Why I bought 250k Hilton Honors during Daily Getaways

Daily Getaways are over, but while the promo was running, I bought 250k Hilton Honors for $1250 – a solid half a cent a point – and deposited them into my fiancee’s account ( I’ll explain ). Hilton has sales throughout the year, but typically, and there are exceptions to this rule, they sell points at half a cent, usually in the form of buy 80k, get 80k. So, while the price can be had throughout the year, during sale periods, the quantity is harder to come by because Hilton caps each account on total points that can be purchased. Getting 250k in one fell swoop was too good to pass up. Why?

The Waldorf Astoria Maldives.

This is the base room at the Waldorf Astoria Maldives. I’ve never been, it’s kind of a points blogger rite of passage, and by my account, the Waldorf Astoria Maldives looks to be the best resort bookable with points. Maybe even with cash. So, I’ve begun to put together my strategy.

The resort is 120k per night. Below is a rendering of the base Villa ( 2500 sqft with a private pool. )

There is a lot of award space if you’re willing to book on shoulder/off peak, or far out in the calendar. Here’s next April. After taxes and fees…the base room is $3500 a night. The cheapest I’ve seen…$2300. WOW

If you’re a family, good news, these villas permit 2 adults, 2 children as part of the best base rate.

In addition…every villa needs to pay for a boat transfer, which is not cheap.

So, as I see it, the best way to stay at the Waldorf Astoria Maldives is with an Amex Hilton Aspire + 480k Hilton Honors for a 6 night stay. Lemme break it down.

• Nights 1-4 book at 120k a piece
• 5th night free because of Gold/Diamond Status 5th night free on points perk
• Amex Hilton Aspire yields a free weekend night certificate at an Hilton in the world. Deposited in your account shortly after account approval.

Both my fiancee and I have Hilton Honors Gold status via American Express Platinum, so the 5th night is guaranteed whether we acquired an Aspire or not. It and the free breakfast when paying with points are the two biggest benefits, by my calculation, of Hilton Gold status.

This benefit alone will save 120k points on the 5th night + $100 a day on breakfast ( conservative guess of $80 + taxes and service ). Mega benefit.

While getting a 5th night free is great. I’d like to enhance the experience even more with Diamond status, which based on the neighboring Conrad Maldives includes a happy hour and afternoon Diamond reception.

Enter. Hilton Amex Aspire. Extra 150k points.

The card not only comes with Diamond status, but currently, it also includes a 150k welcome bonus after $4k spend in 3months + $250 resort credit ( which could be used to offset the boat transfer, extra food, etc ). Between my fiancee and I, she’s the better candidate as I already have 5 cards with Amex and she has far fewer. So…we sign her up.

Now her account will have Diamond status, and in a few days, also a free weekend night certificate and the $4k min spend will be hit pretty quickly as we’ve been waiting on a few large purchases we need to make.

While not guaranteed, Amex is pretty great about crediting points into your account quickly after the minimum spend is hit. Since we won’t be taking this trip for a little while, it’s not as big a deal, but I’d expect to see the bonus hit her account within a week of the min spend being hit. Amazing.

So…within 2 weeks I expect her account to have 400k Hilton Honors, Diamond Status, and a free weekend night certificate.

The other 80k points.

Hello…my account. I have mid 100s. So I could book a single night on my own, but the best part is I can transfer/combine them into my fiancee’s account. How? Right below.

Go to “More Ways to Use Points” then “Transfer Your Points” you’ll then be prompted as to how many you want to transfer. How many did I do? 110k. That will shore up my fiancee’s account to 360k – enough for 3 nights.

Note the terms and conditions

• Each member can send up to 500k to another member
• Each member can only receive 2M total points in a calendar year
• You can only transfer 6 times in a year.

Why did I do the transfer now?

There will be a window in time where her account gets changed to diamond and her free weekend night will get deposited, but we will still be 120k short of getting that 4th night. I’d guess we will hit the min spend pretty quickly, but it won’t be immediate. So…

I’ll book two different bookings out of her account. The easiest way to do this is to find a 3 night stay ( Tues, Weds, Thursday) that has bookended weekend nights available, all with points. This way I’m hedging my bet in either direction, prior to our 3night stay, or after our 3 night stay that we can add in the additional two nights and throw the weekend cert on it as well. Below is a window that works perfectly next April as there is a Friday night on either side of the booking window ( Hilton Weekend Nights are defined as Friday, Saturday, or Sunday )

So I’d book

• 3 Nights Tuesday, Weds, Thurs
• Free Night Cert Friday

Then once the points are deposited, I alter the Tuesday-Thurs reservation to Sunday to Thursday with the Weekend nights on Friday.  If for some reason the Sunday and Monday prior to check in become unavailable, but the Sat/Sun after are available, I simply change my Weekend Night to Sunday, and add the two nights Friday/Saturday as part of the 5 night.

All in all – I think buying the 250k for $1250, signing up for the Aspire, and getting a headstart on this epic trip made a lot of sense.

I can’t wait to see what the resort is like, what added bennies are thrown in for Diamonds, and fingers crossed…we get upgraded to an overwater ( maybe we’ll pay to upgrade for a night or two )

In total…6 nights on the low end is somewhere around $13800 ( $2300*6) and $21000 on the high end ( $3500*6)

Yes, we paid $1250 for the 250k points to shore up the account, and we’ll have to pay the boat transfer, and $450 annual fee on the Hilton Aspire. But, the $250 resort credit will get eaten up quick, and the Maldives just aren’t cheap. But, in my humble opinion, staying at a place like this is really only doable via points, and epitomizes why I love points so, so much.

Now time to book the flights ( I’m hoping to book something epic like Etihad Apartments )