As we near the winter holiday season, I’ve started planning a New Year jaunt to celebrate my recent nuptials. We already planned to visit the West Coast after Christmas, and since there was an expiring Alaska Airlines Companion Ticket in the mix, I decided to see if I could use the West Coast as a stopover to one of Alaska’s more far-flung destinations. Alaska offers nonstop flights from Portland to several Hawaiian islands, so I checked award availability at one of Hilton’s top-tier, 95,000-point properties: the “Grand Wailea, A Waldorf Astoria Resort.”
Transferring Hilton Honors points is now free and fast (but not instant)
I was surprised to see that for 5 nights right after the New Year, the Grand Wailea had wide open award availability for their standard “Terrace View” room. There was no way I was going to book anything less than a 5-night stay at a 95,000-point property, thanks to Hilton’s fifth-night-free policy on award stays for elite members. But a 5-night stay would still cost 380,000 Hilton Honors points, more than I happened to have in my account. Even after cancelling a couple Hilton reservations and rebooking those stays at Hyatt properties, I was about 100,000 points short.
That’s when I remembered that as part of the April 2, 2018, revamp of the Hilton Honors program, “points pooling” and “points transfers” are now free between all members. Let me start by saying it’s not immediately clear to me exactly why Hilton distinguishes “pooling” from “transfer” transactions: in both cases only the recipient of the transfer, or the creator of the pool, is able to redeem the points, and in both cases the contributor of the points is able to select the number of points they want the recipient to be able to redeem.
The limits on transfers and pooling are somewhat complex, so let me start by sharing the terms and conditions as they’re presented on the Hilton website:
“Hilton Honors Members can transfer Hilton Honors Points to another Hilton Honors Member through Points Pooling or 1-to-1 transfer in increments of 1,000 Points and up to 500,000 Points. Each Hilton Honors Member is limited to sending no more than five hundred thousand (500,000) Points and receiving two million (2,000,000) Points via Points Pooling or Transfers combined per calendar year. Each Hilton Honors Member is limited to making six (6) transfers to other member accounts and six (6) Hilton Points Pooling transactions per calendar year. Invitations to join a Points Pool is not considered transactional. Transactions refer to the transfer of Points to another member account either through 1-to-1 account transfers or through Points Pooling.”
There are three moving pieces here:
The total number of points you can send in either transfer or pooling transactions per calendar year (500,000);
The total number of points you can receive in either transfer or pooling transactions per calendar year (2,000,000);
The total number of outbound transfer and outbound pooling transactions you can make per calendar year (6 transfer and 6 pooling transactions).
That’s my plain English reading of the terms and conditions, but if anyone has run up against these limits in practice or found a way around them, let me and your fellow readers know in the comments.
All that being said, yesterday I asked a travel hacking buddy to transfer over the points I needed to book my 5-night stay at the Grand Wailea. Then I waited. And waited. And waited.
Ok, I only waited about 11 hours, but the point is, don’t expect points transfers to take place immediately, and don’t count on them if you need points for an immediate redemption.
I received a confirmation e-mail (as did the person sending the points) a few minutes after noon the day after the request, so it’s possible they run a batch process every day at noon to execute the previous day’s transfers.
I redeemed 380,000 points for a $8,466 stay
The stay I redeemed 380,000 points for would otherwise cost:
$7,199 room rate;
$200 resort fee;
and $1,067 taxes.
That gives an almost comical 2.2 cent per Hilton Honors point redemption, or 13.2% in value on my grocery store manufactured spend, where I earn 6 Hilton Honors points per dollar on my American Express Ascend card.
You may remember that as part of the April revamp of the program, Hilton no longer excludes Waldorf Astoria resorts from the Gold and Diamond elite breakfast benefit. After reaching out to the property for an explanation of their benefit, the “Room Reservations Agent” explained that:
“You would receive a daily $15.00 per day up to 2 person a in room dining credit. Unfortunately the $15.00 in Only for in Room dining" [sic].
Being a pedant, I looked up the Grand Wailea’s in-room dining menu, and there actually are several items at or below the $15 price point. I hope you like avocado toast as much as I do!
Did I overpay?
To be clear, I booked this particular top-tier property mainly for the blog content, since I couldn’t find any useful information online about how Diamond benefits there work in practice.
But, being me, I also did a quick rundown of alternate properties, in case you want to go to Maui for some reason besides getting a couple good blog posts out of it. Here are the properties that still have award availability as of today:
Wailea Beach Resort - Marriott, Maui. 200,000 Marriott Rewards points for a 5-night stay.
Days Inn by Wyndham Maui Oceanfront. 75,000 Wyndham Rewards points for a 5-night stay.
Of course, money can also be exchanged for goods and services, and some light browsing turned up what seems like a pretty good deal through Agoda.com, for a total of $2936.03 for five nights at the Hyatt Regency Maui Resort and Spa, a rate that even includes breakfast.
Using 200,000 Marriott Rewards points (worth $2,000 in cash if transferred from Ultimate Rewards) and $2,936 as my most likely alternatives, I redeemed 380,000 Hilton Honors points at between 0.5 and 0.77 cents each, a solid but unremarkable redemption.
Obviously that’s not going to stop me from bragging to friends and family about my $8,500 honeymoon.
I’m very curious how this trip will work out, since after reading a slew of reviews online it seems like the Grand Wailea changes their policies every few weeks. My conservative hope is an upgrade from our standard “terrace view” room to at least an ocean view room, since that was one of the delights of our stay at the Hyatt Zilara Rose Hall. The property also has what looks like an all-suites tower, which Hilton Diamonds seem to very occasionally be upgraded to for free (paid upgrades are also available).
We plan to rent a car in order to see some other parts of the island, which means at a bare minimum paying $30 per day for valet parking, since the hotel doesn’t have a self-park option. Given the certainty of those expenses, plus any food and drinks we charge to our room, I’m thinking hard about whether to sign up for an Aspire card before we make the trip. I have the option of upgrading my Ascend card, which would sacrifice my bonused grocery store earning rate, so that’s of marginal interest. But my partner has never had a Hilton credit card and she’d be eligible for the current 150,000-point signup bonus, plus a $250 resort credit during our stay.