How to Book a Two-Week Luxury Trip to Japan Worth $52,583 – for ~$400/person

This is an Ultimate Guide to booking a luxury trip to Japan for cheap – nearly free. You’ll get a two-week itinerary, complete with details on how to book round-trip business or first class airfare and luxury hotel rooms. I’ll cover the cities of Tokyo, Hakone, Kyoto, Kobe, and Osaka, with information about how to get around!

This epic trip assumes you’re traveling with a partner, and that you and your partner are sharing credit card points. If it’s just you, then you can still follow the plan below. Just divide the airfare points and taxes by 2 and you’re golden!

Let’s get started on this Guide to a luxury trip to Japan for cheap!

Summary of Your Two-Week Luxury Trip to Japan for Cheap

This is what I actually did on my $53K trip to Japan. It details how I got there with my partner, where we stayed, and how we paid. None of this is theoretical, I literally did these things. My partner and I flew first-class, stayed in these luxury hotels, and paid for it exactly as listed below. As of this writing, you can do every single one of these things too!

Logistics: Planning Your Luxury Trip to Japan for Cheap

This is an epic luxury Japan trip that you’re getting to take for over 98% off. So, you should expect that you’ll have to plan pretty far in advance. If you’re starting from scratch, with very few points/miles of any program, you should expect the planning process to take 9-15 months in total. Add about 6 extra months if you’re doing this solo, instead of with a partner. In the table above, you’ll note that this took 7 credit card signup bonuses. If you’re traveling with a partner, that’s 3.5 cards apiece. You need enough time to:

1. Get the cards;
2. Spend enough over each 3-month period (except for the World of Hyatt Card which has a 6-month requirement) to get each sign-up bonus;
3. Book your flights;
4. Book your hotels.

As a general rule, you’ll need to book your flights at least 6-11 months in advance because award flight tickets book up early.

Hotels are quite a bit easier to book using points. You shouldn’t expect to book a luxury hotel a week in advance using points during Japan’s popular cherry blossom season. However, you can generally find good hotel award availability 1-2 months in advance. I’d definitely book my flights first, then book my hotels as soon as I could afterwards. Flights are the gating factor here because award space is so limited. Once you’ve got your flights, you’ve got some time to collect more points to book your hotels.

What did you have to pay in annual fees for this trip?

This would take you 7 credit card sign-up bonuses if you’re starting from scratch. And, two of those cards are “premium” rewards cards with fees of $450 and $550 apiece. That sounds like a lot. But if you actually use the benefits these cards offer, all seven of your annual fees will total only about $600. Here’s how:

1. Amex Platinum card: Annual fee $550, less $200 Uber (or Uber Eats) benefit, less $200 airline incidental credit: Net $150 annual fee
2. Chase Ink Business Preferred: Annual fee $95
3. Chase Sapphire Preferred: Annual fee $95
4. World of Hyatt: Annual fee $95
5. IHG Premier: Annual fee $89
6. Hilton Aspire Card: Annual fee $450, less $250 credits to restaurants, less $250 airline incidental fee credit: Net $0 annual fee. As I’ve said before, I think this card is a STEAL.
7. Capital One Venture Rewards: Annual fee $95.

Total net annual fees: About $600. Note, you can squeeze even more value out of these cards too. For instance, the IHG Premier card gives you a free night worth up to 40K IHG points at your anniversary, and the Hyatt card gives you a free night worth up to 15K Hyatt points. You can’t use them on this luxury trip to Japan for cheap, but you can use them later! The Hyatt Regency Austin and the InterContinental Berlin are great examples you can book with those annual free night certificates, from Hyatt and IHG respectively.

With your Amex Platinum, you also get free lounge access and $100/year (two $50 credits twice yearly) at Saks. The Capital One Venture Rewards card lets you transfer points to a number of programs, and you can get some great value out of the Wyndham and Accor transfer programs. Bottom line, you’ll be paying about $600 in net annual fees….but you can still gain extra value beyond that.

Day 1: Booking Your Business- or First-Class Flight to Tokyo

I flew first-class and highly recommend it, but you could fly business-class using the same method below for fewer points. You need a lie-flat, premium flight if you’re taking a luxury trip to Japan for cheap, right?!

The experience: ANA first-class to and from Tokyo

Others have covered ANA first class in detail, so I won’t obsess too much here. But I just want to say, flying first-class on ANA is like eating Michelin-starred breakfast, lunch, and dinner in bed while watching movies and drinking expensive champagne to your heart’s content. It really is that awesome. Flights to Japan take 11-15 hours from the U.S., which is way too long to sit in economy class. Start your luxury trip to Japan for cheap by flying first- or business-class with ANA.

How to book ANA first- or business-class

Your steps to booking are:

1. Determine where you’re flying from: JFK, LAX, ORD, IAD, SFO, IAH, or HNL. All of these cities offer ANA nonstop first class flights into Tokyo Narita or Tokyo Haneda. If you don’t live in one of those cities, take a “positioning” flight (read: a short economy flight) to get yourself there.
2. Figure out how many miles it will cost. Amex Membership Rewards, Chase Ultimate Rewards, and Citi ThankYou Points all transfer to Virgin Atlantic at a 1:1 ratio, instantly. It will cost 110K miles from the West Coast or 120K miles from Midwest/East Coast for a round-trip first-class ticket. (90K or 955K for round-trip business-class.) It’s totally illogical that you’re going to fly on ANA, but you’re transferring points to Virgin Atlantic. That’s okay, just go with it.
   • Sometimes, Amex offers transfer “bonuses,” where when you transfer 1,000 Amex Membership Rewards, it converts to 1,300 Virgin Atlantic miles. In that case, your first-class ticket from the Midwest/East Coast could cost a mere 93K miles, like one of mine did. But even without the bonus, 110K-120K miles is a fantastic value for a round-trip first-class flight.
3. Collect those miles. The Amex Platinum will get you 60K Amex MRs; the Chase Sapphire Preferred will get you 60K Chase URs; the Chase Ink Business Preferred will get you 80K Chase URs.
4. Figure out the flight numbers that you will take. Do this when you’re getting close to the number of miles you need. No need to figure out the exact dates, but do learn the flight numbers because you’re going to need to learn how to search for awards. Use Google Flights to find nonstop ANA flight numbers from one of the 7 cities listed above into either Tokyo Narita or Tokyo Haneda. For example, NH 111 flies from Chicago O’Hare into Tokyo Haneda. On the way back, it’s NH 112.
5. Use ExpertFlyer to find a Global First – Saver Award, with ANA as the specified airline. Follow the guide here for details and screenshots. Keep those flight numbers handy.
6. Transfer your points, then IMMEDIATELY book those award flights. Be ready to do these things immediately, because you don’t want to find an award flight, then sit on it while someone else books it out from under you. Before starting the transfer process, you should already understand how it works, so that you’re ready to do it all at once. (This is even more important if you’re transferring from multiple programs.) Once the miles are in your Virgin Atlantic account, immediately call Virgin Atlantic to make the booking. Their phone representatives are awesome and they can do it for you.
7. Get your flights ticketed and set up your seat assignments. Remember, you’re booking with Virgin Atlantic, but flying on Al Nippon Airways. So once you get your tickets via email, you’ll want to call ANA to pick out your seat assignments. You should do this sooner rather than later, to get your choice of the best seats. ANA’s phone representatives are also awesome.

If you need more points

If you know you’re going to end up short a few thousand points, there are some strategies for that:

1. Get another credit card. See above for recommendations. If you’re traveling with a partner, have your partner get one of the credit cards that you already got. And even better…
2. Refer your friends or partner to a credit card you already have. I referred my partner to my CIBP and got 20K points just for doing so!
3. Utilize shopping portals. (Honestly, you should be doing this anyway!) Shopping portals are a great way to get an extra few thousand points on stuff you were going to buy online anyway. For no additional cost, you get extra points just for being logged into a shopping portal account and clicking a link from there before making your purchase. Learn more about them here.

Days 2-3: Head to Hakone

You spent Day 1 of your luxury trip to Japan for cheap on a ~14-hour flight to Tokyo. Tokyo’s about 12 hours ahead of the U.S., so it’s now Day 2. I hope you had a fantastic time! You’re going to land in Tokyo and immediately head to Hakone, a train ride away from the Tokyo airports.

Wait, why fly to Tokyo and stay in Hakone first?

Hakone is a hot-spring town an easy train ride away from the Tokyo airports. You might think to yourself, “I just landed in Tokyo, so why wouldn’t I hang out in Tokyo immediately?” Well, I’ve done exactly that before, and I don’t recommend it because if you’re like me, you’ll be 1) jet-lagged and 2) hungover from drinking during the entire 14-hour flight.

Tokyo is HUGE and BUSY. Trust me, you’ll want to have a ton of energy to run around the city. That’s why I highly recommend going to the sleepy, comfortable, beautiful hot-spring town of Hakone for your first two days. Sleep, get yourself un-jetlagged, and eat in a fantastic ryokan – booking details below! – while exploring the Japanese hot-spring experience. You’ll hit up Tokyo at the end of your trip on your way back home, I promise.

Look, if you really want to hit up Tokyo first, you can skip ahead to Day 10 in this itinerary. From a points and miles standpoint, the order of your hotel stays doesn’t matter. And, you might need to arrange your trip according to how many points you have and which hotels have award nights available on which days. But trust me, if it’s possible for you to stay in Hakone your first couple days, it’s worth it.

This is a very efficient itinerary to 1) See a lot of Japan, while 2) Minimizing time in-transit between different cities. You’re on an epic luxury trip to Japan for cheap, so make the most of it!

How to get from Haneda Airport to Hakone

This whole journey will take you about two hours or a little more. That’s only about an hour longer than it would take for you to get from Haneda Airport into the city of Tokyo. Start by taking the Keikyu Line directly from Haneda Airport to Yokohama Station. From there, take the JR Tokaido Line to Odawara Station. Then from Odawara Station, take the Hakone Tozan Line to Hakone Yumoto Station. I recommend www.rome2rio.com for mapping out your trains.

The Aura Tachibana ryokan is a short, cheap taxi ride from Hakone Yumoto. It’s probably walkable in about 20 minutes, but there are a LOT of hills and I don’t recommend it while carrying luggage. It’s worth the ~$15.

How to get from Narita Airport to Hakone

Tokyo’s Narita Airport is further away from the city center than Haneda Airport, so it will take about a half-hour longer. Otherwise, the journey is similar compared to coming from Haneda. In total, this will take you an extra 90 minutes compared to going from Narita into the city of Tokyo.

This trip takes between 2.5-3 hours. Start by taking the Shinkansen Kodama or Shinkansen Hikari (high-speed trains) from Narita Airport to Odawara Station. After that, the journey is exactly the same as from Haneda Airport!

Booking the Hotel in Hakone: The Aura Tachibana Ryokan

There are a couple of chain hotels, for which you could use Hyatt or Hilton points, to book in Hakone. However, I highly recommend staying at a boutique ryokan (a Japanese inn) because of the unique experience. I’ve stayed at a couple ryokans in Hakone and absolutely love the Aura Tachibana. It was an essential part of my luxury trip to Japan for cheap. You can get a room with your own private hot spring on the balcony, like this!

As far as rooms go, you must get the “room with tatami area” because it comes with its own private outdoor hot spring bath! The pictures don’t do this justice. Our private balcony looked out to the mountains. Indoors, our room and bathroom was extremely spacious. Note, this hotel has its own hot spring facilities that are nice and worth a visit, but if you want the full hot spring theme park experience, I’d visit the public facilities of Hakone.

The lobby and surrounding area of this ryokan is beautiful and modern. But the standout is the food. For breakfast and dinner, you get traditional multi-course Japanese dishes; fish is a big highlight. All of the food was beautifully plated and tasted delicious and perfectly fresh. We stayed for two nights, and all four meals were different from one another. At some ryokans, they bring the food into your room, but here you’re seated in the restaurant area. It’s very peaceful and quiet.

The Aura Tachibana is independent, so you can’t use hotel elite points programs to book it. However, you can book this hotel on Hotels.com, and I did. I used a Hotels.com free night credit worth $220 that I applied to cover a partial night here. I also used Hotels.com because at the time, the Capital One Venture Rewards card earned 10X points on Hotels.com bookings. This is no longer the case. I used my 50K point signup bonus for the Capital One Venture Rewards card to wipe out $500 of my $989 bill. The final cost to me was $269: A $989 sticker price, less $500 from my Capital One sign-up bonus, less a $220 Hotels.com credit.

$269 was by far the most I paid in cash for any of the hotels on this trip. It was so worth it, though; we had our own private hot spring, and we shared two incredible, multi-course meals together.

Days 4-9: Head to Osaka

Osaka is a fantastic city in its own right. It’s also a great place from which to explore all of the Honshu region. From Osaka, you can take day trips to see the sacred deer in Nara, the temples in Kyoto, and to eat all the beef in Kobe.

All of these day trips are super easy from Osaka and take between 45-60 minutes via train, door to door. Don’t be afraid of taking public trans literally everywhere in Japan. It’s incredibly clean, safe, reliable, and easy to understand. I had heard these things about Japan before I ever visited, so I had high expectations already. But every time I go back there, my mind is blown all over again by how great the public trans system is.

How to get from Hakone to Osaka

After eating your last breakfast at the fantastic Aura Tachibana, start at the Hakone-Yumoto Station and head to Odawara Station. Then, take the shinkansen bullet train from Odawara to Shin-Osaka. The whole trip will take about 2.5 hours, so bring some snacks and drinks for the train.

Days 4-5: The Conrad Osaka

The Conrad Osaka is, hands-down, my favorite hotel ever. EVER. First of all, Japanese hospitality is amazing in general. If you check out my full review of the Conrad Osaka, you’ll see how they take it one step further. And if you’re a Diamond from Hilton – which I am due to the Hilton Aspire Card – then you’ll be blown away by the benefits.

While you’re at the Conrad Osaka as a Hilton Diamond, you get full hot breakfast and an evening cocktail hour at the Executive Lounge. These were incredibly valuable, easily worth $50/person/day.

Even better, the Conrad Osaka is a great location from which to explore Kyoto, Kobe, and Nara.

Booking the Conrad Osaka with points

The Conrad Osaka runs 80K-95K Hilton points per night for a standard night. Since you’ll be a Diamond with the Hilton Aspire card, you don’t need to pay up for a room upgrade. At the very least, you’ll get upgraded to a room with a swanky view. And since you’re probably gonna be traveling before 2023, when travel is expected to return to pre-COVID levels, I bet you’ll get an even better upgrade – like I did with my experience. Check out my room description in my review of the Conrad Osaka.

To book a two-night stay, you’ll need 160K-190K Hilton points. The Hilton Aspire card gives you 150K bonus points, and you should be able to easily get 160-190K from there. This is because, although Hilton points are worth less than Chase or Amex points, they’re really easy to earn. The Hilton Aspire card earns 14X per dollar on Hilton purchases; 7X points per dollar on travel and dining; and 3X points on everything else. And during the COVID-19 crisis, it’s earning 12X points per dollar on groceries too.

What if you’re short some Hilton points, or you want to stay longer at the Conrad Osaka?

I love the Conrad Osaka so much that if you have the points to stay a few more days, I’d highly recommend it. If you’re a Hilton Silver, Gold, or Diamond elite, which you’d get from the credit cards, you can get your 5th night free for a 4-night booking with points. This hotel costs 80K-95K points per night. So if you can swing 320K+ Hilton points, you’re here for a whole 5 nights!

The first way to get more Hilton points is to get more Hilton credit cards. This itinerary assumes you already got the Hilton Aspire Card. You could also get the following additional cards for even more Hilton points:

• Hilton Honors Business Card: 125K bonus points; annual fee $95
• Hilton Honors Surpass Card: 125K bonus points; annual fee $95
• Hilton Honors Amex Card: 75K bonus points; annual fee $0

You will earn a Weekend Night Reward with Hilton every year for having the Aspire card. You can also get one after spending $15K on either the Honors Surpass or Honors Business cards too. Weekend Night Rewards can be combined in the 5th night free deal.

Another way to get more Hilton points is to transfer them from the Amex Membership Rewards program. Amex MRs usually transfer to Hilton at a rate of 1 Amex MR: 2 Hilton points. Sometimes, they run a bonus of 1 Amex MR: 3 Hilton points. Even then, I don’t normally recommend doing this, because Amex MRs are worth about two cents apiece and Hilton points are worth .5-.6 cents apiece. However, if you’re short ~20K Hilton points for an epic 5-night stay at the Conrad Osaka, go for it.

Days 6-9: The InterContinental Osaka

If I had enough points or free night certificates, I’d stay at the Conrad Osaka forever. But I didn’t, and I also wanted to try the InterContinental Osaka. It’s a great luxury hotel too, don’t get me wrong! But on an average day, it costs less than half what the Conrad Osaka does.

Booking the InterContinental Osaka with points

One awesome thing the InterContinental Osaka has going for it: The IHG Premier card gives you a 140K point welcome bonus (as of this writing), and you get the 4th night free if you book the first 3 nights entirely with points. Each night costs 60K IHG points, so the IHG Premier card’s welcome bonus should almost get you there.

Booking an IHG hotel on points is pretty easy. You can do it online or on the app automatically. If you pick a consecutive 4-night stay entirely on points, IHG will figure out that you get the 4th night free and charge you accordingly for only 3 nights. You can always call to book, but I’ve never needed to.

What if you’re a little short on IHG points?

If you’re a little short on IHG points, you can transfer some from the Chase Ultimate Rewards program at a 1:1 ratio. However, I don’t recommend doing this unless you’re only short ~10-20K points or less. Chase UR points are worth a lot more than IHG points.

One downside to IHG is that their terms and conditions state that you won’t get a free upgrade if you booked a room using points. Sometimes that’s been true for me, such as at the Kimpton Portland; other times, they’ve given me an upgrade anyway, such as at the InterContinental Berlin. Just know that, unlike with Hilton, you can’t expect a free upgrade based on your status.

Days 10-14: Head to Tokyo

After 6 days in Osaka, it’s time to head back to Tokyo for the last 4 days of your epic, luxury trip to Japan for cheap! Remember, you flew into Tokyo but bypassed it to spend your first couple days hot-springing in Hakone. You can spend time in Tokyo on your way back, now that you’re un-jet-lagged. Then head back to the U.S. in first class! How’s that for a luxury trip?

How to get from Osaka to Tokyo

This trip will take 2.5-4 hours on a high-speed train. That’s a significant feat, since driving would cost you 8-9 hours! Start from the Shin-Osaka station in Osaka and either take the Nozomi or the Kodama. The Nozomi is ~2.5 hours and the Kodama is ~4 hours. The Nozomi is faster, but not included in the JR Pass. Either way, pack yourself some snacks and drinks and enjoy going about 160 mph to Tokyo!

Days 10-11: The Conrad Tokyo

The Conrad Tokyo is almost as amazing as the Conrad Osaka; check out my full review of the Conrad Tokyo here. That’s really saying something, since I stay in a LOT of luxury hotels, and the Conrad Osaka is my favorite.hotel.ever.

Just like at the Conrad Osaka, you’ll get Executive Lounge access for free at the Conrad Tokyo. (This is if you’re a Hilton Diamond, which you get if you have the Hilton Aspire card.) And it’s super generous at Conrad Tokyo, too. You’ll also get a welcome gift.

The Conrad Tokyo is extremely well-located and easy to explore Tokyo from. I like the idea of staying here your first couple of days, because you’ll want to take full advantage of the Executive Lounge due to your Hilton Diamond status. And if you’re leaving at the crack of dawn to head home on your flight, you won’t be able to have their awesome breakfast. So stay your first two days at the Conrad Tokyo, and your last two days in Tokyo at the Park Hyatt.

Booking the Conrad Tokyo with points

The process is the exact same as that of the Conrad Osaka, so I’m going to point you over to that section of this itinerary. And, if you want to stay at the Conrad Tokyo longer than two days, you can follow the same advice in that section!

Days 12-13: The Park Hyatt Tokyo

This hotel is in Shinjuku, another neighborhood of Tokyo, that will give you the chance to explore another area in addition to the Conrad Tokyo. The Park Hyatt Tokyo is a fabulous hotel made famous by the movie Lost in Translation, and it’s a great way to get value out of your Hyatt/Chase points. Check out my full review of the Park Hyatt Tokyo here.

Booking the Park Hyatt Tokyo with points

The Park Hyatt Tokyo is part of the World of Hyatt program. It’s a Hyatt Category 7 hotel, which means that it’s normally 30K Hyatt points/night. (Hyatt recently introduced peak and off-peak rates, but dates will center at 30K points per night.)

You can earn Hyatt points by getting the World of Hyatt card, which will give you 25K welcome points after spending $3K in 3 months, and then an additional 25K points after spending $6K in the first 6 months (total). This will get you pretty close to the 60K points required for a two-night standard stay here.

What if you’re short some Hyatt points for the Park Hyatt Tokyo?

If you’re a little short on points, you can transfer them at a 1:1 ratio from Chase Ultimate Rewards. Unlike other transfers I’ve mentioned in this guide, I actually DO recommend transferring points (as many of them as you need) from Chase to the Hyatt program. Chase and Hyatt points are roughly worth the same amount, and the Park Hyatt Tokyo is a great use of Chase/Hyatt points.

Day 14: Head back home in first class after your luxury trip to Japan for cheap!

Whether you’re traveling out of Tokyo Narita or Tokyo Haneda, make sure you check out ANA’s new lounges beforehand. When I flew, their first-class “Suite Lounges” were fine, but nothing special. Recently, like in the middle of the COVID-19 crisis, they updated the Haneda lounges. Rumor has it the Narita lounge updates are next!

Either way, check them out on your way back home.

Then enjoy more champagne and caviar.

I hope you learned how to book an epic, luxury trip to Japan for cheap! If you have questions about any of this, send me an email or post a comment here. I’m happy to help you with your epic trip planning!