After leaving the kids at home and visiting Cuba, and later French Polynesia, we convinced ourselves that what we really needed next was a quiet, snowy cabin in the middle of nowhere. No more sweaty nights. No more dirty streets. Just cold air, silence, silence, and maybe a fireplace.
That plan lasted about five minutes. Instead, we are back to doing what we do best and planning a trip to Thailand with miles and points. Because apparently we learn nothing, and also because Thailand has been calling our name for years.
If you have ever looked at flights to Asia and thought “there is no chance I am paying that,” this is exactly how we planned this trip without doing anything fancy.
The Destination
We had every intention of sticking with our plan. Havana is hot, dirty, and adventurous. French Polynesia is hot, beautiful, and rugged. We loved both trips, but after each kid free trip, we found ourselves craving cold and cozy. In reality, it took about half a second to decide we should go to Asia instead. It is hard to pass up the chance to go somewhere big and new when you are planning a trip without kids.
Asia is not exactly a small region, so that required some narrowing down. I started by looking at nonstop and one stop options from the US. If this is going to be a shorter trip, we need direct ish flights that do not eat up two full days of travel. Using FlightConnections and filtering to SFO, I narrowed down a few realistic destinations and then looked at which airlines actually fly those routes. This matters because we wanted to fly business class, and I needed to know which miles and points I could use or still needed to earn.
Quick note for anyone not chasing fancy seats. These exact same steps still work if you are paying cash or flying economy. We did this with Japan and Argentina. Do not bail on learning this stuff just because you think it does not apply to you. Business and first class require more flexibility and patience, but the principles are the same, and this is all doable for normal people.
All of that is just context and transparency, because I ended up scrapping that method and going backwards. Part of our recovery from hot and rugged travel is that we wanted real urban comfort. We were ready for AC, good food, and a little bit of luxury, but we could not fully give up on some level of adventure. After a bit of research, Thailand kept rising to the top, so I dropped the pin on Bangkok and worked backwards from there.
Planning Thailand with Miles & Points
From there, I filtered through potential layover cities to figure out which airport would give us the best routing and the best miles and points value. Tokyo, Singapore, Hong Kong, and Vancouver were the main contenders.
I went straight to Vancouver first with Air Canada Aeroplan. That nonstop was very tempting, but good award availability was basically limited to one seat or awkward routings through Delhi on Air India. Not exactly the romantic getaway vibe we were aiming for. Award space gets scooped up fast, and many programs, including Aeroplan, do not always have access to partner airline seats until after their own members have already grabbed them.
I already knew the main players for the other hubs. Tokyo meant ANA or Japan Airlines. Singapore meant Singapore Airlines. Hong Kong meant Cathay Pacific. From there, it was just a matter of checking award charts, confirming what the pricing should be, and then seeing what was actually available in the real world.
Airline Award Bookings
Each airline handles award pricing differently, but the easiest way to get the ball rolling is honestly just to start with Google. Something as simple as searching “Singapore Airlines award chart” will usually point you in the right direction. Not every airline publishes a true chart anymore, but most have some method of showing how many miles or points you will need. Some programs use dynamic pricing that moves with cash prices, while others still have fixed ranges.
After checking the chart or award calculator, I move straight to the airline’s booking platform and search as far out as the calendar will allow. Business class sells out fast, so looking at the very end of the schedule gives you the best sense of what is realistically available. When I did this with Singapore Airlines, I could see the 117,000 mile pricing, but most of the seats were already waitlisted. Nearly a full year out and the good stuff was already getting grabbed. I made a mental note of that.
Japan Airlines has a semi fixed chart. Flights to Japan start around 55,000 miles, with an additional 40,000 miles to continue on to Thailand. At the time of my initial search, transfers from Capital One to JAL’s program were at a 1000 to 750 ratio. That meant the 95,000 miles needed for the booking would actually cost about 126,000 Capital One miles. That was a tough pill to swallow. A week or two later, they announced a transfer bonus that brought the ratio up to 1000 to 975, dropping the real cost to around 97,500 Capital One miles. Much more reasonable, and a good reminder that timing matters with transfers.
Cathay Pacific was refreshingly simple. Their award chart is easy to understand, with pricing around 88,000 miles to Hong Kong or 115,000 miles all the way through to Thailand. Even better, there was decent award space available at the end of the calendar, which is always a good sign.
Then there is ANA. On paper, it is the cheapest option by far at around 68,500 points for business class. In reality, it is also one of the hardest seats to actually book. It is a great product at a ridiculous price, so the award space disappears almost instantly. Every time I checked, it felt like I was racing the entire internet for the same two seats.
After weighing all of this, I started narrowing things down and focusing more seriously on Cathay Pacific as the most realistic option for us with JAL as a great potential for the return.
Quick reality check: this takes flexibility. Award space changes, flights disappear, and sometimes the perfect plan does not exist for your exact dates. If you are locked into specific days, this gets harder. Not impossible, just harder.
The Booking
Transferring miles and points sounds intimidating, and I know it scares a lot of people off, but the actual process is pretty streamlined. You figure out your plan, confirm availability, transfer from your credit card program, and book the flight. There are nuances and quirks with every airline, but that is the basic flow. Each program transfers to different partners, so you just find the redemption page, look for the transfer to partner option, and follow the steps.
From first search to booking, this probably took me a few nights of casual research while half watching Netflix. I have a little mor practice, but it doesn’t have to be an overwhelming and time consuming monster.
One important rule if you are new to this: never transfer points until you see the exact flight you want available. Transfers are one way and you cannot undo them.
Once I had the flights mapped out, I transferred points from Amex for Cathay Pacific and from Capital One for Japan Airlines. I waited a few days for the specific dates and flights we wanted to open up, then booked everything as soon as the availability popped.
Instead of booking the full 115,000 miles all the way through to Thailand via Hong Kong, I decided to save the points and book 88,000 miles from San Fransisco to Hong Kong. That actually worked out better for us anyway, since we are spending Chinese New Year in Hong Kong and then catching a cheap forty dollar flight to Thailand the next day. Sometimes the “less optimal” award route ends up being the better real world travel plan.
On the way back, I went with Japan Airlines because there was direct availability out of Bangkok, a short and easy layover in Japan, and a perfectly timed flight back to Seattle that gets us home the same morning. The transfer bonus definitely nudged that decision along, but the routing itself was just clean and painless, which matters more than people like to admit.
Wrap Up
I do not share this stuff to flex. Okay, maybe a tiny bit. But mostly, I write posts like this to show that the miles and points world is not some exclusive club for finance bros and spreadsheet addicts. It is just a skill, and like any skill, it gets easier the more you use it.
We are flying to Hong Kong and Thailand in lie flat business class seats for a total of 376,000 points plus about $900 in taxes and fees. Yes, that is a lot of points. But with a little prep work, some patience, and a willingness to learn the basics, anyone can put together the same kind of trip when planning a trip to Thailand with miles and points.
And you do not have to go full business class to make this worthwhile. Even premium economy would cut that points total dramatically, and standard economy drops it even further. The point is not the seat. The point is opening up trips that would normally feel out of reach and realizing that the world is way more accessible than it looks from your couch.
If you have been sitting on points and waiting for the “perfect” redemption, this is your sign to stop waiting and start booking.
Key Take-Aways
Japan Airlines business class is one of those redemptions I knew about, but had kind of forgotten how good the pricing actually is. At around 55,000 miles each way to Japan, it is still a fantastic deal. Yes, the transfer ratio from Capital One is not always ideal, but even at roughly 74,000 Capital One miles for a lie flat business class seat to Japan, that is a pretty slick redemption. The Venture X often comes with a 100,000 point signup bonus, which means with some normal spending and a little patience, you could realistically earn enough points to fly you and your partner to Japan in business class.
Cathay Pacific also offers surprisingly affordable economy awards to Hong Kong, often around 27,000 points one way. It is a long flight, but that same Venture X card could realistically cover round trip economy flights for you and your partner if you plan it right. That kind of redemption alone can be the difference between a trip feeling “maybe someday” and feeling actually doable.