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​Where Amex points are worth the most​

by Darren Murph Named an “oracle of remote work” by CNBC, Darren is a recognized speaker, consultant, and advisor. He holds a Guinness World Record in writing, earned while visiting 50+ countries using points.

Hi, Reader. As any travel enthusiast will tell you, there's a special kind of pressure that comes with planning a milestone trip. For my wife's big birthday this year, I wanted to create a truly unforgettable experience.

The destination: Santorini, Greece. The challenge? Finding the perfect stay that balanced luxury, family-friendliness, and a sensible budget.

Here's how my family's travel advisor saved the day by helping us get the right room and extra perks through the Hilton for Luxury program.

When points aren't the answer

My heart was set on Sandblu Santorini, a stunning resort on the island's quieter eastern coast. It had everything we were looking for: incredible views, it was walkable to a beach, and it had a serene, family-friendly vibe.

I eagerly went to book it with points, but I hit a familiar wall. The base-level room wasn't quite big enough for our family, and the premium suites — the ones that would fit us comfortably — demanded an astronomical number of points.

I was sitting on a healthy stash of points, but they weren't the right tool for this specific job. The value just wasn't there. Then, I remembered a lesson I'd learned a while back: Sometimes, the best hack is knowing when to ask for help. I pinged my travel advisor, Lindsay, and what she discovered made all the difference.

The travel advisor's secret weapon: Hilton for Luxury

Sandblu Santorini had recently joined the Hilton portfolio as an LXR Hotels & Resorts property. Our travel advisor, Lindsay, then introduced me to a program I'd overlooked: Hilton for Luxury.

By booking a discounted cash rate through her via the Hilton for Luxury program, we could secure the exact suite we needed.

I have Hilton Diamond status thanks to my Hilton Aspire American Express card, so I knew I'd also get my usual perks. However, this approach is really beneficial for those who don't have Hilton status. When you book through this program, you're treated to niceties typically reserved for top-tier members.

• Daily complimentary breakfast for two
• A $100 property credit to use during the stay
• Late checkout, subject to availability
• A potential one-category room upgrade at check-in

If you're booking for work, Hilton for Business is another program worth a look — it's free to join and earns bonus points on top of your personal Hilton Honors earning.

Why it was worth every dollar

Not only did we get the spacious suite we needed for our family, but we also got a ton of value-added benefits that would make our milestone celebration even more special. The cash rate, when you factored in all the perks, was a much better deal than the exorbitant points price for the premium room. We didn't have to pay until we reached the property, and I earned 14x points by putting the entire purchase on my Hilton Aspire American Express card.

For anyone with an aspirational Hilton property on their bucket list, using a travel advisor to access the Hilton for Luxury program could be the key that unlocks a stay you thought was out of reach.