The “Maxed-out” Hilton Strategy

Sharing my wife and I's 2-player "maxed-out Hilton" credit card strategy.

Over the years we've each accumulated 5 Amex Hilton Aspire cards through a combination of direct applications and upgrading from the surpass and hilton honors cards.

That's 10x Amex Hilton Aspire cards = $5500 annual fee total.

The Hilton Aspire cards give us 10 free night credits. We also put all our yearly credit card spend (around $60,000) on one of the cards to get an additional 2 free night credits. That's a total of 12 free night credits.

The Hilton Aspire cards give $400 in Hilton resort credits to offset their annual fee. So $4000 total available to spend on resort vacations every year.

That $4000 in spend also generates 34x points, so 136k points. Our $60,000 annual organic spend generates another 250k+ points, totaling ~380k-400k Hilton points every year.

The 12 free nights are used for luxury vacations (SLH or Waldorf Astoria properties) where rooms retail for $3000-4000 per night.

The $4000 in resort credits along with the ~400k hilton points are used up for vacations at at "mid-tier" luxury resorts, like the Conrad Maldives, retail price of $600-800 per night.

Overall we're getting about $50,000 in hotels spread across 4 vacations per year for $5500 in annual fees and $60,000 organic spend.

There are probably more complicated strategies that combine multiple hotel chains and point transfers that beat this, but we've found this works well for us and is pretty easy to manage.