From Tokyo to Kyoto: Mastering a 11 City Honeymoon in Japan on Points

Introduction

After years of accumulating credit card points, the time had finally arrived to put my plan into action: the dream honeymoon, an extensive two-week, 11-city tour across Japan, entirely funded with points. While I anticipated challenges, the planning process was even more intricate than I had imagined. In this blog post, I’ll provide a detailed overview of how I successfully navigated this complex endeavor, offering insights and strategies to help you craft your own points-fueled honeymoon adventure in Japan.

Inspiration and Planning

If you’re reading this, the allure of traveling to Japan likely needs no introduction. However, the planning process for our points-fueled journey was quite intensive, spanning nearly a year. Regularly monitoring websites for award availability became a routine part of the planning, as we navigated through numerous potential routes and reroutes.

One key piece of advice from the outset: prioritize hotel accommodations. Unlike airlines, where seat availability can open up randomly and sometimes increase as the travel date approaches, hotel bookings with points are more rigid. Once points availability for hotels is gone, it’s rare for it to reappear. This means securing your stay should be top of the agenda in your planning process.

Hotels

We based all our travels strictly on the availability of Hyatt locations during our time in Japan.

Because I was on track to achieve Globalist status early in our trip, which meant complimentary upgrades and breakfast
Hyatt points offer great value, especially at their top-tier hotels. After all, it’s our honeymoon — when else will we have the chance to ball out like this?

Cards Used

Before diving deep into the specifics of hotel bookings and flight redemptions, let’s start with a high-level overview of the credit cards I used for this journey. It’s important to note that this isn’t the only way to plan a points-funded trip; it’s simply a reflection of the cards I had at my disposal and the strategy I employed. This section will outline the cards in my wallet, their role in my travel planning, and the reasons behind choosing each one for this particular trip.

Given that American Express has 18 airline travel partners this was the workhorse
American Express points were transferred to Hawaiian Airlines, Virgin Atlantic, Cathay Pacific and Qantas regretfully (Will go over this one later in the post)

The main bennefit of the Chase Sapphire Preferred for this trip was that Chase is a transfer partner for Hyatt so I was able to use a good amount of Chase points for my Hyatt stays.
It also did a great job of being my catch all card.
If I wasn’t able to book a hotel through Hyatt or a flight through a partner airline I was able to use the Chase portal to book it.
Given that the CSP mutliplies your points by 1.25 when booking through their portal, it helped my points strech a little further
It was also nice being able to rent a car using points instead of cash through the chase portal

The Capital One Venture X card was mainly used to top off Virgin Atlantic points.
I also found it surprisingly helpful in booking small Japan based flights through the capital One travel portal using points
When I first got the card they did not have many partners but over the years transfered partners have increased to those of the American Express program

The Chase Hyatt credit card was instrumental in making this whole trip happen
By Chan and I both having the card we were able to get a decent welcome bonus points offer
Along with the points we strategically both got the card over a year before our trip. This allowed us to get the Hyatt voucher on renewal of the card
The Wold of Hyatt card comes with a $95 annual fee but when the card is renewed you also get a category 1-4 free hotel stay
With the both of us getting this voucher we would be able to use these to cover two night while in Japan

I might be in the minority but I think that the Hawaiian card is somewhat of a dark horse if you’re in one of their mainland routes.
We used the points from this card along with some transferred over from the American Express Platinum card to book our flight from Hawaii to Japan

Total Points Breakdown

When all was said and done, the total tally of points used for our honeymoon came to quite a sum. For hotels and car rentals, we used 733,861 points. For flights, an additional 466,783 points were redeemed. This brings our grand total to 1,200,644 points. In terms of monetary value, this amounted to $38,220. And remember, this figure doesn’t even take into account the added value of room upgrades and complimentary breakfasts we enjoyed.

I’ve added a screenshot of the excel sheet that breaks it all down.

Airline Alliances

I think it’s worth giving a quick overview of airline alliances, a topic so complex it deserves its own in-depth post. Within these alliances, there are variations in booking policies: some airlines allow only round-trip reward bookings, while others permit one-way bookings. In the world of points and credit cards, understanding which airlines offer lower point redemption rates for one-way rewards (as opposed to round-trip options like with ANA) can be a huge advantage. This knowledge enables you to have points in one airline but book flights with another partner within the same alliance. Then, there are unique cases, such as using Hawaiian points for Japan Airline redemption tickets. Such nuances can significantly enhance your travel booking strategy.

Booking Process

In terms of the booking process, it might be helpful to explain everything in the order in which bookings were made using points.

Hotels

Initially, our focus was on selecting hotels that we were particularly interested in, specifically those falling into categories 7 or 8 – the top-tier properties within the Hyatt portfolio. We planned the rest of our itinerary based on the availability of these hotels for reward bookings.

Unfortunately, the Niseko Park Hyatt had no availability for our dates (I’ve come to later learn you need to make longer bookings for award availability to appear), so I resorted to transferring 180K American Express Points to Marriott to secure a stay at the Niseko Ritz instead.

For some other Park Hyatt and Andaz properties that weren’t available through Hyatt reward bookings, I used the Chase portal to book them using points.

The only hotel we paid for in cash was the Ginza Onsen. This was due to the lack of point redemption options. However, in my opinion, the experience and the detour were well worth the expense.

Flights

Now, moving on to the flight bookings, we had a total of 11 flights to account for in our itinerary that unfortunately tuned into 12. Coordinating this was quite time-consuming and required diligent attention to detail and planning. Staying on top of flight schedules, reward seat availability, and aligning them with our hotel stays was a significant part of the planning process.

HNL -> FUK

For a significant part of our planning, I was evaluating various options for the most cost-effective flight from Hawaii to Japan. Considering we were getting married in Hawaii, which is relatively closer to Japan compared to the mainland United States, it made sense to look for flights from there. I researched all the airports with connections between Hawaii and Japan. Eventually, I stumbled upon an incredible deal: two first-class tickets on Hawaiian Airlines for just 65K points one way. To put this in perspective, normal first-class seats for such routes are typically around 110,000 points one way, making this find an absolute steal.

Regularly checking the American Express transfer portal is a wise strategy, as it occasionally offers bonuses that can significantly extend the reach of your miles. By staying vigilant about these opportunities and topping off my account when advantageous, I comfortably amassed enough points to book our flight. Additionally, I transferred some points from Chan’s account to mine. While there’s usually a processing fee for such transfers, holding the Hawaiian Airlines credit card comes with a perk: this fee is waived. This little detail helped us maximize our points without incurring extra costs.

HNL -> KIX

After securing what I thought was the second most challenging leg of our journey, I focused on finalizing the remaining bookings. However, two months before our trip, a curveball came our way. Hawaiian Airlines canceled the route, which led to the cancellation of our ticket. This put me in a scramble to find a solution. I spent nearly two hours on the phone with the airline, navigating through the rebooking process. Unfortunately, they only offered a basic ticket as a replacement for the first-class seat I had originally booked. The entire ordeal was quite a saga, one that I’ve detailed in a separate blog post, where I share how I managed this unexpected situation and was rerouted to Osaka. HERE

ITM -> FUK

Facing the logistical challenge of KIX (Kansai International Airport) and ITM (Osaka International Airport) being about an hour apart, we had to swiftly adjust our plans. Since the rest of our trip was already meticulously scheduled, this change meant sacrificing just one day in Fukuoka to keep our entire itinerary synchronized and staying one night in the Hyatt Regency Osaka. With no time to search for award availability amidst this tight schedule, I opted to book our revised flight through the Chase portal using points

FUK -> OKA

Securing award availability for a round-trip flight from Fukuoka to Okinawa on our specific dates turned out to be a significant challenge. To tackle this, I managed to book a one-way flight through the Capital One portal, finding an option that wasn’t listed on the Chase portal. This led me to Peach Air, a budget airline in Japan, which perfectly fit our needs. Utilizing this approach, we were able to maintain our itinerary seamlessly without any compromises to our travel plans.

OKA -> FUK

I discovered a flight operated by ANA that perfectly matched our schedule for traveling to Fukuoka. To secure this flight, I had to regularly check the ANA website for award seat availability. Once the seats became available, I promptly booked them through Virgin Atlantic, taking advantage of their favorable rate of just 7,500 points per person.

FKU -> KUM

Securing award availability for flights to Yakushima was particularly challenging. After much effort and considering the limited options, I chose a more straightforward albeit expensive route. I ended up booking the flights through the Chase portal, opting for simplicity and convenience despite the higher cost.

KUM -> FUK

When searching for award availability, I frequently used the Qantas and British Airways websites when it came to Oneworld airlines. Through these platforms, I discovered that transferring American Express points at a rate of 10,000 per passenger was the most efficient and effective way to book the seats.

FUK -> CTS

This particular leg of our trip was the most challenging, as it involved the ideal non-stop flight to the northernmost part of Japan. Unfortunately, our outbound flight from Yakushima Island was delayed, causing us to miss our connection. Fortunately, while we did not incur any additional costs to rebook the ticket, it did result in an unplanned layover in Tokyo.

CTS -> HNA

This leg of our journey turned out to be surprisingly straightforward, despite initial expectations. I utilized Hawaiian points for a Japan Airlines flight. The process involved calling Hawaiian Airlines directly and providing all the necessary details, but their team efficiently handled the booking.

SDJ -> ITM

Booking another ANA flight was a straightforward process. I opted to use Virgin points for this booking, as they offered the best value for the journey.

HND -> JFK

To date, this has been the most remarkable flight I’ve booked using points — not only because its cash value would have exceeded $17,000, but also because it offered the best business class experience I’ve ever had. Over time, award availability for these seats has become increasingly scarce, and unfortunately, Virgin Atlantic has since raised their point rates. However, it remains an excellent value for those who can snag a booking.

I spent countless months monitoring the United website, not bound to a specific date but rather a particular week for our return. Interestingly, we flew to Japan without these tickets booked, relying on chance. It was only after landing in Osaka that two seats on the same flight became available. I’ve noticed that reward availability tends to open up either far in advance or very close to departure dates.

Without hesitation, I secured these seats. Later, when I spotted availability for a flight a few days later, I promptly rebooked those and was ok paying the $100 rebooking fee. This experience underscores the dynamic nature of award travel and the importance of being both flexible and vigilant.

JFK -> AUS

To conclude our journey, I used the Chase portal to book our return seats to Austin. Reflecting on the experience, I would have preferred choosing Delta for the return flight. The reason being, the Jet Blue terminal we used lacked a lounge, and we didn’t have access to desirable amenities like the American Centurion Lounge or Priority Lounges.

Lessons Learned

This trip, years in the making, required meticulous planning and a considerable amount of effort. However, the result was a treasure trove of lifetime memories. The strategy of stacking introductory bonuses and exercising the discipline to save them proved to be wise decisions. Involving your ‘player two’ – a partner who shares the same travel goals and enthusiasm for points strategy – can turn the anticipation of such a trip into an exciting and shared adventure.

The biggest lesson learned, though, is that things will inevitably go awry. The key is to go with the flow and have a buffer of extra points in case of unexpected events. It’s always better to be prepared and not need them, than to find yourself in a situation where you need them and don’t have enough. This approach not only reduces stress but also ensures that you can enjoy your journey to the fullest, regardless of the hiccups along the way.

Future Recommendations for Points Travelers

Don’t transfer points over until you know the flight or hotel is available – I got burned by this with Qantas, availability showed and when I went to book it their website would not work
To get into Japan they want to see you already have a flight booked to leave. I had to but one before I could check in and cancelled it within 24 hrs and got a full refund.
To book ANA award tickets you have to call into Virgin Atlantic which might have you on hold for a while but it’s the only way to do it.
While checking United Airlines, Qantas, Japan, ANA and British Airways for award availability was hard its the best way to find availability – But also consider award seach tools like Experflyer, Seats.aero and Point Hound. I did see there was a bit of a delay from when the availability showed up and when you got the alert.
Plan Early and Stay Flexible – Start planning your trip as early as possible, especially if you’re aiming for high-demand destinations or travel during peak seasons. Flexibility with your dates and destinations can also open up more options for point redemptions.
Understand Point Transfer Partners – Know the transfer partners of your credit card points program. Transferring points to partner airlines or hotels can sometimes offer better value than redeeming points directly through your credit card’s travel portal.
Diversify Your Points Portfolio – Don’t rely on a single credit card or points program. Different cards offer unique bonuses and benefits. Having a diverse portfolio allows for more flexibility in booking and maximizing value
Leverage Status and Perks – If you have elite status with airlines or hotels, use it to your advantage for upgrades, free breakfasts, or other perks. These benefits can enhance your travel experience significantly.
Consider Off-Peak Travel – Traveling during off-peak times can often mean better availability and lower point costs for flights and hotels. I took a gamble booking most of the hotels and flights in the hopes that Japan would be back open by the time our trip came.

Conclusion

This trip, meticulously planned and executed using credit card points, was more than just a vacation; it was a testament to the power of strategic planning and the rewards of patience and diligence in points collection.

Our adventure stands as proof that with the right approach, a dream vacation doesn’t have to break the bank. Yes, there were challenges and unexpected turns, but each was an opportunity to adapt and learn. The success of this trip has only fueled my enthusiasm for points travel, and I hope it inspires you to consider the possibilities for your own adventures.

Whether you’re a seasoned points collector or just starting out, remember that the world of points and miles is ever-changing and full of opportunities. So dream big, plan carefully, and never underestimate the value of a point well spent. Here’s to many more travels, discoveries, and memories made along the way!