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Planning a Hawaiian Vacation with Hilton HHonors Points

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Hawaii lives up to the hype. There are plenty of award travel opportunities there, but today, TPG Senior Points & Miles Correspondent Nick Ewen looks exclusively at your options for using Hilton HHonors points in the 50th state.

Hawaii is typically a popular destination for award travelers. However, there are countless possibilities when it comes to accommodations on the islands. Which chain should you use? Should you visit just one island and/or one hotel? How long should you spend in each place? These questions naturally depend on factors like your flight details and how much vacation time you have, but in this post, I want to explore one idea for a Hawaiian vacation across three islands funded entirely with Hilton HHonors points.

Hawaii sunset beach featured shutterstock 162636074
If your travel plans include Hawaii, Hilton HHonors can help you stay for free. Image courtesy of Shutterstock.

Hilton HHonors currently has six “standard” properties in Hawaii where you can redeem points:

  1. DoubleTree by Hilton Alana Waikiki Hotel
  2. Embassy Suites Waikiki Beach Walk
  3. Hilton Hawaiian Village Waikiki Beach Resort
  4. Hilton Waikiki Beach
  5. Hilton Waikoloa Village
  6. Grand Wailea, A Waldorf Astoria Resort

Here’s a chart that shows how many Hilton HHonors points you’d need at each of these properties:

 Hotel Category January to April May June July and August September to November December
DoubleTree by Hilton Alana Waikiki Hotel 6 40,000 40,000 40,000 50,000 40,000 50,000
Embassy Suites Waikiki Beach Walk Distinctive Rewards 60,000 60,000 60,000 70,000 60,000 70,000
Hilton Hawaiian Village Waikiki Beach Resort 7 50,000 50,000 50,000 60,000 50,000 50,000**
Hilton Waikiki Beach 6 40,000 40,000 40,000 50,000 40,000 50,000
Hilton Waikoloa Beach 6 50,000 50,000 50,000 50,000 50,000 50,000
Grand Wailea, A Waldorf Astoria Resort 10 80,000* 70,000 80,000 80,000 80,000 70,000*

* Grand Wailea jumps to 95,000 points per night from December 21 – January 2.
**Hilton Hawaiian Village jumps to 60,000 points per night from December 21 – 31.

I’m of the opinion that any of these locations are a great spot to redeem your Hilton HHonors points, given that room rates tend to be relatively high in Hawaii. However, if you want to visit multiple properties across multiple islands to really make the most of your time, there’s an easy way to do so by taking advantage of few credit card sign-up bonuses between you and your travel companion:

  • Citi Hilton HHonors Reserve Card — Earn 2 weekend night certificates after making $2,500 in purchases within the first four months. You’ll also receive 10 points per dollar spent at Hilton properties; 5 points per dollar spent on airline and car rental purchases; and 3 points per dollar elsewhere. The card comes with automatic Gold status and no foreign transaction fees, though you’ll need to pay a $95 annual fee.
  • Hilton HHonors Surpass Card from American Express — Earn 100,000 points after you spend $3,000 in purchases on the card within your first three months. Earn 12 points per dollar spent at Hilton properties; 6 points per dollar spent at US restaurants, US supermarkets and US gas stations; and 3 points per dollar elsewhere. The card comes with automatic Gold status, but does carry a $75 annual fee.
  • Citi Hilton HHonors Visa Signature Card — For a limited time, this card is offering an increased sign-up bonus of 75,000 points after making $2,000 in purchases within the first three months. The automatic Silver status isn’t as generous as what’s offered on the two cards above, but this one has no annual fee.
Citi Hilton cards
These two cards can play a big role in earning free nights at Hilton properties.

Suppose you and your companion each sign up for these three cards and meet the minimum spending requirements to earn the bonuses. You also put all dining, grocery and gas purchases on the Surpass card (to earn 6x points). You would each earn the following haul of points:

  • Citi Hilton Reserve — 2 free weekend nights + 7,500 points ($2,500 x 3 points/$)
  • Hilton Surpass — 60,000 bonus points + 18,000 points ($3,000 x 6 points/$)
  • Citi Hilton Visa — 75,000 bonus points + 4,000 points ($2,000 x 2 points/$)
  • TOTAL — 2 free weekend nights plus 164,500 points each

Each person’s combined haul of points is worth $822.50 based on TPG’s most recent valuations, though that doesn’t take into account the potential value of your free night certificates. However, by planning your vacation strategically, you can get almost two weeks of vacation through these points alone. Here’s how this would work in the months of January – June and September – November (looking mainly at 2016, since availability is much better after the first of the year):

You can enjoy spectacular sunset views over the reflection pool at the Grand Wailea
The Grand Wailea on Maui is a great use of your free night certificates.

Use Three of your Four Certificates at the Grand Wailea

Your vacation starts on the island of Maui. As I discuss in my post on Maximizing Citi Hilton Reserve Free Nights, you can use these certificates on Friday, Saturday or Sunday nights. Since Grand Wailea has the highest award redemption requirements (and cash rates of at least $500 per night), this is your best option for using the free night certificates. You’ll need to find standard award room inventory, so look for rooms using Hilton points that price at 70,000 – 80,000 points per night.

This property actually made my list of 8 Hilton properties that make for awesome award redemptions, and for good reason. The resort is nestled on 40 acres of tropical gardens on Wailea Beach, and offers luxury beachfront accommodations and numerous activities to keep the whole family busy. Kids and teens will love the Wailea Canyon Activity pool, with its multiple levels and several slides, waterfalls and Jacuzzis, while adults can escape to the Hibiscus pool. The property boasts eight restaurants and bars plus the Spa Grande (voted one of the top 10 spas in the US by Conde Nast Traveler).

You can enjoy spectacular sunsets at the Hilton Waikoloa Village on the big island of Hawaii.
You can enjoy spectacular sunsets at the Hilton Waikoloa Village on the big island of Hawaii.

Book a Four-Night AXON Stay at the Hilton Waikoloa Village

The next stop on your trip is on the big island of Hawaii for a four-night stay at the Hilton Waikoloa Village, which actually ranks as the second most popular redemption by Citi Hilton cardholders. Four nights may seem like an arbitrary length, but it allows you to take advantage of Hilton’s updated AXON awards, available exclusively to holders of a co-branded Hilton American Express card. These used to be quite attractive redemption options, but with the massive devaluation of 2013 and the introduction of seasonal pricing, they lost some of their appeal. Still, there is value to be had, and a high-priced Category 6 property like the Hilton Waikoloa Village is one sweet spot.

A four-night stay in a Category 6 property would normally set you back anywhere from 120,000 – 200,000 points (depending on when you visit). A four-night AXON stay is a fixed price of 160,000 points. This means that you’re best off redeeming this award when a property normally charges 50,000 points per night. It just so happens that the Hilton Waikoloa Village fits the criteria, so you (or your companion) can use your points for four nights. Just about every date in 2016 has availability, with paid room rates starting at $199 per night.

Situated on the Kohala Coast just 20 minutes from Kona International Airport, the property provides a wide range of amenities to keep you busy yet relaxed throughout your stay. Recreational activities include two championship golf courses, eight tennis courts and three swimming pools, while each of the 1,240 guest rooms includes a balcony with ocean or garden views. Dining options include 14 restaurants and lounges, while the Kohala Spa and meditative gardens help you while the days away. If you don’t feel like traversing the 62 acres on foot, you can grab an air-conditioned tram or canal boat to whisk you around the property.

Both the DoubleTree and Hilton are just off Oahu's famous Waikiki Beach.
Both the DoubleTree and Hilton are just off Oahu’s famous Waikiki Beach. Image courtesy of Shutterstock.

Book a Five-Night Stay at the Hilton Waikiki Beach or DoubleTree Alana Waikiki

The final part of your vacation brings you to the island of Oahu. Here, you actually have two options: the Hilton Waikiki Beach or the DoubleTree by Hilton Alana Waikiki Hotel. Both of these properties are classified as Category 6, yet they only require 40,000 points per night from January to June and September to November. Since Hilton gives elite members the fifth night free on all award redemptions, a five-night stay at either of these hotels will only set you back 160,000 points. Both have wide-open award availability, with paid rates starting at $209 per night.

The DoubleTree is situated just off Waikiki Beach and boasts many amenities and services for guests, including a heated outdoor pool and on-site restaurant. The 317 guest rooms and suites all feature private lanais with partial ocean or mountain views. The hotel is actually the sister property of the Hilton Hawaiian Village and is located just a block away, giving you access to a multitude of additional activities. You can also stroll to the Ala Moana Center, the largest open-air shopping center in the world.

The Hilton Waikiki Beach is in the heart of Waikiki, though still just a block from the ocean. You can walk to numerous restaurants and popular tourist attractions, including the Honolulu Zoo and Kapiolani Park. All of the rooms provide city, mountain or ocean views, and are furnished with contemporary decor and vibrant island colors. You can also grab a bite any time of day at the aptly named MAC 24/7.

You can book inter-island flights on Hawaiian Airlines using a variety of mileage currencies.
You can book inter-island flights on Hawaiian Airlines using a variety of mileage currencies.

Other Redemptions for a Hawaiian Vacation

Free nights aren’t the only way to redeem your Hilton HHonors points. You can also transfer them to a variety of airline partners that can help you get to (or around) the islands. Generally speaking, this is a very poor redemption value, but if you’d rather keep the money in your pocket, it might make sense in certain situations.

You have five transfer options for redemptions on inter-island flights, all of which are operated by Hawaiian Airlines:

  • Hawaiian — 7,500 miles one-way per person, which requires 50,000 Hilton HHonors points
  • Delta — 7,500 miles, which requires 80,000 Hilton HHonors points
  • United — 6,000 miles, which requires 60,000 Hilton HHonors points
  • American — 5,000 miles, which requires 40,000 Hilton HHonors points (though this option will be going away as of September 1, 2015)
  • Virgin America — 3,000 miles, which requires 30,000 Hilton HHonors points

While Virgin America is the clear winner, this is still a poor use of Hilton points. These one-way flights are often less than $100, so by transferring points to Virgin America, you’d still only get about 0.3 cents per point in value.

Important Caveats

While the strategy I outlined above can work for anyone, it’s not a foolproof plan to get a free trip to Hawaii. Keep the following tips in mind:

  1. Book in advance — I’m always amazed when friends ask me to help them find availability at luxury hotels just a few weeks in advance. Three of the top four most popular redemptions by Citi cardholders were in Hawaii, so you’re unlikely to score a great redemption there at the last minute. That said, availability for most properties (especially the Grand Wailea) is currently good for 2016.
  2. Beware of Citi application restrictions — You’re only allowed to apply for one Citi card every 8 days, and you won’t be approved for more than two Citi applications within a 65-day period. As a result, you’ll want to space out your applications for the two Citi Hilton cards.
  3. Consider switching the order of stays — The above itinerary is just a sample of what you can do, and the order in which you visit the islands really doesn’t matter. The only thing you’ll want to be sure of is that you plan the Maui portion of your trip on a weekend so you can use the free night certificates.

Bottom Line

Hawaii is a dream destination for many award travelers, whether for a honeymoon, anniversary or just a memorable vacation. If you’re planning a trip to the Aloha State, Hilton HHonors can help you cover a big chunk of your cost.

For more on award travel to Hawaii, check out these posts:

Have you redeemed Hilton points toward your Hawaiian vacation?

Citi® Hilton HHonors™ Reserve Card

Apply Now
  • Earn 2 weekend night certificates good at select hotels and resorts within the Hilton Portfolio after you make $2,500 in purchases within 4 months of account opening*
  • Earn 10 Hilton HHonors Bonus Points per $1 spent on hotel stays within the Hilton Portfolio*
  • Earn 5 Hilton HHonors Bonus Points per $1 spent on airline and car rental purchases*
  • Earn 3 Hilton HHonors Bonus Points per $1 spent on all other eligible purchases*
  • Enjoy the benefits of HHonors Gold status as long as you are a cardmember*
  • No foreign transaction fees on purchases*
  • Travel with ease and enjoy global acceptance with your Citi chip credit card
Intro APR Regular APR Annual Fee Foreign Transaction Fee Credit Rating
N/A 15.49% (Variable) $95 0% Excellent Credit