Around the World for $2k or $20k?

It all started with an alert on an unassuming October 9th, 2024 from Roame.Travel. A flight from Singapore to New York, New York with a layover in Frankfurt, Germany in Business Class around my birthday, on one of the world's best airlines, Singapore Airlines. Did I buy a return flight to a city in the US I’m not even located in, from a city I technically didn’t even have the means to get to in the first place? Yes, yes I did. But that’s one of the fun parts of travel, if you’re flexible, you can start planning your trip from any point in the journey. I was apparently going to start from the end of the trip and work my way backwards to the beginning. 87,500 credit card points and $173.60 in taxes and fees later, was the start of planning my trip to Asia for September 2025. Yes I plan my trips a year in advance sometimes.

Ok, so I have a flight from a far away destination back to my home continent, not even my home city but that’s, again, a later task for another day. Like, actually, a last minute task because New York and DC are so close that I could do it the day of when I land. Anyway, next was deciding on where else I wanted to go because who goes half way around the world and only makes one stop? Not me! Singapore was always on the list so that was obviously checked off once I got the flight because I was obviously going there. I had also always wanted to go to Japan ever since I found out most, if not all, of the Cherry Blossom trees in DC originated in Japan (don’t quote me on that at all). Did I go to Japan during the Cherry Blossom season? No, but beside the point, it was always on the list. So those two places really drove the trip. I set up more alerts on both Roame.Travel and seats.aero and, about a week later, on October 17th, 2024 I found a coveted Business Class flight on All Nippon Airlines (ANA) to Tokyo, Japan… leaving out of San Francisco, California though. Again, not my home airport, actually on the other side of the country. But again, a later task for another day. Also I say “coveted” because at this time of planning everyone and their mom was trying to find award tickets to Japan so it was a real task. Scooped that Business Class flight up for 52,000 credit card points and $207.80 in taxes and fees.

Now I have a flight returning to the United States and a flight leaving the United States. Halloween rolled around and I got an alert for a First Class flight on Delta Airlines from New York, New York, to Washington, DC. Great! I found an actual positioning flight to get me to my home city. I booked that First Class ticket for 7,500 credit card points and $69.43 in taxes and fees. Don’t get too excited about it being “First Class”. Domestic First Class is nothing fancy and it’s an incredibly short flight. Nonetheless, it still sounds good to be First Class! It’s been a month of planning and I’ve secured 3 Business Class tickets and 1 First Class ticket.

It wasn’t until a month later in my trip planning that I decided to add South Korea to the list, since so many people talk about how awesome it is. Sure enough, after I mentally decided on this addition, the very next day on the 1st of November 2024, up pops an alert for a flight in Business Class from Seoul, South Korea to Singapore on Korean Air. That solidified that I'd be spending 5 days in Singapore and I got the ticket for 40,000 credit card points and $18.20 in taxes and fees.

Another task was deciding how long I would stay in Tokyo, Japan and Seoul, South Korea since this was really the last bit of flexibility left in the planning phase. My Christmas present delivered right on Christmas Day was an alert for a Business Class flight on Japan Airlines. It determined I’d spend 5 days in Tokyo and 3 days in Seoul, South Korea and it only cost me 15,000 credit card points and $38.70. Merry Christmas to me! The trip was really shaping up and I was getting excited.

The last flight I actually booked was the flight out of my home city to start off the entire trip. Chaotic, I know. And that wasn’t until the 31st of March 2025. Remember how I said domestic First Class wasn’t anything fancy? Well, I was a tiny bit wrong in my thinking back then and it wasn't until I watched someone else on social media discuss it that I learned American Airlines offered a quality First Class option with a lie-flat seat. Since I needed to get across the entire country, I looked into it and found routes into San Francisco. The only thing was I had to book an additional positioning flight to New York, New York to catch this flight since it’s so limited. So I booked an economy class flight on American Airlines from Washington, DC to New York, New York for 6,000 credit card points and $5.60 so I could catch my First Class cross country American Airlines flight from New York, New York to San Francisco, California for 39,500 credit card points and $5.60.

In the table below is the breakdown of my flights, dates, countries of origin or if it was a position flight, and their associated costs in points and cash.

Somewhere in between booking all those Business Class and First Class flights, I was also booking my hotel stays. I’ve stayed in Marriott’s, Hilton’s (even worked there for a little bit), IHG’s and other chains but I always personally felt the amount of points to book was always just so high and I wouldn’t accumulate them as quickly as I would have liked. Then I stayed at a World of Hyatt property for a conference and started looking more into them. The points accumulated fast and you could book a decent stay for as low as 6,000 points a night. I’ve stayed at 5 different brands under the World of Hyatt portfolio and I think I’m going to be a Hyatt girlie. So I decided to open a World of Hyatt branded credit card. 

My benefits for opening the credit card were 5 free nights after I met the spending threshold. I used these 5 free night certificates to book the Hyatt Regency Tokyo since this property met the free night criteria. Zero dollars out of pocket for this hotel! In order to meet the spend requirement I booked my Singapore hotel with cash. I was in love with the Andaz Singapore based on pictures and reviews and I knew I wasn’t going to spend enough to earn points to cover this location but I would for the Seoul hotel location. This was the most expensive booking of the entire trip coming in at $3,371.54 for 5 nights at the Andaz Singapore, but, since I was traveling with a friend, we split the cost of this room so I only counted $1,396.55 out of my pocket. Then, with the points freshly accumulated from meeting my spend minimum I booked my 2 night stay at the Park Hyatt Seoul for a total of 50,000 credit card points and zero dollars out of pocket. All 5-star properties!

I also had some points with Marriott left over that I wanted to get rid of so, I didn’t get the best redemption value, but I just needed to use them. I booked a 2 hotels that were relatively close to the airports since I just had some quick overnight layovers. Those cost me 44,000 credit card points and $62.50 for the Fairfield Inn New York JFK Airport and 15,600 credit card points for the Moxy Frankfurt Airport

In the table below is the breakdown of my hotels, dates, countries of origin or if it was a position hotel, and their associated costs in points and cash.

Are we keeping track of the funds spent so far? $1,977.98 total out of pocket for travel and lodging, roughly $116.35 per day for a 17 day trip. In the messy excel table below I did a comparison for myself to truly outline what I just planned. The ‘Points Used’ column is how many credit card points I used from my personal accounts when I received the alerts. Compare that to the column titled ‘All Points’, that’s how many points the item cost at full retail price, which is the full retail price I found at the time I booked the flights with credit card points. Through booking with a combination of transfer bonuses and booking partners, you can see, for some things, I saved points! For most things I only paid taxes and fees, which is why the costs were so low, especially if you compare to the ‘All Cash’ column which is the full retail price I found at the time I booked the flights with credit card points. Green versus red was me weighing which booking option had the better redemption value, points or cash. Sometimes I didn’t always pick the better option, but it depended more on what my available cash was looking like at the time of booking.

Some people coupon, I stalk travel opportunities. You might have $20,527.67 but I surely did not. I did, however, have $1,977.98 and that’s exactly what I spent for 5 Business Class flights, 2 First Class flights, and three 5-star hotels (plus the 2 lesser star and 1 economy) for my birthday around the world. We can dive into the details of each airline and flight, the activities in each city, and the hotels next time we chat!