Cleared for Takeoff: A honeymoon trip to the Maldives on points and miles

Aug 24, 2021

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Cleared for Takeoff is a weekly series showing readers like you the best ways to book post-pandemic 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.

The Maldives is the ultimate bucket list destination, so it’s not surprising that we get a lot of Cleared for Takeoff requests for trips to this chain of islands. For example, we recently helped TPG readers Ray and Nicole Saylor book their Maldivian overwater villa dream vacation and reader Oz Noori book a mother-daughter getaway to paradise. Today, we’ll look into reader Brian Frank’s request for help planning a honeymoon to the Maldives for himself and his wife-to-be:

Hello TPG & Team – I was hoping you’d be able to provide me some tips on booking my Honeymoon with my lovely fiancée & wife-to-be.  Feel free to publish this on your website!

Keeping it short and sweet, here are my point balances and preferred details:

Preferred Details:
Destination: Bora Bora or Maldives (Flying from Chicago)
Dates: Leave May 10 – 12, 2022 from ORD and return May 18 – 22 to ORD
Fare Class: Business (Y) or First (F)
7 days at the resort, with 2-3 days on top of that allocated for travel (as I know Maldives is 5-10 hours more of travel time than Bora Bora)
Resort with higher quality food, and an overwater bungalow. We are open to beach bungalows as well, depending on what fits our point balances

We are also open to staying overnight in Tahiti or Dubai for a night if it works better for the bookings. Thank you so much in advance.

Although Brian is also open to Bora Boral, the Maldives seems to be a better fit based on his points balances and requests. They’ll have more options with Marriott Bonvoy in the Maldives and have lots of ways to fly there on points.

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In This Post

Current points stash

Brian and his fiancé are off to a great start teaming up on a credit card strategy as a couple.

Together they have a healthy mix of Chase Ultimate Rewards, American Express Membership Rewards, Citi ThankYou, American Airlines, Marriott Bonvoy, Hilton Honors and IHG Rewards points. They also have several free night rewards and other travel credits.

  • 230,000 Chase Ultimate Rewards points (Brian)
  • 125,000 Chase Ultimate Rewards points (fiancé)
  • 70,000 American Express Membership Rewards points
  • 60,000 Citi ThankYou points
  • 70,000 American Airlines AAdvantage miles
  • 70,000 Marriott Bonvoy points (Platinum Elite)
  • 3x Marriott Bonvoy 50,000-point free night certificates
  • 70,000 Hilton Honors points
  • 70,000 IHG Rewards points
  • 1x IHG 40,000-point reward night certificate
  • $1,000 United Electronic Travel Certificate (ETC)

They noted that they currently hold cards like the Chase Sapphire Reserve, Marriott Bonvoy Boundless Credit Card, Citi® / AAdvantage® Platinum Select® World Elite Mastercard®, American Express® Gold Card and IHG Rewards Premier Credit Card.

Plus, they shared that they’re willing to open more travel credit cards to further boost their rewards balance. Some cards they’re considering include the Capital One Venture Rewards Credit Card, United Explorer Card, Marriott Bonvoy Brilliant™ American Express® Card and the Citi® / AAdvantage® Executive World Elite Mastercard®.

The information for the Citi AAdvantage Platinum card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Airfare to the Maldives

Route: Chicago-O’Hare (ORD)- Doha (DOH) – Male (MLE)

Miles needed: 70,000 miles + $15.70 per person

There are many ways to get to the Maldives on points and miles, but perhaps the most comfortable business class option is with Qatar Airways via Doha (DOH). Most Qatar flights between the U.S. and Doha feature Qatar’s Qsuites so Brian and his fiancé will want to reserve the couple-friendly seats in the middle of the plane which can be converted into a double bed for two.

Lucky for Brian, he already has the exact amount of miles to book one of these tickets through American Airlines AAdvantage. Taxes and fees are very reasonable at under $20 per person.  Brian’s fiancé will be able to earn the miles she needs by picking up a cobranded American Airlines credit card.

Related: Maximizing redemptions with American Airlines AAdvantage

(Photo by Benji Stawski/The Points Guy)

How to book this award with points

You can book Qatar Airways flights with AAdvantage miles directly through American’s website. Head to, enter your route (in this case, ORD-MLE), select your dates and check off the “Redeem miles” box.

(Screenshot courtesy of

On the next page, you’ll see a list of all of the available flight options for the date you selected. If there are no flights that work for you, there’s a handy calendar search tool you can use. You can also use ExpertFlyer (owned by TPG’s parent company, Red Ventures) and set alerts to be notified when award space opens up. Also, be sure to review the details of your flights to make sure you’re not booking a mixed cabin itinerary.

QR Award Availability ORD-MLE
(Screenshot courtesy of

After you’ve selected your flights, you’ll need to log in to your AAdvantage account to complete the booking. The business class ticket will cost 70,000 miles regardless of where in the U.S. you’re departing from and the taxes and fees on this ticket should come out to around $20 per person.

How to earn enough miles for this award

As mentioned, Brian only has enough AAdvantage miles to book one of these tickets. And unfortunately, there aren’t a ton of ways to transfer miles into AAdvantage, though there are more than there used to be.

One transfer option is via Marriott Bonvoy. Points transfer at a 3:1 ratio to most airlines, and you’ll get a 5,000 mile bonus for every 60,000 points you transfer. This means 60,000 points is worth 25,000 AAdvantage miles.

Finally, you can transfer Bilt Rewards points to AAdvantage at a 1:1 transfer ratio. This is a relatively new points program that rewards members for paying rent every month. Points transfer to a handful of airline and hotel points programs, including World of Hyatt.

Editor’s note: TPG founder Brian Kelly is a Bilt advisor and investor.

Another solid option is to pick up a cobranded American Airlines credit card. In particular, here are some cards to consider (and their current bonuses):

The information for the CitiBusiness Platinum Select, AAdvantage Aviator Red and the AAdvantage Aviator Business cards has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Related: Should you pay your rent with this new credit card? We crunch the numbers

Airfare from the Maldives

Route: Male (MLE) – Chicago-O’Hare (ORD)- Doha (DOH)

Miles needed: 117,500 miles + $291.95 per person

For the return, I recommend Brian and his fiancée book Emirates business class via Dubai (DXB). While Emirates doesn’t offer the most private business class seats, it’s still a great product overall and if they end up on an A380, they’ll have access to the famous in-flight bar area.

Emirates charges a bit more miles than American for this route, but the awards are much easier to book thanks to the Skywards program’s many transfer partners.

Related: The best programs for booking Emirates awards

(Photo by Samantha Rosen/The Points Guy)

How to book this award with points

The beauty of Emirates awards is how easy they are to book. While you can book Emirates awards through several programs, I recommend Brian books directly through the carrier’s own Skywards program. This is because it’s a transfer partner of all transferable points programs, allowing Brian to mix and match his Amex, Chase and Citi points.

To book these awards, log in to your Emirates Skywards account. Then, you’ll be able to search for flights as you normally would through Emirates’ homepage but check the box that says “Classic rewards.” In this case, we’re searching for two business class tickets from MLE to ORD.

(Screenshot courtesy of

On the next page, you’ll see the rates for each of the flights available. You must have enough points in your account to book to be able to progress past this page.

(Screenshot courtesy of

The award should come out to 117,500 miles and about $292 in taxes and fees. Be sure to pay using a card like The Platinum Card® from American Express or Chase Sapphire Reserve. Not only do they earn bonus points on airfare, but they offer perks like trip delay reimbursement and trip cancellation and interruption protection, which can be lifesavers when things go wrong.

Related: The best credit cards for paying taxes and fees on award tickets

How to earn enough miles for this award

As a partner of all five major transferable points currencies, you can transfer points/miles to Emirates at the following rates:

Although Brian has enough Amex, Chase and Citi points to book his and his fiancée’s awards, if you’re looking to replicate this itinerary and need more points, you can do so easily by adding a new travel card to your wallet. Here’s a quick overview of some of the top cards to consider (and their current welcome offers):

Related: The future of loyalty? Skywards+ lets travelers buy elite-like perks

Marriott Bonvoy hotels in the Maldives

Although Brian has a mix of Marriott Bonvoy, Hilton Honors and IHG Rewards points, we’re going to focus our attention on Marriott properties since Brian also has the three Marriott 50,000-point free night certificates.

These certificates can be used at any Category 1–6 Marriott hotel with standard award availability or Category 7 properties on off-peak nights (typically from May through June and end of August through early October). Plus, Marriott offers a fifth night free whenever you book five or more consecutive nights on points.

Related: Where to stay in the Maldives using points and miles

Marriott’s only Category 6 hotel in the Maldives is the Sheraton Maldives Full Moon Resort and Spa. However, it’s far from our favorite property here. When the TPG team visited the property a few years ago, there were a lot of flaws, such as trash in the water, disappointing overwater bungalows and a constant stream of air traffic due to the close proximity to the airport.

Sheraton Maldives
(Photo by Zach Honig/The Points Guy)

The Category 7 Westin Maldives is much nicer, serves tastier food and offers better service. The standard rooms here are beach villas and come with their own plunge pools. However, TPG’s experience there still wasn’t perfect and Brian might have trouble finding off-peak availability.

Westin Maldives
(Photo by Samantha Rosen/The Points Guy)

Their best bet would probably be to book the new Le Méridien Maldives Resort and Spa, expected to open this September. It will be a Category 5 hotel so award nights will range from just 30,000 to 40,000 points per night (or just 24,000 to 32,000 points when factoring in the fifth night free). Although they wouldn’t be “maximizing” their free night certificates if they choose to redeem them here, the remaining nights they’d book on points would be much cheaper than the other properties.

When the Le Méridien first began accepting reservations, it let you book overwater villas at the standard award rate. Unfortunately, this isn’t the case anymore, but the cost to upgrade is still very reasonable — either $100 or an extra 20,000 points per night.

Le Meridien Maldives
(Screenshot courtesy of

Brian will also need to factor in mandatory transfer costs. Although he’ll be booking the stay on points, he’ll have to pay a couple of hundreds of dollars for a seaplane or speedboat transfer from the capital of Malé (MLE) to their hotel.

Related: 10 private-island resorts you can book with points

How to book a Marriott hotel with points

The process for booking a Marriott hotel with points is just like paying cash. The only difference is that you have to check the “Use Points/Certificates” box when searching.

Book Marriott award
(Screenshot courtesy of

How to earn Marriott Bonvoy points

Brian and his fiancée will need to top off their Marriott Bonvoy balance if they want to book a week-long stay. Although they could transfer points from American Express Membership Rewards or Chase Ultimate Rewards, they’ll get more value from these points on other redemptions.

Instead, they may want to apply for one or more Marriott Bonvoy cards. In particular, the following cards offer impressive welcome offers that could help them earn enough points for this redemption. Aside from the Marriott Bonvoy Bold Credit Card, all of the cards will also provide them with additional annual free night certificates.

Of course, there are other ways to earn Marriott points as well, such as by shopping, dining and taking Uber rides.

Related: 5 ways to maximize Marriott Bonvoy award night redemptions

Bottom line

Congratulations on your upcoming wedding, Brian! Hopefully, this has helped you book the perfect honeymoon with your points and miles. And for everyone else, as you saw, their itinerary is fairly easy to replicate if you’re hoping to go on a similar trip yourself.

If you 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.

Featured photo by Samantha Rosen/The Points Guy.

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