Should I Get the AMEX Hilton Aspire card? Part 4: Maximize Points Redemptions at Top Hilton Hotels



Grand Wailea, A Waldorf Astoria Resort

Previous posts:

New Hilton American Express Credit Cards FAQs: Points Bonus, Elite Status, Lounges, and More

Should I Get the AMEX Hilton Aspire card? Part 1: $250 Resorts Credit Detailed Review

Should I Get the AMEX Hilton Aspire card? Part 2: What Are Hilton Honors Points Worth in the Americas and Europe?

Should I Get the AMEX Hilton Aspire card? Part 3: What Are Hilton Honors Points Worth in Asia, Africa and the Middle East?

This is the final part of my long-winded American Express Hilton cards saga, which is dedicated to one thing only: optimizing your Hilton Honor points to make them go further.

In my previous installments, I covered Hilton Honors’ sweet spots and the American Expres cards you can apply for to get there. We’ve also touched on how you can use these credit card benefits to your advantage. We’ve discussed which Hilton hotels you’re better off booking on cash rather than points. And we mostly covered the cheapest (but still interesting) locales with a simple goal in mind – to maximize our travel time.

This final part throws it all out the window. It’s about aspirational travel and staying at top Hilton hotels. No more cheap stays, and no maximizing your travel time. This is about how to blow up hundreds of thousands of Hilton Honor points in one sitting and – get this – do it wisely.  🙂 

You’ll see that a lot of top Hilton hotels didn’t make it to this list. If you go to a big city, you have a lot of lodging choices, and rarely, if ever, will a big-city property also be your aspirational “destination hotel.”

Besides, since I value Hilton points around $0.005, that hotel room had better cost around $475 or more to justify (theoretically) the top 95,000-point rate.

Reminder: when you’re planning a stay at one of these top Hilton hotels, try to stay 5 nights to get the 5th night free benefit for elite members (and if you’re staying 10 nights, book 2 stays). Also, keep in mind that all rates are valid at the time (and even hour) of writing. Hilton prices and rates always fluctuate, so do your own research. You might have a somewhat different experience.

The U.S.

DoubleTree Suites by Hilton Hotel New York City – Times Square 53K-95K

top Hilton hotels

DoubleTree Suites by Hilton Times Square-New York City: from 53,000 points

The location is unbeatable; the rooms are your world-famous New York size. 53,000 points a day for a 5-day stay – yes; 95,000 – no way!

Waldorf Astoria Chicago 67K-95K

top Hilton hotels

Waldorf Astoria Chicago: from 67,000 points

This is a stunning hotel and and architectural jewel, so if you can make your stay in Chicago special and can get a room around 70,000 points, it’s not too terrible (remember, Gold and Diamond members get free breakfast now at Waldorf Astoria). The problem is, though, that the hotel has blocked all availability from June to November at this point, at least on the Hilton website. So… there is that.

Maui: Grand Wailea, A Waldorf Astoria Resort 95K

top Hilton hotels

Grand Wailea, A Waldorf Astoria Resort: 95,000 points

The Hilton site is often glitchy when you’re searching the dates for this hotel, and it sometimes shows no availability at all. When it’s not glitchy, I’ve found there is not a single day in a year that costs less than 95,000 points. This is an incredible hotel with amazing beach and gorgeous grounds, if  the points are not an issue and you can find availability.


Hilton Reykjavik Nordica 41K-60K

top Hilton hotels

Hilton Reykjavik Nordica hotel: from 41,000 points (Executive Lounge)

This is not an aspirational hotel, but Iceland is an aspirational country. And very expensive too, for both lodging and food. You know it’s something when the locals tell you “Eh, but it’s even worse in Norway.”

This Hilton has a very nice spa and an executive lounge that serves snacks in the evening. I don’t know if these snacks can replace dinner, but having it as an option can’t hurt.


Waldorf Astoria Amsterdam 81K-95K

top Hilton hotels

Waldorf Astoria Amsterdam

Remember I said big city properties rarely double as “destination hotels”? This Waldorf Astoria seems to be not just one of the top Hilton hotels, but also one of the rare exceptions. Incorporating several 17th century palaces, the hotel features every luxury in the book including a personal concierge.

However, I’ve failed to find 5 consecutive days available from spring to fall to justify the 95,000-points rate. If you want to travel to the Netherlands in or after November, you can have it for (start laughing) 93,000 points a night, but you might want to be prepared to spend most of your time inside if the weather doesn’t cooperate. Which, admittedly, shouldn’t be too difficult because the place is truly fabulous.

Or, for a really special vacation, go to Amsterdam on a Christmas week or New Year’s Eve. I was a bit surprised to find availability wide open for that time of the year.

top Hilton hotels

Christmas and New Year’s Eve are wide open


Gran Hotel Montesol Ibiza, Curio Collection by Hilton 52K-95K

top Hilton hotels

Gran Hotel Montesol Ibiza, Curio Collection by Hilton: from 52,000 points

If you have to go to famed Ibiza to see what it’s all about, staying here will likely cost you 380,000 points for 5 days. Why? Because you don’t want to go to Ibiza in winter, or spring, and, unfortunately, every day between June and September costs 95,000 points at this hotel. Now, Octobers are still warm in Ibiza, so you can save a little, but you will still pay 88,000 points per night.


Conrad Ko Samui 95K

top Hilton hotels

Conrad Koh Samui: 95,000 points

OK, been there, done that. Unfortunately, I haven’t found a single date that would cost less than 95,000 points. Is it worth it? Everyone knows about this unique resort featuring ocean-view villas with private pools, and as a once-in-a-lifetime experience, I’d have to say yes. Then again, in 2013, I paid only 145,000 Hilton points for my 5-night stay, and not the 380,000 points it would cost you now for the same experience. Gee, time flies even faster in the “loyalty” world, doesn’t it?


Hilton Moorea Lagoon Resort & Spa 80K

top Hilton hotels

Hilton Moorea Lagoon Resort & Spa: 80,000 points

If you want a shot at getting upgraded to an overwater bungalow, try to stay here. Yes, Hilton also has ultra-luxury properties on Bora Bora and in the Maldives, but I’ve only found a couple of available dates on Bora Bora (and the Maldives are never below 95,000 points). If you must have this experience, try to get Hilton Moorea first.


Hilton Seychelles Labriz Resort & Spa 80K

top Hilton hotels

Hilton Seychelles Labriz Resort & Spa: 80,000 points

Hilton also has another property in the Seychelles – Northolme Resort & Spa – but that one goes for 95,000 points every day of the year (again, at the time of writing). The Labriz costs 80,000 points a day, and if you’re a Diamond, you might have a shot at upgrading to the beach villa with a private pool.


Hilton Odawara Resort & Spa 38K-95K

top Hilton hotels

Hilton Odawara Resort & Spa: from 38,000 points

Would I spend 95,000 points a night there? No, but this amazing onsen (spa) resort can be a good buy if you find a room at the cheaper end of the spectrum. Reportedly, there isn’t much to see and do around the town (and the resort is a bit away from the town in the first place), but this property is perfect to relax and unwind in the onsen, or one of several uniquely-designed swimming pools. Odawara is just a 35-minute train ride away from Tokyo, which makes it a great overnight or weekend trip.

How to search for a room

The Hilton website has a nasty habit of kicking you out when it thinks you’ve overstayed your welcome. It won’t tell you anything; rather it will just freeze your search while you’re clicking around not knowing what’s just happened. If you’re doing an extensive research of your rewards options, use these tricks:

  • Always search anonymously, e.g. in Chrome Incognito. Don’t log on, it won’t change a thing (you know you’re getting the 5th night free anyway if you have a Hilton credit card).

  • When they freeze you (and they will, eventually) close your Incognito window, go back to your regular browser, and open the Incognito window again. It’s that easy!

Is this list of top Hilton hotels exhaustive?

Of course not! Just treat it as yet another suggestion of what you can do with your Hilton points. There are other aspirational Hilton properties around the world you might enjoy, and, if you have any personal experiences, please share them in the comments.


One Response to Should I Get the AMEX Hilton Aspire card? Part 4: Maximize Points Redemptions at Top Hilton Hotels

  1. […] The final post in the series about best values with Hilton after getting their new Amex Hilton Honors cards. In this post we learn about how to maximize Hilton Honors points in top Hilton family hotels. […]

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