One of the most meaningful trips I have ever helped with did not start as a Hawaii trip at all.
Kara is a virtual coworker of mine, and her son Sam was diagnosed at 18 with DIPG, a rare and aggressive brain tumor. As Sam was going through treatment, their family learned about a customized vaccine option in Germany. Kara wanted to be able to take Sam, his twin sister Leah, and her husband to Germany for the first vaccine appointment. They knew they would need to make that trip several times, so cost and flexibility mattered a lot.
I got on a call with Kara and her husband and walked them through opening a couple of cards that could help them build the points they would need. They followed the plan exactly, and between the points from their new cards and their UBS points, they ended up with more than enough to cover roundtrip flights to Germany.
Sadly, Sam’s condition worsened, and they were never able to make it to Germany for the treatments before he passed away.
When I reached out to send my condolences, I told Kara that whenever she was ready, I would still love to help them use those points for a meaningful trip in Sam’s honor. A little while later, she reached back out and asked about Hawaii.
That is how this trip came together.
Turning Points Into Something Meaningful
Instead of letting those points sit unused, we used them to help Kara and her family take a special trip to Maui and Kauai. It was a chance to step away, breathe a little, be together, and make memories while carrying Sam with them in a different way.
For flights, they were able to book a single multi-city itinerary that took them from Pittsburgh to San Francisco for a bat mitzvah, then on to Maui, then to Kauai, and finally back home to Pittsburgh with a layover in Denver. The cash price of that itinerary was about $890 per person, but because of how their UBS points worked, each ticket only cost 50,000 points. They did have to book through UBS and pay a $25 fee per ticket, but the points covered the flights once the charge posted. For 3 travelers, that meant they were able to cover a very expensive and complicated itinerary with points instead of cash.
Their Maui Stay
For Maui, they stayed at the Hyatt Regency Maui for 4 nights.
The standard room rate was just 29,000 Hyatt points per night, which came to 116,000 points total for the stay. They booked a room with a king bed and a pullout couch.
One of the best parts of this trip was seeing how generous this community can be. Our Facebook group gifted Kara’s family a Hyatt Guest of Honor award which gives you Globalist status throughout your stay. This made a huge difference. That award saved them 32,000 points compared to what the same room would have cost with Regency Club access, and it also helped them receive an upgrade to an oceanfront room.
That is one of those moments where points are about so much more than math. Yes, the numbers mattered. But the bigger gift was added comfort, better benefits, and a more special experience during a time when their family deeply needed it.
Their Kauai Stay
From Maui, they continued on to Kauai, where they stayed 4 nights at the Grand Hyatt Kauai.
This part of the trip cost quite a bit more in points, especially because they were booking only about 3 weeks in advance.
Their first night was a pool suite for 90,000 points. The other 3 nights were booked as regular rooms for a total of 160,000 points, broken down as 50,000, 55,000, and 55,000 points. That brought the total to 250,000 Hyatt points for 4 nights.
Again, a Guest of Honor award helped. Since the pricier rooms already came with Grand Club access, the biggest value here was that the certificate helped upgrade the 3 regular room nights by one class. From there, they were able to pay cash to upgrade one more level so they could stay in the pool suite for the entire stay.That upgrade cost $200 per night, around $700 total, but Kara said it was worth it. The room gave them more space, more privacy, and some separation from Leah when everyone needed a little breathing room. In a season of grief, that kind of comfort matters.
More Than Just Flights and Hotels
Because they were able to save so much on flights and hotels, they also had room in the budget for some really meaningful experiences together.
They were able to do some amazing excursions, including whale watching and a helicopter tour, which made the trip even more special. Those kinds of experiences are what people remember most, and being able to make space for them after everything their family had been through felt especially meaningful.
Why This Trip Mattered
This was never just about getting a good redemption.
This was about helping a family use points they had earned for one life-changing trip, then repurpose them for a different kind of meaningful trip when life took a devastating turn.
Originally, the points were meant to help Sam get to Germany for treatment. When that became impossible, they became the tool that helped his family rest, reconnect, and honor him together in Hawaii.
That is why we care so much about teaching people how to earn and use points strategically. Points can absolutely help you save money on vacations, but sometimes they do something much bigger. Sometimes they create options. Sometimes they provide comfort. Sometimes they make room for memory-making when families need it most.
And in this case, they helped turn a plan born out of hope for treatment into a trip full of love, remembrance, and time together.
A Reminder That Points Are Not The Point
I think it is easy in this space to focus only on cents per point, luxury upgrades, and optimization. But stories like this are the real reason I love helping people with travel.
Kara and her husband trusted my advice, opened the cards, earned the points, and built a safety net of travel options for their family. Even though the original plan changed in the most heartbreaking way, those points still served a purpose.
They helped this family take a meaningful trip when they needed it most.
And I will never stop being grateful for the way this community showed up too, gifting Guest of Honor certificates that made the trip even more comfortable and special.
That is what this is really about.
-Lisa
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