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Cleared for Takeoff: Using points and miles for an epic 20th anniversary on a private island

The Points Guy logo The Points Guy 9/14/2021 Benji Stawski
a body of water © Provided by The Points Guy
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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.

Any anniversary is cause for celebration, but certain milestones deserve a little more thought. So, for today’s Cleared for Takeoff story, we’re going to help TPG reader Richard Manning book an unforgettable 20th anniversary trip.

More specifically, we’re going to help him book a getaway to a private island in the Seychelles. Richard was concerned that a destination like the Seychelles might not have enough activities for him and his wife, but as you’ll see later, they won’t run out of things to do at the resort.

I’ve been enjoying your columns for a while now and they have always been incredibly informative — thank you!

My 20th wedding anniversary is coming up next year (October 2022) and I would like to take a week-long romantic trip somewhere (provided things will have opened up for Americans to travel abroad in this post-COVID world – both my wife and I have been fully vaccinated). A beach vacation to Bora Bora or the Maldives or even the Seychelles seems like a quintessential trip in theory (and certainly an iconic 20th anniversary destination) but may be too boring if it’s a full week of just lounging around a beach as we’re both pretty active — we enjoy hiking and sightseeing in addition to lounging on a beach/pool or spa.

Do you have any suggestions of places we could go?

Richard has a hefty stash of American Express Membership Rewards points, Marriott Bonvoy points, American Airlines AAdvantage miles and Delta SkyMiles. Follow along as I share how they should redeem their points and miles for this epic trip.

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In This Post

Current points stash

a tree next to a body of water: (Photo by Laurence Monneret/Getty Images) © The Points Guy (Photo by Laurence Monneret/Getty Images)

Richard currently has over a million American Express Membership Rewards and Marriott Bonvoy points, as well as plenty of American Airlines and Delta miles. He should have no trouble covering both airfare and hotels with his current balance.

Richard mentioned that he was able to earn such a large balance by stockpiling his points following the switchover from Starwood Preferred Guest to Marriott Bonvoy. He also earns points with cards like the Chase Sapphire Reserve, American Express® Business Gold Card, Marriott Bonvoy Amex and Marriott Bonvoy Business™ American Express® Card.

Related: A guide to earning transferable points and why they’re so valuable

Round-trip airfare to the Seychelles

a close up of an office chair: (Photo by Benji Stawski/The Points Guy) © The Points Guy (Photo by Benji Stawski/The Points Guy)

Route: RDU-PHL-DOH-SEZ on Qatar Airways in business class; SEZ-DOH-PHL-RDU on Qatar Airways in business class.

Miles needed: 75,000 American Airlines miles plus $30.70 per person on the outbound flight; 75,000 miles plus $86.65 on the return.

The closest airport to Richard and his wife is Raleigh-Durham (RDU) in North Carolina. There are no nonstop or even one-stop flights to Mahe, Seychelles, from there so they’re going to want to fly comfortably for the multistop journey.

One of the best ways to travel between the U.S. and Africa is Qatar Airways business class. Not only is it reasonably priced when booking with American Airlines miles, but it’s also one of the poshest business-class products in the skies.

Plus, most Qatar flights between the U.S. and Doha, Qatar, feature Qatar’s Qsuite, which offers couple-friendly seats in the middle of the plane that can be converted into a double bed for two.

As mentioned, Richard and his wife will need to have at least two layovers — one in one of Qatar’s U.S. gateway cities, such as Philadelphia (PHL), and another in Doha (DOH). While American doesn’t offer free stopovers, the couple may be able to explore Doha by booking an extra-long layover there. After all, Richard did mention that he’d like to do some sightseeing on this trip.

Related: Maximizing redemptions with American Airlines AAdvantage

a large body of water with a city in the background: (Photo by Matteo Colombo/Getty Images) © The Points Guy (Photo by Matteo Colombo/Getty Images)

How to book this award with points

Richard and his wife’s anniversary is in October 2022. However, you can only book Qatar Airways awards through American Airlines 331 days or less before departure so they won’t be able to book their award flights yet.

Gallery: The Top 10 Best Travel Hacks To Save the Most Money (GOBankingRates)

Once it’s time for them to book their flights, they’ll be able to do so fairly easily directly through American’s website. On the airline’s homepage, enter your route (in this case, RDU-SEZ), select your dates and check off the “Redeem miles” box.

graphical user interface, text, application: (Screenshot courtesy of © The Points Guy (Screenshot courtesy of

On the next page, you’ll be shown 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. Alternatively, in Richard’s case, it might make sense to search out of a gateway city like Philadelphia (PHL) or New York-JFK outright and book a separate positioning flight.

Since Richard and his wife will have multiple stops, it’s extra important for them to make sure they’re not booking a mixed cabin itinerary.

graphical user interface, application: (Screenshot courtesy of © The Points Guy (Screenshot courtesy of

The final step is to log in to your AAdvantage account to complete the booking. The round-trip business-class ticket costs 150,000 miles per person regardless of where in the U.S. you’re departing from, and the taxes and fees on this ticket should come out to around $120.

How to earn enough miles for this award

Richard already has about 280,000 American Airlines miles, but he’ll need 300,000 miles to book the two round-trip awards.

The options for transferring miles to AAdvantage are fairly limited, but not nonexistent.

For instance, Marriott Bonvoy points transfer to American at a 3:1 ratio, and you’ll get a 5,000-mile bonus for every 60,000 points you transfer.

If Richard had any Citi ThankYou-earning cards, such as the Citi Premier® Card, he’d also be able to transfer ThankYou points to AAdvantage through Nov. 13. Those with a Citi Prestige® Card, Citi Premier Card or Citi Chairman Card can transfer points at a 1:1 ratio. Citi ThankYou Preferred (no longer available for new applicants) and Citi Rewards+® Card cardholders can transfer points at a 2:1 ratio.

There are also opportunities to earn American Airlines miles with other partners. For example, American Airlines elite members can earn American Airlines miles on World of Hyatt stays. You can also earn miles by shopping online through the AAdvantage shopping portal or by dining with AAdvantage dining rewards.

But perhaps the easiest option is to pick up a cobranded American Airlines credit card. Here are some cards to consider and their current sign-up bonuses:

  • AAdvantage Aviator Business Mastercard: Up to 80,000 miles: 50,000 miles after spending $1,000 in the first 90 days of account opening, plus 30,000 miles after spending a total of $6,000 within the first 12 months.
  • CitiBusiness® / AAdvantage® Platinum Select® Mastercard®: 65,000 miles after you spend $4,000 on purchases within the first four months of account opening.
  • AAdvantage Aviator Red World Elite Mastercard: 60,000 miles after making a purchase and paying the annual fee within the first 90 days of card opening.
  • Citi® / AAdvantage® Platinum Select® World Elite Mastercard®: 50,000 miles after you spend $2,500 on purchases within the first three months of account opening.
  • Citi® / AAdvantage® Executive World Elite Mastercard®: 50,000 miles after you spend $5,000 on purchases in the first three months of account opening.

The information for the Citi Chairman card, 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.

Hotel in the Seychelles

Marriott Bonvoy has just one property in the Seychelles and it’s truly one of a kind. Enter North Island, a Luxury Collection Resort.

a pool next to a tree: North Island, Seychelles. (Photo courtesy of North Island, a Luxury Collection Resort) © The Points Guy North Island, Seychelles. (Photo courtesy of North Island, a Luxury Collection Resort)

This resort is set on a private island and has just 11 rooms. The entry-level room is a nearly 5,000-square-foot two-bedroom villa with a private pool. Although this might seem like the type of vacation where you lounge on a beach all day, the resort offers plenty of activities to keep Richard and his wife entertained. These range from scuba diving to kayaking to stand-up paddleboarding to cycling to yoga classes to guided walks and more. Every stay also includes complimentary breakfast and use of an island buggy.

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

As you’d expect, stays here don’t come cheap. Awards cost 388,000 Marriott points per night, though that price goes down a bit when booking five or more consecutive award nights thanks to Marriott’s fifth-night-free perk. Richard currently only has enough Marriott Bonvoy points for three nights but can boost his balance by transferring points from American Express Membership Rewards. Plus, Amex is offering a 30% bonus on all transfers to Marriott Bonvoy through Oct. 31. This means that each additional award night costs 299,000 Amex points, before factoring in the free-fifth-night discount.

Although that’s a lot of points, Richard will be getting some serious value from his points. Cash rates are often around $7,000 per night. He’ll just need to look out for extra fees, such as the mandatory helicopter transfer that costs 814 euros each way (around $960.25).

a room filled with furniture and a large window: North Island Resort. (Photo courtesy of North Island, a Luxury Collection Resort) © The Points Guy North Island Resort. (Photo courtesy of North Island, a Luxury Collection Resort)

How to book a Marriott hotel with points

The process for booking this hotel is just like paying cash. The only difference is that you have to check the “Use Points/Certificates” box when searching. Note that this hotel has a four-night minimum stay requirement.

graphical user interface, text, application, email: (Screenshot courtesy of © The Points Guy (Screenshot courtesy of

Related: How to spend a million Marriott points for an epic post-pandemic trip

How to earn Marriott Bonvoy points

Richard will need to supplement his Marriott Bonvoy balance to cover the entire stay with points. 

As mentioned, one option would be to transfer from American Express Membership Rewards. Although we normally don’t recommend transferring Amex points to Marriott, as you’ll generally lose value, it could make sense in this scenario if Richard is able to take advantage of the 30% bonus currently available

Another option would be to pick up more Marriott Bonvoy cards, especially if Richard’s wife doesn’t have any yet. Here are the bonuses currently available on Marriott Bonvoy cards. Aside from the Marriott Bonvoy Bold Credit Card, all of the cards will also provide them with annual free night certificates.

  • Marriott Bonvoy Brilliant™ American Express® Card: Earn 75,000 Marriott Bonvoy bonus points after using your new card to make $3,000 in purchases within the first three months of card membership. Plus, earn up to $200 in statement credits for eligible purchases made on your new card at U.S. restaurants within the first six months of card membership.
  • Marriott Bonvoy Boundless Credit Card: Earn three free night awards (each free night award has a redemption value of up to 50,000 bonus points, for a value of up to 150,000 total points) after you spend $3,000 on purchases in the first three months from account opening. Plus, earn 10x total points on up to $2,500 in combined purchases at grocery stores, restaurants and gas stations within the first six months from account opening.
  • Marriott Bonvoy Business™ American Express® Card: Earn 75,000 Marriott Bonvoy bonus points after you use your new card to make $3,000 in purchases within the first three months. Plus, earn up to $150 back in statement credits on eligible purchases made on your new card within the first three months of card membership.
  • Marriott Bonvoy Bold Credit Card: Earn 30,000 bonus points after you spend $1,000 on purchases in the first three months from account opening.

Related: 5 ways to maximize Marriott Bonvoy award night redemptions

Bottom line

Congratulations on the upcoming anniversary, Richard! It’s great that you’re planning this trip so far in advance since it’ll give you extra time to earn the remaining points you need and allow you to jump on award flights as soon as they become available.

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 courtesy of Marriott.

SPONSORED: With states reopening, enjoying a meal from a restaurant no longer just means curbside pickup.

And when you do spend on dining, you should use a credit card that will maximize your rewards and potentially even score special discounts. Thanks to temporary card bonuses and changes due to coronavirus, you may even be able to score a meal at your favorite restaurant for free. 

These are the best credit cards for dining out, taking out, and ordering in to maximize every meal purchase.


Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.


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