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Since I earned two Hilton free weekend nights back in May, I have been “agonizing” where I want to spend those two free nights. After weeks of constant mind changing, at 10pm last Wednesday I finally made up my mind. I am heading to Conrad Koh Samui in Thailand!

Where to use my 2 Hilton weekend night certificates

I earned both Hilton free weekend night certificates through spending this year, one from the Amex Hilton Ascend card after $15,000 spending, the other from my old Citi Hilton Reserve card after $10,000 spending (there will be another certificate after $15,000 spending on this card). Hilton issued the certificates a lot sooner than I expected, in less than a week after spending was met, instead of 6-8 weeks as Amex indicated. As a result, both my certificate will expire by mid May 2019.

Read also: 5 Best Use of Hilton Points

Read also: 5 Hilton Hotels to use the Free Night Certificate

Between my work schedule, and a few trips I have already planned for the remainder of this year, my window to travel narrows down to just our winter break during February 2019.  I came up with a few ideas where to burn my two free weekend nights:

  • Waldorf Astoria Amsterdam, 95,000 points  v.s. nightly cash rate over $700, but only one Sunday night is available to use with the certificate; I actually found AA saver awards to Amsterdam from SFO via  Philadelphia, but winter in Europe is not ideal.
  • Boca Beach Club, a Waldorf Astoria resort, 80,000 points v.s. nightly cash rate over $1,200. Award flights to Florida over President’s Day holiday is impossible to find.
  • Hotel del Coronado in San Diego, 94,000 points v.s. nightly cash rate of about $400.  The advantage is that San Diego is just a short easy flight from the Bay Area.
  • Waldorf Astoria Park City over Easter Weekend, 80,000 points v.s. nightly cash rate over $1,100. The two-queen beds standard room is available which is rare. Nonstop flights between SJC to Salt Lake City starts at 8,000 SkyMiles each way.
  • Hilton Aruba, 80,000 points v.s. nightly cash rate of $700. There are award seats on Copa Airlines via Panama, and booking a roundtrip ticket I can get a free stopover in Panama City.

As you can probably tell, I had a hard time making up my mind. I was really leaning towards Aruba, as the idea of a warm beach getaway in February sounded really good. But I didn’t stop there.

2 First class awards from SFO to Bangkok

While browsing for award seats on United website, I accidentally found two first class seats on ANA from San Francisco to Tokyo Narita, connecting to Thai Airways on the A380 jet to Bangkok. That got me really excited, as I have never seen two first class seats on ANA’s SFO Narita flight before.

I flew ANA from San Jose to Tokyo Narita in business class on their Boeing 787 jet a few years ago. and loved the experience very much. I have flown first class on Cathay, JAL and Singapore Airlines, but have yet to try ANA’s first class product. I have never been on an Airbus 380 jet either. So being able to experience both in one trip would be incredible!

Aeroplan charges 107,500 miles for each first class ticket on this route compared to United wanting 140,000 miles. There is probably a cheaper way to book this itinerary, but I didn’t want to lose the seats, I transfered 215,000 Amex points to Aeroplan and within 10 minutes my two tickets were confirmed, and taxes and fees were about $274.Cash fare for this one-way first class ticket was well over $9,400 per person. It will take nearly 17 hours of flying to get to Bangkok from California, but doing it in first class would be a dream! Flying first class on ANA will give me access to United’s new Polaris lounge in SFO International Terminal. I cannot wait to check it out.

4 nights at Conrad Koh Samui

I have read about the Conrad Koh Samui so many times, along with other top Hilton properties in the Maldives and Bora Bora. Never did I think I would be visiting one of them soon. But surprisingly there are actually standard awards available at Conrad Koh Samui for the dates I need and I can use both the free weekend night certificates and points! I called Hilton and booked 4 nights using 2 free weekend night certificates and 190,000 points. The standard award at Conrad Koh Samui is one bedroom waterfront pool villaI will reach Hilton Diamond status this month and hopefully I will get a free upgrade to their Oceanview Royal Retreat Villa.

2 Singapore business class seats from Koh Samui to SFO

Finding award flights coming home proved to be much more challenging. I searched both United and British Airways websites but did not find the ideal flights on Oneworld nor Star Alliance airlines. Knowing that Singapore Airlines only release premium awards to its Krisflyer members, I turned there. Much to my surprise, Singapore is showing plenty award space at 88,000 Krisflyer miles per person. Singapore is a transfer partner of all four flexible point programs, but I have been accumulating ThankYou points for this. So I initiated transfer of 176,000 ThankYou points, and it took about 30 hours to complete.

Searching segment by segment, I was able to find business class availability from Koh Samui to Singapore, operated by SilkAir, a subsidiary of Singapore Airlines.

Award space is also available from Singapore to San Francisco via Hong Kong. 

But the website refused to put all three segments together if I searched Koh Samui to SFO! I called Singapore Airlines and gave each flight information to the very friendly agent, 15 minutes later my tickets were issued. Two business class tickets all the way from Koh Samui to San Francisco cost me 176,000 miles plus approximately $182, the one-way cash fare cost over $3,900 per person!

7 nights in Thailand before Koh Samui

I have seven more nights in Thailand before my stay at Conrad Koh Samui starts. It will my first time in Thailand and I have to decide where to spend that one week  – Bangkok, Chiangmai, or Phuket. I do have some hotels in mind. No matter what the final plan is, my stay will be covered by points:

If you have any other suggestions, I would love to hear them.

Our 1st dream trip

So far I have spent 215,000 Amex points, 176,000 ThankYou points and 190,000 Hilton points, and there are 7 nights of hotel I still need to cover. This trip will put a big dent in the pile of miles and points I have earned over the past two years. But it is why I collect miles at the first place. “Earn-it, Burn-it” is what you are supposed to do when you have the opportunity, otherwise program devaluation will eat your points away.

READ MORE: How i earned over  1.6 million points in 2016 and  2.1 million points in 2017

READ MORE: Putting a dent in my pile of 4.9 million points

This is truly a dream trip – as my middle daughter puts it: “it is epic!”. I am bringing her along. Our last mother-daughter trip was back in 2015 where we went to China for her first real Chinese Lunar New Year experience. Yes, she will miss three days of school for this trip, but in the end, the memory and experience will be well worth it. As my good friend Rayne puts it, “traveling is also education”! We will be joining her in Koh Samui at the end of our trip. we are so looking forward to it!

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