-peninsula that juts out into the gulf. It is very near to Lamai Beach, which is allegedly one of the better beaches on Samui, providing a mix of relaxed vibes along with vibrant nightlife. 

While I had been eyeing up the Vana Belle Luxury Collection Resort, it worked out that I had 5 more Marriott Bonvoy Free Night Awards to burn by June and July 2024, so it made sense to use them up here. The nightly cash rate for the Renaissance was around 10,000 THB (~$400 CAD) so overall not a horrible redemption. Two of my certificates were 35K and the other three were 50K, so I made use of a small top-up of 39,000 Marriott Bonvoy points to make the booking.      

We were booked into the 1 King, Garden view, Balcony, Whirlpool room, but I have every intention to push for an upgrade to a villa and/or sea view room close to the check-in date and hope for the best.

Chiang Mai – The Kirin Farm

For something a little different and local, we are staying at a bed and breakfast called ‘the Kirin Farm’ on the day we arrive in Chiang Mai. This unique accommodation is situated on a hillside farm about one hour north of Chiang Mai city and features bi-level rooms with a balcony overlooking the mountains. Breakfast and locally sourced coffee are included.    

We stumbled upon this place randomly while scouting Google Maps. They had no website, just a Facebook page. They weren’t bookable on any booking websites but had great reviews on Google. I used Facebook Messenger to communicate with them and make the booking, which was only 2,000 THB for the base room, or 3,000 THB for the ‘Kirin View’ room which includes a bathtub (we opted for the latter).

To top it all off, there are pygmy goats all over the property for guests to pet and feed.      

As much as I like to enjoy the luxury side of travel, the prospect of a simple, quiet sunrise in rural Thailand at a place like Kirin Farm can be just as alluring.

Chaing Mai – Chiang Mai Marriott Hotel (formerly Le Méridien)

In Chiang Mai there isn’t much of a Marriott presence. Only the Chiang Mai Marriott Hotel. Fortunately, this hotel looked sufficient and centrally located for our needs, right next to the Old City.  

Photo credit:

The Chiang Mai Marriott Hotel is actually a very recent rebrand from a Le Meridien. I actually quite enjoy the Le Meridien brand but look forward to exploring the recently renovated property during our stay.

I made this booking using a corporate code to shave a small amount off the nightly rate, coming out to around 5,000 THB (~$200) per night.  

Bangkok – St. Regis Bangkok

Choosing a hotel in Bangkok was tricky, as there were so many affordable luxury options like The JW Marriott Bangkok, the Athanee Hotel (Luxury Collection), Conrad Bangkok, and so on. We ended up booking the St. Regis Bangkok for three nights with cash at an industry rate of 6,100 THB (~$230 CAD) per night.

The St. Regis Bangkok is a luxurious five-star hotel located in the heart of Bangkok, situated along Ratchadamri Road, one of the city’s prime locations. What really swayed us beyond the great location is the fact that the hotel is physically connected to the BTS Skytrain.

I look forward to the signature St. Regis Butler service and three mornings of fantastic breakfasts to start each day on the final stretch of the trip.

Total Cost & Value

HotelNightsPoints CostCash CostRetail Value
The Singapore EDITION250K certificates (x2)$0$1,800
Conrad Singapore Orchard1Hilton Aspire Free Night Award$0$400
Renaissance Koh Samui Resort & Spa55 certificates +  39,000 Marriott Bonvoy $0$2,000
The Kirin Farm1None$100$100
Chiang Mai Marriott Hotel4Corporate rate$800$1,000
St. Regis Bangkok3Travel agent rate$700$900

Through the power of miles and points, over $4,600 CAD in hotel costs were saved!


It’s great to have gotten everything in place for my first trip to Asia, and I am looking forward to escaping the cold Alberta winter to enjoy new food, hotel, and cultural experiences along with ample relaxation. 

Keep an eye out for my reviews of the aforementioned business and first-class flights and luxury hotels in 2024!

Reed Sutton

Reed Sutton

Founder at Frugal Flyer
Reed is addicted to the art of earning and redeeming travel points, and frequently pairs his trips with his other hobby: photography. Through Frugal Flyer, Reed aims to distill some of the complex and esoteric points strategies into digestible information. Furthermore, he hopes to use his technical expertise to develop invaluable applications and tools for the travel community.


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