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Cleared for Takeoff: Booking a second Honeymoon in Hawaii

Aug. 10, 2021
13 min read
Hawaiian 717 Takeoff Honolulu wing view
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Cleared for Takeoff is a weekly series showing readers like you the best ways to book adventures using points and miles. If you’d like tips on booking your own trip using miles, please email us with your preferred itinerary and current mileage balance.

For the past year and a half, travel has been as unpredictable as it gets. The coronavirus pandemic hit all of our travel plans hard and we've seen wildfires ravaged many tourist destinations throughout the West Coast. This is in addition to hurricane season and other annual mishaps that affect travel plans for even the most seasoned travelers.

So in this episode of Cleared for Takeoff, we'll help reader Robert Heaser and his wife plan part two of their rescheduled honeymoon:

"My wife and I are hoping to have a honeymoon part 2 in Hawaii sometime in late 2021 or 2022. Our first attempt was stymied by COVID and wildfires! We are looking to fly out of any of the airports in the Washington DC area. We have 150,000 Amex Membership Reward points and are seeking help redeeming them optimally."

While Robert doesn't have the biggest points stash to work with, I should be able to get him and his wife to Hawaii with his stash of American Express Membership Rewards points. I'll also provide a couple of recommendations that can help him book his hotels on points too.

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Points stash

As discussed in the intro, Robert only has American Express Membership Rewards points. Thankfully, he has a sizable stash of these points and they're very flexible, making it easy for him to find a great flight. Remember, Amex points transfer to a number of different airline and hotel loyalty programs.

  • 150,000 American Express Membership Reward points

Of course, here at TPG, we always recommend that you diversify your points and miles portfolio. I'll discuss some ways he can do this as we move through the article.

Related: Better together: An ultimate guide to the best credit card pairings

Airfare to Hawaii

Robert and his wife can fly United to Hawaii with their Amex points. (Photo courtesy of Ryan Patterson/The Points Guy)

Robert gave us a wide date range for his second honeymoon to Hawaii — he and his wife are open to traveling in late 2021 or any time in 2022. This works to his advantage as it lets him search for a broad range of award space. Award availability to Hawaii is notoriously hard to come by, so this could make the difference in him finding a great award ticket.

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The pair are based in Washington D.C., so I'll focus on programs that offer reasonable prices on flights from the East Coast to Hawaii. We will use Honolulu (HNL) as the destination for this search as it's a great city close to a slew of beaches on Oahu. Plus, it's an easy jumping-off point to other Hawaiian islands.

One of the best ways to book award flights from the mainland U.S. to Hawaii is using Singapore Airlines Krisflyer to book flights on United Airlines. You'll pay just 35,000 points round-trip in economy and 69,000 in business class. You can transfer Amex points to Singapore Airlines at a 1:1 transfer ratio.

We're seeing solid award space in March 2022 for flights from Washington-Dulles (IAD) to Honolulu (HNL). This includes flights on United's non-stop flight between the two cities.

(Screenshot courtesy of

This is hands-down the best way for Robert and his wife to fly to Hawaii for both convenience and points price. If Robert and his wife book two round-trip economy tickets, they will spend 70,000 Amex points and have 80,000 left for future redemptions.

How to book this award with points

You can book United awards with Singapore Krisflyer miles on the Singapore Airlines website. Just head over to the Singapore website, log in and enter your search criteria at the center of the screen. Click the "Redeem flights" radio button to view award flights to search for award tickets.

(Screenshot courtesy of

Now, look toward the top of the screen and click the "Star Alliance" option to view United flights. You can use the weekly calendar below this button to view flight availability for the dates surrounding the day you searched. You can view more dates by clicking the arrow buttons to the left and right of the calendar. Any date with a price has open award space.

(Screenshot courtesy of

Click on the date you'd like to book and you'll see all available flight options at the center of the screen. If you see a flight you'd like to book, start your points transfer. Once the points are in your account, re-run the search, click on the flight you'd like to book and follow the on-screen prompts to process your ticket.

(Screenshot courtesy of

One thing to note: Singapore transfers from Amex take roughly 24 hours to process. Have a backup flight in mind in case someone books your preferred flight before your points transfer. You can also call Singapore Airlines and ask a phone agent to put your award on hold, but whether or not you can hold a partner flight largely depends on the agent you speak with.

How to earn enough miles for this award

Interested in booking this for yourself? Consider opening an American Express card to build up your own stash of Membership Rewards points. You can emulate Robert's trip to Hawaii or book any one of these other great Membership Rewards sweet spots. Here's a look at the best Amex offers:

  • American Express® Green Card: Earn 60,000 Membership Rewards points after you spend $3,000 on purchases within the first six months of card membership. Plus, 20% back on eligible travel and transit purchases in the first six months, up to $200 back in the form of a statement credit. Earn 3x points at restaurants, travel and transit, 1x points on all other purchases, $150 annual fee (see rates and fees).
  • American Express® Gold Card: 60,000 points after you spend $4,000 on eligible purchases with your new card within the first six months of account opening. Earn 4x points on dining at restaurants; 4x points at U.S. supermarkets (up to $25,000 per calendar year; then 1x points); 3x points on airfare purchased directly from airlines; 1x points on all other purchases, $250 annual fee (see rates and fees).
  • The Platinum Card® from American Express: 80,000 Membership Rewards® Points after spending $6,000 on purchases on the Card in your first 6 months of Card Membership. Earn 5x points on airfare purchased directly from airlines or Amex Travel (on up to $500,000 on these purchases per calendar year, starting Jan. 1, 2021), 5x hotels booked through Amex Travel and Amex Fine Hotels & Resorts; 1x on all other purchases, $695 annual fee (see rates and fees).

Related: The best ways to get to Hawaii using points and miles

Hotels in Honolulu and Maui

Unfortunately, Robert doesn't have any hotel points to redeem on his trip. Amex Membership Rewards can transfer to three hotel programs — Choice Privileges, Hilton Honors and Marriott Bonvoy — but it's rarely a good deal. This is in large part because most hotel points have low valuations compared to transferable points.

So with that in mind, Robert and his wife may want to consider open new cards that focus on earning World of Hyatt points. Robert told TPG that he already has a Chase Sapphire Reserve, but was unclear on how many points he has. With that in mind, Robert may want to apply for a World of Hyatt Credit Card and his wife may apply for a Chase Sapphire Preferred Card since Chase Ultimate Rewards points transfer 1:1 to World of Hyatt.

If they can both earn the full signup bonuses for their respective cards, they'll end up with 60,000 World of Hyatt points and 60,000 Chase Ultimate Rewards points after reaching the minimum spending requirements. Plus, Robert would earn a free night certificate good at any Category 1-4 Hyatt property after spending $15,000 on his World of Hyatt card to meet the full signup bonus.

If the couple wanted to split their trip between Honolulu and Maui, they could use 60,000 points for three nights at the Hyatt Regency Waikiki Beach Resort and Spa. This hotel is located right off Waikiki Beach and has an on-site spa, beach access and modern rooms. It's a great place for them to spend their first few nights in the Aloha State.

Hyatt Regency Waikiki Beach Resort. (Photo courtesy of Hyatt)

Then, the couple could jet to Maui and spend three nights at the luxurious Andaz Maui for 90,000 points. This property frequently costs well over $800 per night and is one of Hyatt's premier properties in the Hawaiian islands. The property is set on 15 acres of beaches and features excellent dining and spa amenities.

The Andaz Maui at Wailea Resort. (Photo courtesy of Hyatt)

How to book a Hyatt hotel with points

To book a Hyatt hotel, head to the Hyatt website and enter your itinerary at the center of the screen. Make sure to check the “Use Points” box to see award pricing.

(Screenshot courtesy of Hyatt)

Find the hotel you’d like to book and click “View Rates” to see available award rooms. You may have to play around with dates when booking high-demand hotels, as award availability can dry up quickly. This is especially true for properties like the Andaz Maui that are often in high demand.

(Screenshot courtesy of Hyatt)

Select the room you’d like to book and follow the on-screen prompts to complete your reservation.

(Screenshot courtesy of Hyatt)

Related: 9 mistakes to avoid when redeeming hotel points

How to earn hotel points

The easiest way to earn World of Hyatt points is by transferring them in from Chase Ultimate Rewards. As discussed, Chase points transfer to Hyatt instantly at a 1:1 transfer ratio. If you're interested in earning Chase points for your next Hyatt booking, consider applying for one of these Chase cards:

  • Chase Sapphire Preferred Card: Earn 60,000 bonus points after spending $4,000 on purchases in the first three months from account opening. Earns 3 Ultimate Rewards points per dollar on dining and 2 Ultimate Rewards points per dollar on travel purchases.
  • Chase Sapphire Reserve: Earn 60,000 bonus points after you spend $4,000 on purchases in the first three months from account opening. Earn 3 Ultimate Rewards points per dollar on travel and dining purchases.
  • Ink Business Preferred Credit Card: Earn 100,000 bonus points after you spend $15,000 in the first three months from account opening. Earn 3 Ultimate Rewards points per dollar on the first $150,000 spent per calendar year (then 1 point per dollar) on shipping, internet, cable, phone, advertising with social media sites and search engines and travel.

Alternatively, you can open a Hyatt cobranded credit card:

  • World of Hyatt Credit Card: Earn 30,000 bonus points after spending $3,000 on purchases within the first three months from account opening. Plus, up to 30,000 more bonus points by earning 2 bonus points total per $1 spent on purchases that normally earn 1 Bonus Point, on up to $15,000 in the first six months of account opening.

Related: How to redeem Chase Ultimate Rewards points for maximum value

Bottom line

In this article, I showed Robert and his wife how to book a Hawaiian honeymoon with points and miles. Robert has more than enough points to fly to Hawaii but needs to stock up on hotel points to book hotels if he wants to offset hotel costs. This is a perfect example of why it's always a good idea to diversify your points portfolio to include multiple points currencies.

Have a destination in mind and need help figuring out your points strategy? Send us an email to be featured in the next installment of Cleared for Takeoff.

For rates and fees of the Amex Green card, click here.
For rates and fees of the Amex Gold card, click here.
For rates and fees of the Amex Platinum card, click here.

Feature photo by Ryan Patterson/The Points Guy

Featured image by (Photo by Ryan Patterson/The Points Guy)
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.