Also see: 

• Booking Hawaii: Part 1 – Flights for 4 to Honolulu
• Booking Hawaii: Part 2 – Using Citi ThankYou Points for Award Flights on Delta and United
• TripBAM Monitors Your Paid Hotel Rates & Alerts You If the Price Drops

I’ll go ahead and tell you the moral of this story: tend to your reservations.

After booking 4 flights to Honolulu, then adding my little brother into the mix, the final piece of the puzzle was to book the hotel rooms.

Step 1: The paid stay

• Link: Hilton Hawaiian Village

When I visited Hawaii in 2013, my main takeaway was how much I’d like to go back to the Hilton Hawaiian Village and sit on my butt for a solid week. Poetic, right?

Yes, Maui was fun, and I loved the topography of the volcanic Big Island, but I’ll be damned if I didn’t love being in that resort. As schmaltzy, white-bread, and basic as it sounds.

My mom hasn’t traveled much. She’s barely flown. I asked if she wanted to island hop a bit, but she said she’d rather get to one spot in Hawaii and take it all in. Of course I knew just the spot…

Her husband (my stepdad) has limited vacation days, so she said they could stay 4 nights.

4 nights? Ding ding ding – Citi Prestige.

I decided to put my name on the room, add my Mom as a guest, and book it with Citi Concierge.

That’s about ~$228 per night. Not bad, considering I’ll also earn a boatload of Hilton points, hopefully score an upgrade for them, and get a $20 dining credit each day I’m there (for being Diamond).

I immediately plugged the confirmation number into TripBam and settled into the knowledge that Hilton would probably have a sale at some point between booking and arrival.

(Here’s my write-up on TripBam.)

Sure enough, the rack rate fell to ~$200 per night.

So I called Hilton and had them apply my new room rate to the same confirmation number. This is key.

Because all Citi sees is the confirmation number. And they have no idea what portion of the final charge is for the room and what’s for food and drinks. And I’m sure I’ll be adding plenty of Mai Thais to the rooms. 😉

My total charge fell to ~$1,046, but I’ll still get the original ~$269 credit. That brings my room rate down to ~$194 per night – a savings of ~$133 for making a quick 5-minute call to Hilton.

I used this same strategy at the Hilton Tokyo and can confirm I still got the original credit.

This is the importance of tending to your reservations – watch them and stay on top of it! $100 here, $100 there… it all adds up.

In the end, I’m paying ~$777 to bring my Mom and stepdad to Hawaii with me (flights were free). Happy to do it.

Step 2: The award stay

I’m staying 5 nights, so I’ll take advantage of Hilton’s 5th night free on award stays.

The Hilton Hawaiian Village is 50,000 Hilton points per night. But with the 5th night free, all 5 nights cost 200,000 Hilton points AKA 40,000 Hilton points per night. That’s pretty legit.

Booking this was as easy as plugging in the dates and pressing “Book.”

There were technically no award nights available, but I love the soft perk of Hilton giving Diamond guests enhanced award availability.

Between the Citi Hilton Visa (you can still get 75,000 Hilton points and no annual fee) and Hilton stays, it was easy for me to rack up the points. In fact, I already have 100K more, just from staying at Hiltons here and there.

Why I like Hilton

Hilton points get a bad rap, but consider this.

I can stay 1 or 2 nights at a mid-range Hilton and have nearly enough points for an award stay at a Hilton Category 1 (with 1 night) or Category 2 (with 2 nights).

Now look at this 3-night Hyatt stay:

An OK start toward one night at a Hyatt Category 1, I suppose.

But SPG takes the cake:

A night at the Aloft Winchester got me a staggering 270 Starpoints. This is why I don’t care about Starpoints. Man, they give you NOTHING for staying at their hotels!

I also did a proper analysis of Hilton Vs Hyatt status and found Hilton Diamond status to actually be more rewarding than Hyatt Diamond status. And I’ve scored some very nice upgrades this year with Hilton.

So I’m hoping lightning will strike twice and get me and my family an upgrade in Hawaii!

Bottom line

As per usual, this was some seriously geeky stuff.

I hope I’ve outlined my thought process for how and why I booked the hotel stays like I did. And showed how useful it is to stack money-savers like 4th night free with Citi Prestige and lower rates found on TripBam.

While we’re here, can I just say Citi Prestige has saved me over ~$2,500 so far year? And I have 2 more stay credits on the way. I won’t be surprised if I easily surpass $3K in savings with this card.

It’s not a piece of crap until July 23rd, 2017 – maybe. Depends on how much I’ll use the 4th night credit.

At any rate, it will be useful for at least another year, so I’ll pay my $450 and get $250 back after December. I can say with confidence this card is definitely worth $200 until next July.

So the next step is to get there and enjoy Hawaii. Can’t wait to post about it.

This is the first mother-son-family trip I’ve ever taken and I’m so excited. The beauty of combining good deals with points!

Have you booked a stay like this? Any other tips to add to the mix? 

* If you liked this post, consider signing up to receive free blog posts in an RSS reader and you’ll never miss an update!