My picks for aspirational Hilton stays

TL;DR. Apply for the Citi Hilton HHonors Reserve card for two free nights at one of the grand daddy Hilton properties covered in this post: Hilton Bora Bora, Conrad Maldives, Hilton Seychelles, Hilton Queenstown, Grand Wailea, Conrad Koh Samui

Once upon a time (long ago before their massive devaluation), I came into hundreds of thousands of Hilton points.  I bank rolled most of these points by actually staying at Hiltons on lucrative bonus point stays. There are definitely credit card strategies out there, but thought I’d first tempt you with some of my favorite properties in the Hilton portfolio for award stays.

Aspirational properties for Hilton Award Stays 

Upon review of my list, I realized that I’ve pretty much exclusively chosen waterfront Hilton properties. By design, I sought out the most expensive Hilton properties for my award stays. It just so happens that all of those properties ended up being beach front. And while I’ve stayed at Conrads and Hiltons in Singapore, Sao Paulo, San Francisco, Buenos Aires and Barcelona, I generally find Hilton’s city properties to be sub-par.

Hilton Bora Bora, French Polynesia. I always thought a white sand beach was a white sand beach no matter how lovely the palms fringing the island were. But Bora Bora is in a class all on its own and while service and food are at the Hilton leave a lot to be desired, when you’ve got an overwater bungalow and the most pristine azure waters at your back door, what else do you need.

We paid $100 per night to upgrade to one of those overwater bungalows you see off in the distance

We paid $100 per night to upgrade to one of those overwater bungalows you see off in the distance

This photo is not edited in any way.

This photo is not edited in any way.

Conrad Maldives. I visited this property in 2009, sent my parents here for their 31st anniversary, and will be returning with Rob at the end of November. If if I knew what I knew now, I would’ve sent my parents to Bora Bora. That said, the food and the service at the Conrad were better and we had no trouble filling out days with a lot of (expensive) nothing.

Enjoying lunch from the spa restaurant

The property is distributed across two islands and connected by a long walk bridge (which is patrolled by a manta in the evenings!). If you don’t fancy walking, you could always wait for the dingy to transport you.

Hilton Seychelles. Every meal (off property) we had in the Seychelles was stellar–from the beach shack curries to the well guarded lasagna recipe from Napoli. My favorite part of this hotel were the rooms, which were not only huge, but also sultrily dressed in dark woods and warm lighting. The beach was small and rocky though.

Hilton Queenstown. A relatively new hotel set directly on the shore of Lake Wakatipu. The staff was superb. Breakfast was a generous spread. And the Relaxation Rooms come with your own personal hot tub. ‘Nuff said.

The Relaxation Rooms come with a private hot tub

The Relaxation Rooms come with a private hot tub


Grand Wailea, Maui: A Waldorf Astoria Resort  that’s great for kids. The rooms weren’t anything to write home about, but the on-premise water park is sure to be a crowd pleaser for the entire family.

The view was the best part of our room at the Grand Wailea

With the water slides, lazy river and waterfalls making for fun for the whole family

Conrad Koh Samui. I had originally targeted this property as my last hurrah for my Hilton points, when my cousins gave me lukewarm reviews. I had to make a call before my Hilton points loss 50% of their value, so I opted for the Maldives a second time. I’ve still got one more free night certificate, so may get around to enjoying the private infinity pool after all.

Courtesy of


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s