Several years ago, when my kids were really little, we took a family trip to Hawaii. It seemed like such a fabulous idea at the time: we would play in the surf, relax on the beach, and soak up the tropical sun while sipping a variety of beverages (Mai Tais for me, pineapple juices for them, everybody’s happy).
The reality is that I barely remember this trip, because I was in such a sleep-deprived fog that everything seemed to shimmer and vibrate. My kids have always been terrible sleepers, and during this particular trip they both woke up at 3:30 am every morning. At 3:31 am on one of those dark mornings, I vowed that we weren’t going to leave our time zone again until they could sleep in. There might have been some tears involved…mine.
So you can imagine my glee and delight when I realized that the time had come for us to venture out of the Pacific time zone. This momentous occasion happened to align perfectly with my discovery of Points and Miles, making it possible for us to choose from pretty much any destination in the world. However, when I asked my family where they wanted to go, they unanimously voted for Hawaii.
I got to work. Planning is one of my favorite parts of this hobby. I love figuring out all of my options and watching the puzzle pieces come together. We wanted to stay for a few nights on Kauai so we could spend time with my cousin, who lives there. Then we wanted to bop over to Maui so we could stay at the Grand Wailea for a few nights.
I have a special “thing” for the Grand Wailea. When I was in my twenties, I was on a game show called “Shop Til You Drop.” My partner and I totally kicked butt and won everything, including a trip to Maui. We didn’t stay at the Grand Wailea, but we ate lunch there (I had the best onion rings of my life at the Maui Onion), and we convinced them to let us see a room. I vowed that one day I would be back. (I do a lot of vowing).
When we travel, we like to book two connecting rooms, one for us and one for our kids. That way, if they happen to wake up at 3:30 in the morning, we don’t have to know about it. So I knew that I would need a huge stash of Hilton points for this trip. To make that happen, here is what I did:
- Josh got a Hilton HHonors Surpass card with a 60,000 point sign-up bonus
- Josh got 2 Citi Hilton Visa cards for 50,000 points each for a total of 100,000 points
- I transferred 145,000 American Express Membership Rewards points to Virgin Atlantic when they had a 30% bonus, then I transferred the points from Virgin to Hilton at a 1:2 ratio. This gave me 390,000 Hilton Points
- I got a Citi Hilton Reserve card (actually, I got two using the double-browser trick, but who’s counting). This gave me 2 free weekend nights for each card. Free nights can be used at any Hilton property.
This is a total of 550,000 Hilton points, plus 4 free nights. More than enough for two rooms, five nights.
The problem was in my timing. All of these points and rewards trickled in over the past few months, so I booked rooms in chunks, because I wanted to lock in some good award prices and make sure that we got the dates we needed. My hope was that after I cobbled together the trip piece by piece, I would be able to call Hilton and have them unify it into one seamless reservation. Prompted by today’s email arrival of my first set of free award nights, I planned to fit my final puzzle piece in today, and top everything off with a triumphant call to Hilton, followed by an announcement at dinner tonight. I imagined high-fives and excited shrieks from my kids as we all celebrated our glorious, imminent return to the scene of our past adversity.
Turns out that the Grand Wailea does not allow one-night stays. I couldn’t simply tack a one-night stay onto my existing reservation, because the system wouldn’t allow it. And I couldn’t simply rebook my stay by putting all the points back in my account and starting from scratch, because the current rates were about 30% higher now than when I had originally booked, so I wouldn’t have enough points for the same rooms.
So things didn’t quite go as planned. We’re currently booked into one oceanview room for three nights. Another night we have two oceanview rooms (connecting). We have 200,000 Hilton points waiting to be used, but oceanview rooms now go for 112,000 points per night. So we could book another two rooms, but then we would have to pay through the nose for the additional 24,000 points. We still need to book a fifth night, because we’ve already booked our flights. And we’ve got a couple of free weekend night certificates that we are unable to use on this vacation.
But you know what? I’m not complaining. This is a problem that I am glad to have. I’ll figure it out somehow. And in the meantime, I am just super happy that we are headed to Hawaii. I’m thrilled that my kids are able to sleep through the night. And I’m so grateful for the points and miles that are making this trip possible.
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