TPG Reader Hall of Fame: An unforgettable $72,000 first-class honeymoon with points and miles

Editor’s note: At TPG, our top priority is providing our readers with the information needed to make educated decisions about travel and rewards-earning strategy. This is not the best time to travel, domestically or internationally, as airlines have cut major parts of their route networks. But we are sharing this information to provide value for future travel once coronavirus concerns have subsided.

If you had millions of points and miles to burn for a once-in-a-lifetime trip, where would you go?

TPG reader Daniel Reinkopf had this decision to make when he started planning an epic honeymoon with his fiancée (now wife) and realized he was sitting on a considerable cache of rewards to play with. He'd been collecting points for about 10 years, from a combination of everyday spending and using travel rewards credit cards, to booking meetings and events through his job. A year before his honeymoon, he found himself sitting on a stash of Chase Ultimate Rewards points and Marriott Bonvoy points that, combined, reached well into the seven figures.

But, he said, "I was more or less of a novice in the world of points and miles until a year or so before my wedding. [I] had very little knowledge or experience on how to maximize the amount of points I was earning, or how to use them for anything beyond a basic redemption."

Instead of just winging it, Daniel did what many travelers do when they're not sure how to use their miles — he methodically researched the best deals right here on TPG.

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Planning ahead (or 'TPG-ing') is everything

Daniel dove in and started putting together this trip piece by piece, using spare time in the evenings to fine tune his strategy.

"A year before the wedding I started consuming TPG articles every night," Daniel recalled. "My wife affectionately referred to this as 'TPG-ing.' She’d look over at me glued to the TPG app on my phone and taking notes and would ask me 'Are you TPG-ing?' I would tell her that I was taking a course on how to use points and miles to create an amazing honeymoon."

Related: From zero to hero: How to plan your luxury honeymoon with points and miles

Whenever Daniel found a post that was useful or relevant, he'd jot down the key angles for planning later. He and his wife decided they'd use their points and miles to travel further than they ever had before.

"We ultimately decided on Thailand for three main reasons: We already loved the food, the islands looked breathtaking and it’s one of the most affordable places on the planet to visit. Our wedding was set for the end of February, so if I allowed us a few extra days to recover, pack and get our affairs in order, we could arrive in Thailand by early March, which would be the start of their shoulder season, when crowds have started to die down a bit but the weather is still sunny and dry across the country."

Related: The best honeymoon destinations for every month of the year

Booking flights to Thailand

Realizing there are no direct flights between the U.S. and Thailand, Daniel set his sights on figuring out the best connection point — one that would allow a free stopover with the opportunity to explore another country. And, with a massive amount of points at his disposal, ideally on an airline that would offer a luxurious experience.

"I learned how to go about booking the flights I might want to use for our trip, as well as which airports these flights served," said Daniel. "The first decision I made was to fly Emirates for the outbound flight and take advantage of their free stopover. Neither of us had ever been to Dubai and Emirates offers one of the most luxurious first-class products in the sky."

Related: The best ways to book Emirates first class

Daniel learned he could redeem points through at least three different programs for flights on Emirates, but only one — Alaska Airlines Mileage Plan — didn't tack on massive fuel surcharges. After finding available Emirates flights on the Alaska Airlines website (and calling to confirm availability), he transferred just over a million Marriott Bonvoy points to Alaska Airlines, which converted to 360,000 Alaska Airlines miles — enough for two first-class tickets from Washington, D.C. (IAD) to Dubai (DXB) and onward to Bangkok.

Related: How to earn miles with Alaska Airlines Mileage Plan

Figuring out the return flight wasn't as simple. The couple planned on ending their honeymoon in the south of Thailand, which put them closer to Singapore than Bangkok. "This theoretically left the door open for the airline redemption I coveted most: Singapore Airlines First Class Suites featuring their 'double bed in the sky.' International honeymoon flights don’t get much more swoon-worthy!"

This redemption was more challenging because the only Singapore Airlines route with First Class Suites was Singapore (SIN) to Frankfurt (FRA) to New York-JFK. Finding saver-level award availability for two people was next to impossible, but Daniel remembered a TPG article about waitlisting for Singapore flights:

"Basically, once the requisite miles for a redemption are in your Singapore Airlines KrisFlyer account, you can waitlist as many different flights as you like. The miles aren’t deducted from your account when you waitlist a flight, so long as you have enough miles for any flight that’s available to waitlist, you can request it. Once all your waitlist requests have processed, you can then use your miles to redeem a flight that is currently available, as a backup — in case none of your waitlists ever get approved. So that’s what I did. I transferred 240,000 Chase Ultimate Rewards points into a KrisFlyer account that I set up a few days prior. At the time, that would have been enough for two saver-level first-class suites for the route we wanted. I waitlisted six different flights on the SIN-FRA-JFK route during the week that we were set to return home. Since our itinerary was pretty flexible and we didn’t have any connections that we absolutely had to make along the way, I knew I could change our plans if we got lucky enough to get approved for one of our waitlisted flights down the line. I booked us on a business-class flight from Singapore to Newark (EWR) (aka “the longest flight in the world”), as our backup."

Related: How to earn Chase Ultimate Rewards points

With flights (mostly) booked, Daniel focused his attention on maximizing his points — and elite status — for hotel stays.

Booking hotels in Dubai and Thailand

Daniel used a number of tricks from the TPG playbook to make the most of stays in Dubai and Thailand. First, he knew he could leverage his Platinum Premier (now called Titanium) Marriott elite status to status match with hotel chains. That way, he'd be able to enjoy benefits like free breakfast and room upgrades with chains other than Marriott. Status match offers come and go, but at the time Daniel made out very well — his strategy was as follows:

• Hilton: I was able to use my Marriott status to instantly upgrade to Hilton Diamond
• Wyndham: Same process to match to Wyndham Diamond
• Caesars: I used my new Wyndham Diamond status to match to Caesars Total Rewards Diamond
• MGM: I used my Caesars Total Rewards Diamond to match to MGM’s M Life Gold
• Hyatt: I used M Life Gold to match to Hyatt Explorist status

His timing for booking this trip was excellent, because in the wake of the 2018 Marriott - Starwood merger, there was a period of time where you could book top-tier Category 8 Marriott properties at Category 7 prices. An obvious pick in Dubai was Marriott's Al Maha Resort, which cost just 60,000 Marriott points per night before the new award chart kicked in (the resort now costs 100,000 points per night on peak dates).

"I had read many articles on TPG about what an amazing redemption the Al Maha Resort offered, as it was not only a gorgeous desert resort complete with individual Bedouin-style suites and private pools, but it also included three meals and two activities per day," he said. "Considering that paying for a stay at this property would have run around $4,000 per night, we were getting an amazing redemption value of 20 cents per point."

Related: Maximizing redemptions with the Marriott Bonvoy program

Daniel and his wife were tempted to stretch their stay at Al Maha to five nights, in order to take advantage of the fifth night free on Marriott award bookings. But wanting to split the stay between the desert and the city, he chose to book three nights at Al Maha and two nights in an upgraded suite at the V Hotel Dubai (which was formerly a W Hotel but now part of Hilton Honors).

In Thailand, Daniel did take advantage of the fifth night free and cheap Category 7 pricing to book five nights at the Vana Belle, a Luxury Collection Resort in Koh Samui, bringing the effective redemption rate to 48,000 points per night. "Regardless of the amazing value, the hotel looked incredible: Each room had its own private pool on a balcony with a stunning view of the Gulf of Thailand. It was centrally located, had a beautiful private beach and a phenomenal-looking breakfast buffet which was offered complimentary to Marriott Platinum Elites and higher."

For their time in Bangkok, Daniel booked three nights (25,000 points per night) at Le Meridien Bangkok, which is known for its amazing breakfasts. In Chiang Mai, he booked three nights (30,000 Hyatt points per night) at the 137 Pillars House, a property that had recently been added to World of Hyatt through their Small Luxury Hotels of the World (SLH) partnership. As a newly-matched Hyatt Explorist, this stay came with complimentary breakfast.

Both Daniel and his wife are SCUBA certified, so they wanted to spend time diving around the smaller islands where there aren't any chain hotels. "We had read that Koh Tao offered some of the best diving in the world," Daniel recalled. "Plus, if we timed it correctly, we could visit Koh Phangan for the night of their legendary Full Moon Party. After doing a bit of research (including contacting TPG's Lori Zaino for some first-hand expertise – thank you Lori!), I booked a breathtakingly beautiful resort on Koh Tao called View Point Resort. Similarly, I booked another gorgeous resort on Koh Phangan called Kupu Kupu by L’Occitane."

To maximize these bookings, Daniel took advantage of a promotion (no longer available) with the Capital One Venture Rewards Credit Card and hotels.com. At the time, you could earn an elevated rate of Capital One Venture miles on hotels.com bookings. "$750 at Kupu Kupu became 7,500 Capital One miles. I also received nightly credits towards a free night on a future Hotels.com booking. Not too shabby!"

One last, clever tip: For all hotel reservations, Daniel put a note in the comments section of the booking that he and his wife were on their honeymoon.

Related: The best hotel credit cards

A points-and-miles honeymoon to remember

Here's how it turned out for the newlyweds.

Emirates first class

On the way to Dubai, Daniel and his wife sat next to each other in middle seats, then from Dubai to Bangkok they tried out the windows. And yes, they got to experience the legendary A380 Emirates First Class shower in the sky and onboard bar and lounge. If booked with cash, these Emirates First Class tickets would have cost $12,049 per person ($24,098 total).

They enjoyed Dom Perignon and caviar on both legs, but the red-carpet treatment didn't stop there. "Emirates also offers a chauffeur experience from DXB to your hotel if you’re traveling on First or Business. I had read that this benefit was not available to prebook if your tickets were from a partner redemption as ours were. But I had also read that other travelers had success when presenting their tickets to the limousine transfer desk in person, so we gave it a shot," said Daniel.

"Sure enough, our first-class tickets were all that was needed and we were whisked away to Al Maha in a complimentary limousine. Considering this desert resort is located 30 miles from the airport, this was a great perk to an already phenomenal flight. The lesson: it never hurts to ask or try!"

Dubai

Daniel can't say enough about their stop in Dubai. "Our experience at Al Maha was sublime. The desert resort was the perfect place for us to recover from our jetlag and take it easy for a few days. We were treated to three phenomenal meals and two desert activities each day. We opted for an introduction to falconry, a desert jeep tour, an evening camel ride and an archery lesson — all of which were included free of charge as part of the redemption at this property." The accommodations were impressive, too. "Our room ­— like every room at this resort ­— was a Bedouin-style tent, complete with a private pool where gazelles would come to greet us every morning. It was 'glamping' at its best and a really fun way to start our honeymoon." If paid with cash, this three-night stay would have clocked in at $12,103.

Their time spent in the city was incredible. In just a few days, they hit the major highlights, including visiting the top of the Burj Khalifa — the tallest building in the world — and having drinks on the promenade of the luxurious Burj Al Arab hotel (one of the world's only seven-star hotels).

Daniel also remarked that the V Hotel Dubai is one of the most modern properties he and his wife have ever stayed at. "Our room looked like something out of Star Trek!" Their two-night stay in a suite would have cost nearly $1,200 but instead they redeemed 222,000 Hilton points.

Related: Maximizing redemptions with the Hilton Honors program

Thailand

Daniel and his wife were blown away by their time in Thailand, in particular the rock-star treatment they received at their hotels. "The reviews of the Le Meridian Bangkok proved to be spot-on. The breakfast buffet offering was probably the most elaborate of our entire trip, and the hotel upgraded us to their best 'round bed suite,' with little rose petals arranged on the bed along with a very nice welcome note. The lesson: It definitely pays off to let a hotel know of a special occasion in advance."

Another outstanding experience was had at the Vana Belle, where they were upgraded to the Grand Ocean View Pool Suite, with incredible views of the Gulf of Thailand and a complimentary breakfast buffet. "Probably the second best breakfast of the trip, after Le Meridien's."

Related: The 11 hotel breakfasts we'd order for every meal if we could

Singapore Airlines first class

So what happened with the Singapore Airlines waitlist strategy? Daniel had read reports on TPG from folks who had success calling the airline about their waitlist status, so once or twice a week he'd give them a ring. "Each time I spoke to an agent, I politely mentioned that it was our honeymoon and how grateful and thrilled we would be to have the Singapore Suites experience. Five days before our backup flight home was set to depart, I received the email: Our waitlist for the JFK-FRA-SIN flight was approved."

But there was one last issue:

"All of the coveted middle seats (which converted to their double beds) were already taken. This was somewhat of a bummer, but I figured there was always the (admittedly slim) chance that someone on either the SIN-FRA or FRA-JFK flight might be willing to swap seats with us. So we booked two window seats, I canceled my backup flight, and hoped for the best. On the day of our departure, we checked into our flight at Changi Airport. I asked the agent at the ticketing counter to please see if there may be a chance to score two middle seats for either flight, again mentioning that it was our honeymoon. I held my breath while she spoke with two of her colleagues. Three minutes later she came back with great news: While there was no availability in center seats on the way to Frankfurt, they could seat us together on the FRA to JFK flight. We were thrilled and proceeded to thank them profusely. This worked out perfectly as the flight to FRA departed at midnight, so we slept (in our separate window suites) for the entire first half of the trip."

In Frankfurt, the couple disembarked for just over an hour and enjoyed breakfast at the Star Alliance lounge before boarding for the final leg of their journey. Daniel and his wife made the most of it, sipping champagne and watching movies in their lie-flat double bed. And then came a surprise: The agents at the airport must have let the crew know about their honeymoon, because two flight attendants presented the couple with a beautiful cake, teddy bears and a signed card congratulating them. "It was the perfect end to an amazing honeymoon," Daniel said.

He added, "The cash value of two first-class tickets on this flight was about $17,000. While that’s not quite as expensive as the cash equivalent for the Emirates flights, it’s again WAY more than we’d ever have spent on a flight, and ultimately, an experience that we would not have had if it weren’t for the knowledge I picked up on TPG."

Bottom line

All told, Daniel and his wife traveled for a full month, and spent only $6,300 out of pocket including airline taxes, domestic flights, paid hotel stays, meals, ferries, taxis, souvenirs and entertainment. Had they spent cash for the whole trip, their travel bill would have been over $72,000.

What were Daniel's key takeways?

• The more difficult the redemption, the more it pays to keep on trying to the very end (in our case right up until the day of our flight!)
• Often times, the really premium seats only become available two weeks out. Having a backup flight and the flexibility to change it can really open up some exciting options!
• By reading about the myriad ways to use points and miles, we had a honeymoon neither of us will never forget, and got to experience some of the most aspirational flights in air travel.

Daniel, your attention to detail leaves us in awe. We're thrilled you were able to find the tools you needed on TPG to plan this incredible trip. Well done and congratulations!

Have an epic points and miles adventure to share? Email your story to info@thepointsguy.com (put “TPG Reader Hall of Fame” in the subject line), message us on Facebook, or tell us about it in the TPG Lounge; be sure to include details about how you earned and redeemed your rewards. Due to the volume of submissions, we can’t respond to each story individually, but we’ll be in touch if yours is selected.

All photos courtesy of Daniel Reinkopf.