$32,000 Success Story: Dream Trip to a Private Maldives Resort Island

Chances are, you’ve seen beautiful pictures of the Maldives on Instagram showcasing the gorgeous waters and sandy beaches and, of course, the over-water villas. And maybe you’ve stuck the possibility in your mind as a “someday” trip. These images have turned this small island nation into a bucket-list trip for many.

This destination caught the eye of Travel Freely team member Cheryl, who through a combination of points and miles strategy and hotel status, was able to book a 2-week trip on a private island in the Maldives for her and her husband Carter, saving them $32,000 in the process!

How Cheryl used points to book a Maldives dream vacation

There are a variety of ways that you can visit the Maldives on points. Given the type of points Cheryl had accumulated (Chase Ultimate Rewards points and American Airlines AAdvantage® miles) and the redemption possibilities available, she booked Qatar Airlines Q-Suites lay-flat business class seats and a 14-night stay at the Park Hyatt Maldives Hadahaa, all on points. With lay-flat seats, the Qatar Business Class Lounge access, and a private island, she knew this was going to be an epic trip.

Note: Point redemptions and credit card offers may have changed since the publishing of this post.

Booking the Hotel

Park Hyatt Maldives Hadahaa

The Park Hyatt Maldives Hadahaa is a well-established top-tier destination resort. This Hyatt Category 7 private island resort has everything you need for a fun, relaxing, disconnect-from-the-world vacation. Cheryl says the resort lives up to the hype.

The resort only releases rewards stay availability for their lowest level villa, which is a Standard Beach Villa. Fortunately, all of the villas at the Park Hyatt are beachfront villas (the beauty of being a small island!). Each villa has a very short path to the beach and includes your own umbrella and lounge chairs. Quiet sunrises and sunsets, beautiful beaches, and some of the world’s best SCUBA diving and water sports lets you be as active or as lazy as you want to be. (Note – hotels and resorts in the Maldives are required to include a 10% service charge and a 16% Goods and Services Tax (GST) for all purchases.)

A fan of the Hyatt brand, Cheryl is also a Hyatt Globalist. Because of her status, Cheryl got a 1-category room upgrade from a Beach Villa (the only one bookable on points as mentioned above) to a Beach Pool Villa with their own small pool. She and Carter also received free breakfast each morning and drinks and appetizer plates every afternoon. Additionally, Hyatt left them a bottle of Prosecco and a tray of fruit, cheese, and nuts upon arrival.

How Cheryl Accumulated the Hyatt Points

One of the very cool features of having Globalist status, like Cheryl, is that you can make an advance booking BEFORE you actually have the points in your account. Cheryl wanted to do 14 nights at the Park Hyatt Hadahaa, which came in at 375,000 points total, an average of 26,785 points per night. This meant she was able to make the booking 11 months in advance and the entire amount of points didn’t have to be in her account until 2 weeks prior to the start of her stay.

That felt like a huge number, but she was confident she could make it work. She had about 50,000 Chase points in her account from regular spending and a few points left over from a card signup bonus that she hadn’t yet used – woohoo! – so she had 325,000 points to go! She’s also lucky enough to have a very willing P2 in her husband who could help to earn the points needed. (Check out this article that talks about strategy with your significant other!)

First, Cheryl’s husband Carter opened a Chase Sapphire Preferred® Credit Card and transferred the points to Hyatt. He then made a request to combine points (essentially transferring them) from his Hyatt account into Cheryl’s. Keep in mind, you can only do a combination request once per month, and it does take about a week to process.

• Cheryl then opened a Chase World of Hyatt Business Credit Card. That card also gives her 9X on Hyatt spend.
• She then opened an Chase Ink Business Preferred® Credit Card.
• Finally, Carter opened an Chase Ink Business Cash® Credit Card.

That took them up to 330,000 points, and along with 50,000 points Cheryl already had in her Hyatt account, they had the 375,000 points needed for the Park Hyatt stay.

Once the last bonus had posted and the points were transferred to Hyatt, Cheryl contacted her Hyatt Concierge (another Globalist benefit) and asked her to go ahead and process the award. This meant that there was no chance of Cheryl not having the total points needed 2 weeks prior to the trip which would result in her being charged the full cash rate (non-refundable or cancelable!) because she accidentally used the points on other stays they had before the Maldives trip.

Booking the Flights

Cheryl figured if they were doing an epic trip to the Maldives, the flights had to be equally as epic. So they set their sights on Qatar Airlines Q-Suites, which has a reputation for having one of the best business class experiences. One of the things to remember about coveted award flights like Q-Suites is that you have to look for them as soon as the calendar opens availability, which is usually a year in advance.

Because American Airlines (AA) is a partner of Qatar Airways, Cheryl looked at booking flights with AA. Booking flights on airline partners is a great way to either get flights using fewer points and/or taxes and fees or to use points you have already have available. Sometimes the best flight is the one you have the points to take!

Note: These points were accumulated from signup bonuses achieved through the AAdvantage® Aviator® Red World Elite Mastercard® and the Barclays AAdvantage Aviator Business Mastercard. The AA Business Card is not currently available for new applications.

Round-trip Flights from Chicago to Male, Maldives

Often when Cheryl is booking flights, there is a hurdle based on where they live. The closest airport is in Kansas City, MO, a flyover state, which means it has a small airport with limited options, and it’s highly unlikely they’ll find any great deals on points out of Missouri. So Cheryl usually looks for award flights starting from a major hub like Chicago or Houston and then takes what’s called a positioning flight much earlier in the day (or the night before and stays in a hotel using points) to then catch the main flight.

Through some dedicated research, Cheryl secured award seats at 70,000 points per person each way for a total of 280,000 points for round-trip airfare from Chicago to Male for 2 people. These aren’t cheap flights – you can definitely find cheaper ways to get to the Maldives. But, Cheryl and Carter wanted to go big and fly in real luxury. The taxes and fees for their award flights there and back cost a total of $430.14 for 2 people. A steal considering how far they were flying round-trip in the coveted Q-Suites!

The original booking through American Airlines for flights on Qatar took Cheryl and Carter from Chicago to JFK, then JFK to Doha, Qatar, and Doha to Male. The return flights were Male to Doha and then straight to Chicago. The JFK to Doha and Doha to Chicago flights were business class flights on Qatar in the fabled Q-Suites, while the flights between Doha and Male were essentially the same seats, but didn’t have the Q-Suite compartment walls. The flight from Chicago to JFK was in first class on American Airlines. What a treat!

Keep in mind that you usually have to pay for private transport from Male to your hotel, which in Cheryl’s case was $550 per person round-trip. There’s no way around this, but one way to cover this travel expense is to open a Capital One Venture Rewards Credit Card or Capital One Venture X Rewards Credit Card, charge it to the card, and use your Capital One Miles to reimburse the travel expense.

Travel Freely Pro Tip: If you need help knowing your best points and miles options, consider using a free award search tool like PointsYeah.

Note: Besides using AA miles to book, you can transfer American Express Membership Rewards and Marriott Bonvoy™ Points directly to Qatar. Marriott is not recommended due to the 3:1 transfer ratio. In addition, Chase Ultimate Rewards, Citi ThankYou® Points, and Capital One Venture Miles can be transferred to British Airways and then moved to Qatar once your accounts are linked. Check out our Loyalty Programs and Transfer Partners article for help figuring out which points transfer where and who parters with whom.

Time on the Island

Cheryl says the moment they arrived in the Maldives, it was like stepping straight into a postcard. Each day started with a sunrise that painted the sky in incredible colors and ended with sunsets that were even more spectacular. They’d wander from their villa to the beach, just a few sandy steps away, or gently paddle around in a kayak, the water around them as clear as glass.

For a closer look beneath the surface of the crystal waters, Cheryl and Carter strapped on SCUBA gear or grabbed snorkels to check out the vibrant reefs teeming with fish. It was like swimming in a giant aquarium! When they weren’t underwater, they spent plenty of lazy hours in their beach villa, soaking in the endless ocean views and the calming sounds of the water.

The Culinary Experience

Eating was another kind of adventure. The Park Hyatt Maldives Hadahaa offers a menu as varied as the ocean life, with a focus on the freshest seafood you can imagine. Cheryl loved the themed dinner nights where they could taste everything from local Maldivian dishes to international favorites, each one as delicious as the last.

Concluding Thoughts

When Cheryl looks back, she says what truly stood out about the Maldives was the perfect mix of thrill and tranquility. It’s a slice of paradise that she could afford thanks to smartly using her stashes of points and miles. For anyone dreaming of their next big trip, the Maldives is a solid bet — it turns daydreams into reality, rewarding every point spent with unforgettable moments.

No matter if it’s your first big trip or you’re a seasoned points collector, the Maldives offers an escape that’s out-of-this-world. Every redeemed point here feels like a worthwhile investment into peace, beauty, and awe.

Final note – Cheryl also says the thought of going back to the Maldives is tempting — it’s hard to say no to a place that’s left such a strong, lasting impression. If you’ve been thinking about the Maldives, take this as your sign to start planning. Let Travel Freely help you earn and use those points and miles for a journey that’ll stick with you forever!

Cards mentioned in this post: