We just got back from 16 days in Singapore and Thailand with our two kids and I honestly cannot stop thinking about it.
People ask me all the time “Hilda, what is the end-to-end process like when you are booking a big family vacation? How do you find the flights? How do you plan the hotels? How do you make all the pieces fit together?”
So I decided to write this post as the most detailed breakdown I have ever shared, because I want you to be able to follow this exact same process for your own family.
I am going to walk you through every single thing. The research. The cards we opened. The tools we used. The moments that made us laugh and cry and hold each other a little tighter. And yes, the numbers, because I think you deserve to know exactly what a trip like this actually costs when you do it the right way.
This trip had a cash value of $52,357. We paid $1,787.72 out of pocket for a family of four for 16 days across four cities on two continents. Everything else was covered by points and miles we had been quietly earning from our everyday spending over the past five years.
One important note before we get into it. That $1,787.72 does not include activities, food, shopping, or local transportation. We paid for all of those with credit cards to earn even more points while we traveled.
For every foreign transaction on this trip we used our Alaska Atmos Summit card which earns 3x on all foreign purchases.
Alaska Atmos Summit card
Okay. Let me take you back to the beginning.
How It All Started: Finding the Flights
The first thing I always tell people when they ask how I plan a big trip is this. You do not plan the itinerary first. You find the flights first and let the availability shape everything else.
I search one-way flights rather than round trips for this exact reason. When you search one way, you have the flexibility to fly one airline going and a completely different airline coming back, which means you can find the best deal in each direction independently.
That is exactly what we did on this trip and it saved us a significant amount of points compared to locking into one round-trip program.
I knew immediately that going to Southeast Asia I wanted to look at Singapore Airlines, Qatar, and Emirates. Emirates came off the list quickly because their taxes and fees are high and I did not want that eating into our budget.
Singapore Airlines was at the top because I had flown them twice before and absolutely loved the experience, and I knew I wanted my kids to experience it too.
Getting to San Francisco: Southwest and the Companion Pass
Our trip technically started in Baltimore, not San Francisco. The Singapore Airlines deal I found was departing out of SFO and not our home airport, so we needed a positioning flight to get there first.
This is something I always encourage families to consider, and be willing to position to catch a better deal. Sometimes the best redemptions are not out of your home city and a short domestic hop is absolutely worth it.
We flew Southwest from Baltimore to San Francisco for this. And here is where the first win of the trip happened. Both my husband and I hold the Southwest Companion Pass, which means our two kids flew completely free on our tickets.
Four people traveling. Two paid fares. This is why I talk about the Companion Pass so often, it is one of the most consistently valuable travel tools for families.
How to Earn the Southwest Companion Pass post
We stayed overnight at the Hyatt Regency San Francisco Airport, which has a 24-hour shuttle from the terminal and is perfect for a layover before a big international departure.
San Francisco to Singapore: Singapore Airlines Business Class
Points used: 428,000 Amex Membership Rewards transferred to Singapore Airlines KrisFlyer.
Taxes paid: $22.40 for all four passengers.
Cash price: $26,000
This is the redemption I am most proud of from this entire trip and the one I want to walk through in the most detail.
I started searching nine months in advance. Finding business class availability for four passengers on the same flight is genuinely hard and the earlier you start the better your chances. I always recommend starting nine to twelve months out for a trip like this.
When I began my search I checked every airport Singapore Airlines flies out of in the US: Seattle, New York, Newark, Los Angeles, and San Francisco, just to find where availability existed.
After searching I found saver fares at 107,000 KrisFlyer miles per person in business class. For four of us that meant I needed 428,000 miles total.
Now here is where the planning really started.
Before I even thought about transferring points I had to make sure I actually had enough to cover this redemption. I had opened the Amex Business Platinum and the Amex Business Gold specifically to build up a large Amex Membership Rewards balance.
Between both welcome offers and ongoing spending we had earned close to 400,000 Amex points between the two cards, and I had additional points already sitting in my Amex account. Together I had enough to cover the full 428,000 needed.
Once I confirmed I had enough points I went back and checked the availability again. The four seats were still there. This is the moment things get real.
Before I transferred anything I added my husband and both kids as nominees on my Singapore Airlines account. Singapore requires you to add all passengers as nominees before you can book award flights for them. This is a step that a lot of people miss and it is a step you cannot skip.
Then came the transfer. I moved 428,000 Amex Membership Rewards points to my Singapore Airlines KrisFlyer account. Amex transfers to Singapore Airlines at a 1:1 ratio and the transfer was instant. The moment those 428,000 KrisFlyer miles landed in my account I went straight back to confirm the booking.
I have to be honest with you about how I felt at that moment. Transferring points is permanent. Once your points leave the bank they cannot be transferred back.
If those four seats had disappeared between the time I transferred and the time I tried to book, those miles would have been stuck in my Singapore Airlines account. I could still use them but they would be limited to Singapore Airlines and Star Alliance redemptions only. My heart was racing the entire time.
But I had done my homework. The availability was there. I booked all four seats and the taxes came to $22.40 for our entire family of four on a 17-hour nonstop business class flight.
I cried. I am not going to pretend I did not.
The cards that made this flight possible:
The Business Class Surprise
I told the kids we were flying economy.
Completely straight face. I said business class was just too expensive and we would be in the back of the plane. My daughter accepted this without question.
My son looked at me for a long moment, said okay, and then proceeded to ask me every few minutes whether we were really flying economy. Every time I said yes, baby, we are flying economy.
When we boarded and they realised they were in Singapore Airlines business class, my son’s face completely changed. He looked at me with an expression I will never fully be able to describe. And then he said “thank you Mommy, thank you Mommy”, over and over again.
Singapore Airlines was extraordinary on every level. The flight attendants brought the kids little gifts when we boarded.
At one point during dinner one of the flight attendants quietly noticed my daughter struggling to cut her chicken and came over without being asked and cut it up for her. As a mum, those are the moments that stay with you.
My son built LEGO for hours. We had a full course meal and slept flat. Nobody said are we there yet. 17 hours passed and it felt like nothing. We landed in Singapore, well rested and ready to explore one of the world’s best airports Changi International Airport. I could barely wait for my kids to experience it.
Singapore to Koh Samui: Scoot via Singapore Airlines KrisFlyer
Points used: 42,000 KrisFlyer miles
Taxes paid: $240
Cash price: $1,796
Here is something I discovered during my research that genuinely surprised me and saved us a significant amount of money.
You can book Scoot Airlines flights using Singapore Airlines KrisFlyer miles. Scoot is a budget airline but it is a Singapore Airlines partner, which means award seats are bookable through the KrisFlyer programme.
The way it works is that you do not book on the Singapore Airlines website. You go to the Scoot website directly, but when you log in you use your Singapore Airlines credentials. That gives you access to book Scoot flights with your KrisFlyer miles.
This was one of those things I only found out during the research process for this trip and I am so glad I did because it kept our remaining KrisFlyer miles working hard instead of going to waste.
The arrival into Koh Samui airport was one of the most beautiful airport experiences of the entire trip. It is completely open-air, surrounded by tropical trees and flowers, and instead of a jet bridge a little trolley picks you up right from the plane and takes you through customs.
The kids stepped off onto the tarmac and started doing cartwheels. I knew right then that Koh Samui was going to be something special.
Koh Samui to Chiang Mai: Bangkok Airlines via Qantas
Points used: 32,000 Qantas miles for 2 passengers
Cash paid for 2 passengers: included in the $464 taxes and tickets
Cash price: $880
This booking required a bit of creative problem-solving that I want to walk you through because it is a great example of how to handle situations where award availability is limited.
I found this route on Seats.aero, which is one of the best tools available for searching award flight availability across multiple programmes at once.
Here is the issue I ran into. Qantas, like many airlines, only releases two award seats per flight for certain partner airlines. So I could book two of us on points but the other two passengers needed a different solution.
Rather than abandoning the points redemption entirely, I booked two seats using 32,000 Qantas miles and paid cash for the other two tickets. Splitting the booking this way let me preserve the points value where I could while still getting everyone on the same flight.
Chiang Mai to Bangkok: Vietjet Airlines
Cash paid: $312
This was the one leg of the trip where paying cash made more sense than using points. Short domestic hops on budget carriers within Thailand are often priced low enough in cash that spending points on them does not make mathematical sense.
I am completely at peace with this. Knowing when to pay cash and when to use points is part of the strategy.
Bangkok to the United States: Condor Airlines via Alaska Miles
Points used: 340,000 Alaska Atmos Rewards miles
Taxes paid: $561.32 for all four passengers
Cash price: $14,000
For the return trip I considered several airlines including Singapore Airlines, Qatar, and Emirates. Qatar actually had two saver rate seats available at 70,000 points per person from Doha to the US, but I would also have needed to figure out how to get everyone from Bangkok to Doha and find the additional seats for the other two passengers.
I do not like putting all my eggs in one basket when it comes to award availability, so I kept researching.
That is when I found Condor.
Condor Airlines is a German airline that flies from Bangkok to JFK and so many other routes. I discovered that you can book Condor flights using Alaska Atmos Rewards miles, and when I searched for availability on our travel dates I found four seats available in business class for 85,000 Alaska miles per person. For four of us that meant 340,000 Alaska miles total.
Now I needed to figure out how to get 340,000 Alaska miles.
My husband had opened the Alaska Atmos Summit card which came with a 100,000 mile welcome offer. We had both also opened the Hawaiian Airlines card which gave us 70,000 miles each. Because Alaska and Hawaiian had completed their merger, we were able to move our Hawaiian miles directly to Alaska.
That gave us 240,000 miles right there. On top of that I had previously transferred 150,000 Amex points to Hawaiian Airlines through a backdoor that existed at the time, not something I always recommend unless you have a specific plan, but I knew Alaska miles were valuable and I wanted a reserve.
When this Condor opportunity came up those miles were sitting ready and waiting in my Alaska account. Between all of these sources we had exactly what we needed.
We booked all four seats on Alaska for 340,000 miles and $561.32 in taxes for business class from Bangkok to New York. A flight that would have cost over $14,000 in cash.
The cards that made this flight possible:
Alaska Atmos Summit card
Hawaiian Airlines card
And yes, I told the kids we were flying economy on the way home too. Same poker face. Same questions from my son every few minutes at the airport. And the same reaction when they boarded and realised they were in business class again. “Thank you Mommy. Thank you Mommy.”
I will never get tired of hearing that.
The Hotels
Singapore: Singapore Marriott Tang Hotel for 4 Nights
How we paid: 4 Marriott Bonvoy free night certificates from a welcome offer
Out of pocket: $0.
Breakfast included thanks to status.
Cash value: $1,800
The four free night certificates that covered this entire Singapore hotel stay came from a Marriott Bonvoy credit card welcome offer. The offer was get 5 free nights after spending $4000 within 3 months. Marriott releases these offers occasionally so I recommend being on the look out for it as it can save you thousands of dollars.
This is exactly why I pay such close attention to what welcome bonuses actually include: not just points but certificates, credits, and other benefits that have real dollar value when you deploy them correctly.
Four free night certificates on a single card application covered a family of four for four nights at one of Singapore’s most iconic hotels right in the heart of Orchard Road. Zero dollars out of pocket. Breakfast included every morning because of our Marriott status.
Koh Samui: Hyatt Regency Koh Samui — 5 Nights
How we paid: 75,000 Hyatt points transferred from Chase
Out of pocket: $0.
Breakfast included thanks to status.
Cash value: $5,900
I transferred 75,000 Chase Ultimate Rewards points to World of Hyatt at a 1:1 ratio to cover this stay. Chase is one of the most valuable transferable points programmes available and Hyatt is consistently one of the best hotel transfer partners in the Chase ecosystem, particularly because Hyatt does not charge resort fees on award stays.
When we checked in we were upgraded to a one-bedroom oceanfront private villa. A private infinity pool. Direct ocean views. Five nights of this for 75,000 points that I had transferred from my Chase account.
The upgrade happened because of our Hyatt status, which we build through a combination of credit card spending and organic stays.
This is something I always want people to understand; hotel status is not just for frequent travelers. The right cards can give you status that unlocks upgrades and benefits like this one.
Chiang Mai: Intercontinental Hotel Chiang Mai The Mae Ping by IHG: 3 Nights
How we paid: Chase Sapphire Reserve $250 IHG hotel credit plus 40,000 Chase points via Points Boost
Out of pocket: $0.
Breakfast included in rate.
Cash value: $881
The Chase Sapphire Reserve comes with an annual $250 hotel credit for IHG properties, $500 Edit hotel credit and $300 travel credit. We used the IHG credit alongside Chase Points Boost to cover the entire three-night stay at zero dollars out of pocket.
This is one of those card benefits that most people leave unused every year and it is worth real money when you deploy it intentionally.
Chase Sapphire Reserve
Chase Sapphire Reserve for Business
And Chiang Mai gave us the most unexpected and emotional moment of the entire trip.
My sister surprised us. She flew out without my kids knowing she was coming and was waiting when we arrived in Chiang Mai (of course I knew because I helped her book her entire trip with points 🙂). That surprise is one of the most beautiful memories I have from the whole 16 days.
Bangkok: Park Hyatt Bangkok for 2 Nights
How we paid: Two Amex Platinum Fine Hotels and Resorts credits of $300 each
Out of pocket: $188.
Breakfast included thanks to status.
Cash value: $788
My husband and I each hold an Amex Platinum Business card, which means we each have a separate annual $300 Fine Hotels and Resorts credit. We stacked both credits against our Park Hyatt Bangkok stay and paid only $188 out of pocket for two nights at one of Bangkok’s most celebrated luxury hotels.
This is another example of a benefit that most people holding the Amex Platinum are not fully using. If you hold two Amex Platinum cards in your household you have $600 in annual Fine Hotels and Resorts credits available every single year.
The Itinerary
Singapore: Days 1 to 4
We landed at Changi International Airport around 7pm after 17 hours of flying and instead of going straight to the hotel we spent two hours at the airport because Changi simply does not let you leave without making you fall a little bit in love with it.
The kids discovered the giant slide, watched the waterfall show, and scooted around the terminal until we finally dragged everyone to the taxi line at 9:30pm.
Over the next four days we covered Gardens by the Bay including both the Cloud Forest and Flower Dome, the Museum of Ice Cream which the kids absolutely adored, Sentosa Island with Universal Studios and the Skyline Luge which the kids wanted to ride over and over again, and the Jewel at Changi on our final Singapore morning.
We booked all our attractions on Viator through Rakuten, so every tour and ticket earned us extra rewards on top of what our credit cards were already earning.
If you are not using Rakuten yet, it is one of the easiest ways to earn more on spending you are already doing. You simply click through Rakuten before you shop, and the rewards land in your account. Sign up with my link and you will get $50 after your first purchase.
We took the MRT train everywhere, which is one of the most seamless and easy transit experiences I have had in any city traveling with kids.
And we ate at the hawker markets almost every night because the food was incredible and experiencing an open-air food hall buzzing with locals and tourists eating together is something I want my kids to carry with them.
If you are planning a Singapore trip and can only choose one indoor attraction, choose the Cloud Forest over the Flower Dome. The 35-metre indoor waterfall is one of the most breathtaking things I have seen in any city across 35 countries.
Koh Samui: Days 5 to 10
After four days of constant movement in Singapore, Koh Samui was exactly the reset we needed. Five nights with no agenda, no rush, and nowhere to be.
Watersports and snorkelling, floating breakfast in our villa, massages almost every afternoon, a pedicure day with my daughter that I will hold close for a long time, evenings at the Night Market, and the fire show at Coco Tam on the beach that the kids have not stopped talking about since we got home.
This was the part of the trip where I remembered why we work so hard to make these experiences happen.
Chiang Mai: Days 10 to 13
Tiger Kingdom was something I had to be talked into. My husband thought it would be amazing. I thought it sounded terrifying. I told myself I would go but I would absolutely not be touching any tigers.
And then I ran away the first time one opened its mouth and roared in my direction. Full retreat. My husband laughed until he could barely stand up.
But I went back. With my sister. And I petted the tiger. And then Laolu decided the tiger was his best friend but the tiger had some very different opinions about that and I have never moved so fast in my life.
We visited the Elephant Sanctuary next and it was a completely different kind of experience. Quieter. More humbling.
Watching our kids interact with those animals with such gentleness and curiosity reminded me of one of the core reasons we do all of this. We want our children to grow up knowing that the world is bigger and more beautiful and more diverse than the neighbourhood they grew up in.
We ended Chiang Mai with a full massage day and one final night market before moving on to Bangkok.
Before we slowed down, we also went on ATV rides, which gave our time in Chiang Mai a completely different kind of adventure after the quiet of the sanctuary.
Bangkok: Days 13 to 16
Bangkok was our final stop and it gave us exactly what we needed to close out 16 days on a high. We caught the new Spiderman movie at the SF World Cinema inside Central World on arrival night because after 16 days of sightseeing sometimes you just want to sit in a cinema with your kids and eat popcorn.
We visited the Space and Time Cube Museum, explored the city’s incredible street food scene and night market, and spent our final full day on a river cruise through the heart of Bangkok as the sun went down.
And then we flew home in business class without the kids expecting it. Again.
The Numbers
| Flight or Hotel | Points Used | Out of Pocket | Cash Value |
| Southwest Baltimore to SFO (kids flew free via Companion Pass) | 30,000 Southwest points + Companion Pass | $22.40 | Included |
| Singapore Airlines SFO to Singapore | 428,000 Amex to KrisFlyer | $22.40 | $26,000 |
| Scoot Singapore to Koh Samui | 42,000 KrisFlyer | $240 | $1,796 |
| Bangkok Airlines Koh Samui to Chiang Mai | 32,000 Qantas (2 passengers) + cash for 2 | $464 | $880 |
| Vietjet Chiang Mai to Bangkok | Cash | $312 | $312 |
| Condor Bangkok to USA | 340,000 Alaska | $561.32 | $14,000 |
| Singapore Marriott Tang Hotel 4 nights | 4 Marriott Free Night Certificate | $0 | $1,800 |
| Hyatt Regency Koh Samui 5 nights | 75,000 Hyatt from Chase | $0 | $5,900 |
| Intercontinental Chiang Mai 3 nights | 40,000 Chase + $250 IHG credit | $0 | $881 |
| Park Hyatt Bangkok 2 nights | 2 x $300 Amex FHR credits | $188 | $788 |
| TOTAL | 1,157,000 points | $1,787.72 | $52,357 |
PS: Both my husband and I hold the Southwest Companion Pass, so we booked our own seats with about 15,000 Southwest points each and added our two kids as companions. The kids paid just $5.60 each in taxes, which means four of us flew across the country for 30,000 points and next to nothing in cash.
Note: This does not include activities, food, shopping, or local transportation. All of those were paid with credit cards to continue earning points while we traveled.
The Tools We Used
Seats.aero: for searching award flight availability across multiple programmes at once. This is where I found the Bangkok Airlines route from Koh Samui to Chiang Mai and the Condor flight from Bangkok to JFK.
Singapore Airlines website: for searching KrisFlyer saver rates across multiple US departure airports.
Alaska Airlines website: for searching Condor availability using Alaska miles. Seats aero found the deal and I confirmed availability on Alaska
Rakuten: for booking Viator attractions and earning extra points on every activity booking.
What I Want You to Take From This
Start early and search one way. We booked our long-haul flights nine months in advance, searching each direction independently. Award space for families traveling together is genuinely harder to find than for solo travelers or couples and the earlier you start the better.
Let the flights shape the itinerary. Once we had Singapore Airlines confirmed out of SFO and Alaska miles locked for the return on Condor, everything else fell into place around those anchor bookings.
Be willing to position. Flying Southwest from Baltimore to San Francisco to catch a Singapore Airlines deal was absolutely worth it. The right deal is not always out of your home airport.
Build your card portfolio with a plan. The points that funded this trip came from specific card decisions: the Amex Business Platinum and Business Gold for Singapore Airlines, the Alaska Atmos Summit and Hawaiian card for Condor, the Marriott Bonvoy card for Singapore hotel, the Chase Sapphire Reserve for the IHG credit, and two Amex Platinum cards for the Park Hyatt credits.
Each card had a job to do and we opened them intentionally.
Stack your hotel benefits. The free night certificates, the IHG hotel credit, the Amex Fine Hotels and Resorts credits all came from cards we already held. Most people have benefits sitting unused on cards they already carry in their wallet.
And the last thing, the one I come back to every single time someone asks me why I put so much energy into learning this. I think about what this trip would have cost five years ago before I started paying attention to points. $52,357. A number so far out of reach for most families it would never even be considered a real option.
We paid $1,787.72.
Our kids flew business class across the world and said thank you Mommy and meant it in a way that had nothing to do with the seat and everything to do with knowing their mum had figured something out that most people do not know exists.
That is why I do this. And that is why I want you to do it too.
Ready to Plan a Trip Like This for Your Family?
Everything we used to book this trip came from everyday spending: credit card welcome bonuses, grocery runs, rent payments through Bilt, and online shopping through Rakuten. Nothing complicated. Just consistency and intention over time.
If you want to build a strategy around your specific spending and your family’s travel goals, book a one-on-one session with me and we will map it all out together.
Book Your One-on-One Strategy Session Here
Estimated cash values are based on publicly available flight and hotel pricing at the time of booking. This post contains affiliate links. All opinions are our own.
