For about a year before I got engaged, I started opening credit cards left and right, trying to get my hands on as many points as possible. I knew I’d be getting married at some point in the next few years and I wanted to be ready to book one of those insane points and miles honeymoons I’ve seen on other blogs. When I started credit card churning, I thought it would be a good way to travel for less, but I never pictured myself flying first class or staying in an overwater bungalow in the Maldives. I kept earning more and more points and miles and it was surprisingly easy to turn my original plan into something over-the-top and borderline ridiculous. Now that everything’s booked, I wanted to share exactly how I booked my points and miles honeymoon valued at $67,698.23 for only $2,192.23 out-of-pocket.

Forming a Honeymoon Plan and Earning Points and Miles

As I mentioned above, I started stockpiling points and miles for about a year before we got engaged and about two years before the actual honeymoon would take place. I started playing around with itineraries about one and half years before the honeymoon so I knew exactly what flights I needed to book and when. The basic idea was to go to Japan, Singapore, and Dubai and I had enough miles to get us there and back in economy with a business class leg between Singapore and Dubai.

My full plan came together last summer when we decided to get married at the Ritz-Carlton. Full disclosure, getting married there came with 5 free nights at just about any Ritz-Carlton in the world. Was this one of the reasons I picked it? Maybe…don’t tell my dad. Between the time I started planning and we solidified our plan, I had opened so many credit cards that I started to think bigger. Instead of Dubai, we tacked on the Maldives and instead of economy flights, we flying first class up in the sky.

Earning points is the easy part. All you have to do is strategically open credit cards well in advance of when you want to book your trip. If you are planning a honeymoon, it helps to have both individuals involved. If you are worried about spending enough money to meet the spending requirements on all of these cards, I recommend reselling concert tickets or something similar. I was able to spend over $20,000 in one year on tickets alone. I also earned a decent chunk of my points and miles by taking advantage of shopping portal bonuses.

Flight MapOur  Honeymoon Itinerary

Our itinerary is as follows:

  • Night 1 – JFK airport hotel
  • Night 2 – Japan Airlines First Class
  • Nights 3-11 – Japan
  • Nights 12-13 – Singapore
  • Nights 14-16 – Maldives
  • Night 17 – Singapore
  • Night 18 – Singapore Suites

I started by mapping out the flights. I knew we wanted to stay in Japan the longest so it made sense to fly there first. The rest kind of fell into place based on the places we wanted to visit and the fact that I wanted to fly Singapore Suites!

The Breakdown

In this section, I’ll give a brief breakdown of how I booked each portion of the trip. Valuations are based on the cash value at the time of booking. I did not do any manufactured spending. Credit card annual fees are taken into account when reporting out-of-pocket expenses. The totals at the bottom of each section are cumulative. Full details can be found in the specific posts linked at the bottom of the page.

Rental Car and 1 Night at Crowne Plaza JFK

We will be renting a car for $95.72 to drive to JFK. I earned 35,000 IHG points through e-Rewards and made an online booking for the Crowne Plaza JFK (value: $208.16).

Total cash: $95.72
Total points: 35,000
Total value: $303.88

See here for more details.

JFK to Tokyo on Japan Airlines First Class

japan airlines first class

First class to Japan in JAL is 70,000 miles per person. I started “small” by booking two business class seats at 60,000 miles per person. I earned 90,000 miles by opening two Alaska Airlines personal cards and one Alaska Airlines business card. I earned the rest through spending, flying, and the shopping portal.

First class seats on JAL are often not available for award redemptions right away so I recommend trying to nab business class seats first if you can. Note that Alaska charges a change fee of $125 per ticket. This rule went into place after I made this booking. You may be charged the fee for this itinerary change, but I suspect that it could be waived since you are upgrading to a higher class.

japan airlines first class food

Here’s where it gets tricky. Japan Airlines award seats become available on their website and on other partner sites 330 days out. However, Alaska can’t access them until about 325 days out. New seats are posted at 7am EST. Despite seeing two seats available, the system kept erroring out when I tried to book. I called and they couldn’t book them either. The customer service rep noted the seats may become available later. Sure enough, I saw them back on the site later that day and was able to call and book them.

In the meantime, I stalked the Alaska Airlines site daily waiting for first class seats to be released. I opened another Alaska Airlines business card to cover the additional 20,000 miles needed for the upgrade (10,000 miles per person). About four months after my initial business class booking, the seats opened up and I was able to upgrade. In the end, I paid 140,000 miles and $36.20 in fees for these seats worth $27,417.20.

Alaska Airlines credit cards have a $75 annual fee so I paid $300 total in fees. However, both personal cards came with a $100 statement credit so I essentially only paid $100 in fees.

Total cash: $231.92
Total points: 175,000
Total value: $27,721.88

See here and here for more details on booking Japan Airlines award flights.

5 Nights Ritz-Carlton Tokyo

This was a freebie since I’m getting married at a Ritz-Carlton (worth $4,542.20). The hotel handled the booking for us. If we didn’t have this available to us, I would have tried earning Hyatt and Chase points to stay at the Park Hyatt Tokyo.

Total cash: $231.92
Total points: 175,000
Total value: $32,263.28

See here for more details on Japan hotel bookings.

3 Nights Ritz-Carlton Kyoto

I earned 70,000 Starpoints by having both me and my fiancé open the SPG business card from Amex. The annual fee on these cards is waived the first year. To make this booking, I transferred the 70,000 Starpoints to Marriott which equals 210,000 Marriott points. This hotel stay is valued at $4,295.96.

Total cash: $231.92
Total points: 385,000
Total value: $36,559.24

See here for more details on Japan hotel bookings.

1 Night InterContinental Osaka

intercontinental osaka

I used the Free Night Certificate from the IHG credit card from Chase ($49 annual fee). The certificate posts each year on your cardmember anniversary and can be redeemed online. Please note that this property is worth 60,000 points and you can now only use these certificates at properties worth 40,000 points or less. The hotel was valued at $351.95.

Total cash: $280.92
Total points: 385,000
Total value: $36,911.19

See here for more details on Japan hotel bookings.

Tokyo to Singapore on Japan Airlines Business Class

Since we booked our flights to Japan with Alaska Airlines miles, we were able to take advantage of their free stopover perk to fly from Tokyo to Singapore.

Japan AIrlines business class

Here are the basics of Alaska Airlines free stopover as it applied to our flights:

  • You get one stopover per one way ticket
  • Stopovers are generally in the hub city since the stopover has to be in a logical route to the final destination (Tokyo served as our stopover city)
  • You can’t combine multiple Alaska Airline partners when booking a stopover (our flight to and from Tokyo had to be on Japan Airlines)
  • The stopover can be in a third region that is different from your origin and your final destination (our origin [JFK] is in the U.S., our stopover [Tokyo] is in Japan, and our final destination [Singapore] is in Southeast Asia.)

I couldn’t book the stopover at the same time I booked our business class JAL seats because these flights weren’t yet on the calendar. Instead, I called and added them once they became available. Given the change to Alaska Airlines change fee rules, you may be subjected to a $125 fee per ticket if you do it this way.

Our flights were an extra 5,000 miles per person since we were traveling to a different region than our stopover (Japan to Southeast Asia). The additional fees were $23 per person. These flights were worth $6,904.16.

Total cash: $326.92
Total points: 395,000
Total value: $43,815.35

See here for more details on booking a free stopover with Alaska Airlines miles.

intercontinental singapore2 Nights InterContinental Singapore

For our first two nights in Singapore, we’ll be staying at the InterContinental. I used 100,000 IHG points earned through the sign-up bonus for the Chase IHG credit card. The value of this stay is $554.60.

Total cash: $326.92
Total points: 495,000
Total value: $44,369.95

See here for more details on Singapore hotels.

Singapore to the Maldives on Silk Air Economy Class (round trip)

For our flights to and from the Maldives, I transferred 74,000 points from SPG, Amex, and Chase to Singapore Airlines to book two round trip economy tickets worth $985.36. The fees cost $158.83. Economy tickets on Singapore Airlines aren’t in high demand, but I recommend booking early because there are limited flights to and from the Maldives.

Total cash: $485.75
Total points: 569,000
Total value: $45,355.31

See here for more details on booking Singapore Airlines flights.

3 Nights Conrad Maldives

Conrad Maldives Water Villa

This was actually the first thing I booked. I initially forked over 285,000 Hilton points for three nights in an overwater villa worth $3,276. Later in the year, my free night from my Hilton Surpass sign-up bonus posted so I was able to get back 95,000 points in exchange for using the certificate. This change was easy to make over the phone. I earned the points and the free night certificate through the Amex Hilton Surpass ($75 annual fee) and the no fee Hilton Amex. Note that the Hilton Surpass is now Hilton Ascend which carries a $95 annual fee.

Staying at the Conrad Maldives also requires a seaplane transfer to the hotel which costs $1,120 ($560 per person).

Total cash: $1,680.75
Total points: 759,000
Total value: $49,751.31

See here for more details on booking a stay at the Conrad Maldives.

1 Night Conrad Centennial Singapore

We’re spending our last night of the honeymoon at the Conrad Centennial Singapore so I used 79,000 points to book a Centennial Suite at the Conrad Singapore, worth about $362.66. 

Total cash: $1,680.75
Total points: 838,000
Total value: $50,113.97

See here for more details on Singapore hotels.

Singapore to Frankfurt to JFK on Singapore Airlines First Class Suites

Singapore Suites

This was the most costly redemption since we had no choice but to fly back on this specific date. Of course, there were no saver seats on a Saturday on the A380’s most popular route.

To book Singapore Suites from Singapore to JFK, I needed 450,000 miles. I transferred 255,000 Amex points and 195,000 Chase points. I earned the Amex points over the past year with 100,000 from Amex Platinum, 50,000 from Amex PRG, 25,000 from the Green card, 20,000 from Blue for Business Plus, 30,000 by keeping my Platinum open, and the rest from Amex offers and spending.

135,000 Chase points came from my fiancé opening the Chase Ink Preferred and Chase Sapphire Preferred while the rest were from spending and referring my sister to both of those cards.

I paid $450 and $550 for my two years of Amex Platinum card membership, but the fee was effectively $200 because I got $400 back in airline credit and $200 in Uber credit. I also double dipped on the Amex PRG (no annual fee first year) airline credit for another $200 back. The Chase Ink Preferred has a $95 annual fee. After accounting for all of the credits, let’s call it $295 in annual fees.

You can use miles to book Singapore Airlines tickets 356 days out. While the calendar might not allow you to select this date, search the itinerary with the date closest to your actual departure date and click the “Next Day” button. New flights are loaded at 7:00pm EST, so you can hit “Next Day” a second time to access the correct date. I wanted middle seats (hello double bed!) so I made sure to book the moment they were released.

The flight cost $201.73 in fees and was worth $17,353.86.

Total cash: $2,177.48
Total points: 1,288,000
Total value: $67,467.83

See here for more details on booking Singapore Suites.

JFK to Boston on JetBlue

Last but not least, we booked a flight from JFK back to Boston on JetBlue. I used 15,000 JetBlue points to book these flights. I paid $11.20 in taxes and an additional $2.55 in excise tax fees since I transferred 4,250 points from American Express Membership Rewards. This flight was worth $230.40 at the time of booking.

Total cash: $2,191.23
Total points: 1,303,000
Total value: $67,698.23

See here for more details.

DescriptionPoints/Miles UsedCostValue
Rental car to drive Boston to JFKN/A$95.72$95.72
1 Night Crowne Plaza JFK35,000 IHG points$0$208.16
JFK to Tokyo on Japan Airlines First Class140,000 Alaska Airlines miles$136.20$27,417.20
5 Nights Ritz-Carlton TokyoN/A$0$4,542.20
3 Nights Ritz-Carlton Kyoto210,000 Marriott Rewards points$0$4,295.96
1 Night InterContinental OsakaFree Night Certificate$49$351.95
Tokyo to Singapore on Japan Airlines Business Class10,000 Alaska Airlines miles$47$6,904.16
2 Nights InterContinental Singapore100,000 IHG points$0$554.60
Singapore to Maldives on Silk Air Economy Class (roundtrip)74,000$158.83$985.36
3 Nights Conrad Maldives190,000 Hilton Honors points and 1 Free Weekend Night Certificate$1,195$4,396.00
1 Night Conrad Centennial Singapore79,000$0$362.66
Singapore to Frankfurt to JFK on Singapore Airlines First Class Suites450,000$496.73$17,353.86
JFK to Boston on JetBlue15,000 JetBlue points$13.75$230.40

Final Thoughts

If you made it to this point, congratulations, that was a lot of information! Booking a points and miles honeymoon doesn’t have to be complicated. Take it step by step and plan early to have a better shot at booking the flights you want. Even if something isn’t available, there will always be another route you can take or hotel you can stay at…it just may take some more thinking. Sometimes your contingency plan might be even better than your initial itinerary!

Pin It!

A $68,000 Honeymoon for $2,000 Using Points and Miles

Check out the detailed posts from our honeymoon!

Booking the Trip:
My Wedding’s in Less than a Year…Time for Honeymoon Planning!
Honeymoon Update 1: Booking Conrad Maldives
Honeymoon Update 2: Booking Singapore Suites
Honeymoon Update 3: Japan Airlines Business Class to Tokyo
Honeymoon Update 4: Tokyo to Singapore on Japan Airlines Business Class
Honeymoon Update 5: Japan Hotels
Honeymoon Update 6: Round Trip Singapore to Male
Honeymoon Update 7: Itinerary Change – Japan Airlines First Class to Tokyo
Honeymoon Update 8: Positioning Flights
Honeymoon Update 9: Singapore Hotels

Trip Reports:
What to Do in 5 Days in Tokyo
Real Life Mario Kart: A Review of MariCar Tokyo
Exploring TeamLab Borderless in Tokyo
A Sushi Lunch in Ginza
Memory Lane Tokyo: Shinjuku’s Best Yakitori
A Day Trip to Nikko, Japan
A 2 Day Kyoto Itinerary
Hiroshima and Miyajima Day Trip from Kyoto
How to Spend One Day in Osaka
A Complete 10-Day Japan Itinerary for First Timers
A 2 Day Singapore Itinerary
Michelin Star Hawker Stalls in Singapore
Dinner at Odette, a Three Michelin Star Restaurant in Singapore
Dinner at Ithaa Undersea Restaurant at the Conrad Maldives

Hotel Review: Crowne Plaza JFK Airport New York City
Hotel Review: Ritz-Carlton Tokyo
Hotel Review: Ritz-Carlton Kyoto
Hotel Review: InterContinental Osaka
Hotel Review: InterContinental Singapore
Hotel Review: Conrad SingaporeHotel Review: Conrad Maldives Superior Water Villa
Review: Lufthansa Senator Lounge at JFK
Japan Airlines 777 First Class New York to Tokyo in 11 Photos
Singapore Airlines A380 First Class Suites in 10 Photos

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