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.
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.
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.
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.
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.