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Welcome to the next installment of our Reader Success Series where Million Mile Secrets Readers share how they booked a trip with miles & points to get Big Travel with Small Money! This interview has been edited for content and clarity.
Clint is our newest reader success story to show folks it’s possible to travel without spending a lot of money. If you would like to be inspired by more stories like this one, take a second to subscribe to our newsletter!
What’s your name and how long have you been involved in the miles & points hobby?
My name is Clint, and together with my girlfriend Kim, we have been in the miles and points hobby since 2016. We had just come back from our trip to Jamaica, and realized we could probably be getting more value from our credit cards. I was able to eventually convince Kim to join in on this hobby, and we’ve been maximizing our miles and points for great trips ever since!
What was the goal of your trip?
This was part of our around-the-world trip, and one of our goals was to fly Business or First Class. For the segment of our trip between Japan and Singapore, we wanted to fly on Singapore Airlines, as we had heard it’s one of the best airlines to fly for this segment. And we wanted to book a First Class suite from Singapore to New York as we had read there would be more available award seats for this route.
We had planned a week in Japan, and 3 nights in Singapore. And we had to manage all of this with just 12 vacation days from work, so we had to make the most of our time with booking weekend award flights.
How long did you collect miles and points for your trip?
It took us ~1 year to earn enough miles for this trip. On average, we opened ~1 new credit card every 3 months. I also made sure to do the planning for Kim, so all she’d have to do would be apply for the cards!
Which points did you save to take your trip?
For our First Class flight between Japan and Singapore, we earned a lot of Chase Ultimate Rewards points and ended up transferring them to Singapore Airlines, one of Chase’s many travel partners. A big chunk of the points came from the welcome bonuses Kim and I both earned on cards like the Chase Sapphire Preferred® Card and the Chase Sapphire Reserve® (although for new card members, it is no longer possible to have more than 1 Chase Sapphire product at the same time). I also opened up the Ink Business Preferred℠ Credit Card to get us the last of the points we needed.
For the other legs of our trip, we used our Southwest Companion Pass whenever we could. For instance, we used it on a flight from New York to Los Angeles!
Which cards would you recommend to open for a trip like yours?
I would recommend many of the Chase cards that earn flexible Chase Ultimate Rewards points, so cards like the Ink Business Preferred℠ Credit Card, and either the Chase Sapphire Preferred® or Chase Sapphire Reserve®.
And if you’re looking to qualify for the Southwest Companion Pass, you can open one of the Chase Southwest credit cards as the points from the intro bonuses toward earning the pass!
How did you search and find the award flights?
I had originally started looking for flights ~9 months out. The Singapore Airlines website isn’t the most user-friendly and I was having issues with it. So even though I found available award seats for our flights, I wasn’t able to complete the booking online because the website kept telling me to call in. I got lazy and ended up putting this on the back burner due to work and having to plan other more immediate trips.
About 2 months before our trip, I started looking at award flights again and saw it was going to be difficult finding a Business Class flight at a reasonable price. After some trial and error, we finally booked our flights. We ended up on a waitlist for 5 flights and with all the difficulty of navigating the Singapore Airlines site, we realized we get spoiled with how easy it is to make reservations with Southwest!
How did you find your hotel accommodations?
We didn’t use any of our points for hotel bookings and just shopped for cheap prices on various websites. Since we were going during Cherry Blossom season and I had waited until the last minute to finalize our plans for this trip, it was slim pickings for our hotel accommodations. Even Airbnb’s were a hot commodity and were just as expensive as hotel rooms.
What was the most challenging part of planning your trip? How did you solve it?
As I mentioned before, I was having difficulty booking a flight online with Singapore Airlines. I think it was more difficult since we were also adding a stop in Japan to explore for about a week. I mistakenly booked a flight from Los Angeles to Narita to Singapore without a stop in Japan.
I thought calling in to add a stopover would be easy, but because we had booked an award flight, we encountered some challenges. We were told we had to clear a waitlist for the stopover flight.
It was at this moment I started freaking out about the whole trip. I started frantically texting my buddies, and also tried to get advice from Million Mile Secrets.
So how did we solve it? We arrived early for our flight in Los Angeles to avoid any large crowds, and had one of the ticketing agents help us coordinate with the award booking agents over the phone, in order to modify the reservation to the way we had always intended it to be. We did end up spending a bit more out-of-pocket so it wasn’t the most optimal use of cash, but it was all worth it for us.
I will say that although the online booking process for Singapore Airlines can be frustrating, they make up for it in terms of their customer service. And after this ordeal, my advice to everyone would be to book award flights well in advance of your trip.
Give us a few recommendations or tips on what to do at your destination. Parks, restaurants, hidden gems, etc.
Tokyo Disneyland and Tokyo DisneySea are very different from the Disney Parks in the US as they can develop very long lines with a 3 to 4 hour wait by lunch time. When we were in Disneyland in Anaheim, the longest wait we saw was ~1.5 hours. But even with the long lines, it’s definitely worth the visit, especially Tokyo DisneySea which was very unique! Just don’t expect to hit every ride unless you get there at 6 AM to be the first one in the park and avoid the long lines!
Convenience stores in Japan (such as 7-Eleven) are also amazing. I don’t know how much money I spent there, but you can never go wrong if you are in need of a quick bite or even just want a nice iced coffee. If you plan on going to more than one city in Japan, get a JR Pass so you can get around more easily. We really enjoyed going to Nara to see the deer, and the Kobe beef in Kobe city!
Lastly, if you ever visit Singapore, you have to stay at least 1 night in the Marina Bay Sands hotel. It is truly amazing to see the Supertree Grove at night from your balcony, or the city lights glistening from Marina Bay. You could even catch a Formula 1 race from atop the SkyPark observation deck and enjoy the amazing infinity pool.
What did you learn about yourself on the trip?
I learned you don’t need to be afraid of language barriers because you can naturally interact with anyone and everyone. Neither myself or my girlfriend knew any Japanese but were greeted with nothing but smiles most of the time. We also learned we can travel for almost 14 whole days with nothing but carry-on sized luggage.
It took a bit of planning, especially when we weren’t sure about our flights. But I it’s safe to say we will likely continue the trend on any other long adventurous trips.
What would you say to folks looking to plan a similar trip? Or to those who haven’t taken miles & points trip yet!
Cash in those points before they get devalued! If it wasn’t for the welcome bonus we earned on the Ink Business Preferred℠ Credit Card along with a few referrals, we would have had to postpone this trip another year. And make sure to book early and check often for award flights.
Invest in yourself and use the welcome bonuses to your advantage! Everyone thought I was crazy for originally getting into this hobby. But now that we have traveled around the world and been to almost every Southwest Airlines international destination, I am their go-to person for how to get Big Travel with Small Money!
Want to Share Your Story?
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