Hilton points are valuable if you’re looking to take an aspirational trip to somewhere like the Maldives or Bora Bora. The Hilton portfolio of hotels includes the Conrad, Waldorf Astoria, and the Curio Collection.

The Hilton Honors American Express Aspire Card and the Hilton Honors American Express Surpass® Card  (after $15k spend) offer free weekend night certificates that you can use at almost any property.

Terms apply to American Express benefits and offers. Enrollment may be required for select American Express benefits and offers. Visit americanexpress.com to learn more.

Welcome Offer and Eligibility

American Express explicitly states in their credit card terms that you are not eligible for a bonus if you have or had a card.

“Welcome offer not available to applicants who have or have had this Card. We may also consider the number of American Express Cards you have opened and closed as well as other factors in making a decision on your welcome offer eligibility.”

The rule is not based on whether or not you received the welcome offer, but if you have or have had the specific card.

The Hilton Honors, Hilton Surpass, and Hilton Aspire cards are considered three different products. If you received a bonus for the Hilton Honors, you could still get a bonus for the Hilton Surpass.

Another example is if you opened the Hilton Surpass card, closed it after a week, and didn’t receive the bonus. You do not qualify for a new welcome offer because you had the card.

Being an authorized user on someone’s card does not disqualify you from getting the bonus yourself.

Upgrade Offers

Upgrade offers usually appear after having a card for at least 12 months. Due to the CARD Act, credit issuers cannot change the annual fee before the 12-month mark.

Another important note is that upgrade offers usually come with a minimum spend requirement.

Important: If you accept an upgrade offer, you must keep the card open for at least 12 months. Per the terms and conditions of the offer, Amex reserves the right to claw back the points or blacklist you.

Optimal Strategy

The optimal strategy for accumulating Hilton points and free night certificates is to get each Hilton product and upgrade them.

Triple Play Scenario

If you’re planning a vacation for 2021 or you’re looking to accumulate as many points and free nights as possible, the following timeline examples are ideal.

>> Feb 2020:

1. Hilton Honors = Intro Bonus #1
2. Hilton Surpass = Intro Bonus #2

>> Jun 2020:

       3. Aspire = Intro Bonus #3

Total = 3x Intro Bonus

>> Feb 2021:

1. Hilton Honors —> Hilton Surpass #2 = Upgrade Bonus #1
2. Hilton Surpass #1 —> Hilton Aspire #2 = Upgrade Bonus #2

>> March 2021:

        3. Hilton Surpass #2 —> Hilton Aspire #2 = Upgrade Bonus #3

Total = 3x Intro Bonus + 3x Upgrade Bonus

Big Upcoming Trip or Life Event Scenario

If you’re planning a vacation this year and looking to redeem points and certificates right away, then I recommend getting the Hilton Surpass and the Aspire for the weekend certificates.

>> Right now:

Hilton Surpass = Intro Bonus + weekend certificate after $15,000 in spend

>> Soon after:

Hilton Aspire = Intro Bonus + weekend night certificate

Edge Cases

If you want to be super aggressive, you could technically get all three Hilton products (Honors, Surpass, Aspire), and downgrade them all after 12 months to the no annual fee Hilton Honors.

You could then upgrade the cards to a Surpass, and then a second wave to Aspire cards. However, this scenario is not realistic for most people since the upgrade offers usually have a spend requirement.

Most people will not be able to spend $9,000 in three months to upgrade to the Surpass (x3), and then another $9,000 to upgrade to the Aspire (x3).

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