The Type B Traveler’s Guide to Finally Using Points

So, I’m that friend. The one booking her hotel on the flight to the destination. The one who buys her full wardrobe after getting there. The one with a non-existent itinerary and a deeply held belief that, “If we just walk outside, something will appear.” Some may call it impulsive, but I like to call it spontaneity with a little bit of chaos. 

I’ll admit it, I’m a Type A person’s worst nightmare… and I had every intention of staying that way. That is, until Hilton invited me on a press trip with a handful of seasoned travel reporters, people who don’t just travel, but optimize it. Over dinner, two of them walked me through how they use points to unlock upgrades, experiences, and thousands of dollars in savings I didn’t even realize I was leaving behind.

And for my fellow Type B travelers who’ve been raw-dogging their way through travel, here’s how one Hilton-hosted weekend in West LA reformed me, without stripping away my go-with-the-flow energy. 

I had just moved from New York to Los Angeles when Hilton reached out to host my Grammy Awards weekend experience.I jumped at the opportunity to attend music’s biggest night and enjoy a little staycation. 

What I didn’t expect was horseback riding in Malibu, multi-course dinners on property, and a suite bigger than my NYC and LA apartments combined, all tied to Hilton Honors, the brand’s loyalty program that gives members access to curated Grammys weekend packages, upgrades, and experiences I genuinely did not know you could redeem with Points.

And before you roll your eyes at the word “points,” I see you. Because if you’re anything like me, “points” sounds like something that requires 47 international flights and a corporate job with unlimited PTO. I am here to tell you: it’s not as unattainable as it sounds. Let’s break it down. 

When you book direct or stay at Hilton properties, you earn points you can actually use, either toward free nights or by combining them with cash. You don’t need some impossible balance, you just use what you have.

But what surprised me most is that it’s not just about rooms. Through Hilton Honors Experiences, Points can unlock actual moments, concert access, VIP sporting events, spa treatments, even Grammy weekend stays at Waldorf Astoria Beverly Hills.

And then there are the small things that quietly upgrade your life: skipping the front desk with a digital key, choosing your room in advance, late checkout when you need it. And truuuust me, a girl like me will always need a late checkout. 

But what if you’re not headed to the Grammys? What if you just want a moment away from the noise?

That’s exactly how I ended up on the back of a horse overlooking the Malibu coastline. Hilton partnered with a local outfitter and handled the logistics, transportation, timing, the whole setup, so all I had to do was show up. It’s an experience I would never, ever plan for myself, but it pulled me completely out of my comfort zone in the best way.

We split our stay between Oceana Santa Monica and Waldorf Astoria Beverly Hills, and they could not have felt more different. The Oceana was rooted in serenity and calm, the type of energy Santa Monica is known for. And if you stay there, head downstairs to the La Monique and grab the Escargot Poppers with garlic herb crème fraîche. Yes, they’re fried snails. And yes, they kind of remind me of mozzarella sticks. Soooo good. 

On the day of the Grammys, we stayed at the Waldorf Astoria Beverly Hills. It felt like a slightly elevated experience and definitely had me feeling like a superstar for the day. The bathroom overlooked the city, the suite was polished and luxurious, and everything about it felt Grammys-coded. When my mom came to visit, we definitely had a pinch me moment. We’re just two girls from the deep-south after all! 

All of this to say: points are  for everyone — including you, Type B traveler who still loves chaos but doesn’t mind leveling up. We can still, stubbornly, embrace the chaos while making our money stretch.