How I saved over $40K booking a bucket list trip for two

One of the optimal strategies in the travel hacking hobby is to “churn and burn.” Hoarding points over extended periods of time is risky, because like fiat currency, points and miles devalue over time. We know from basic economics that a dollar today is always stronger than a dollar tomorrow due to inflation. 

Using points and miles for aspirational travel 

Booking for more than one person (e.g., couples trips with a player two or family trips with children) adds complexity around availability (finding seats that are next to each other and accommodations that constrain bookings to 2 adults per room). With more than 2 million points and miles among me and my partner over the span of 2 years, we were long overdue for a post-lockdown revenge splurge. I did 100% of the planning for this engagement trip (I kept most of our activities a surprise from her until the day we took off from the states) and ended up only needing a fraction of my stash of points that were accrued primarily from credit card welcome bonuses and everyday spend multipliers. This meant that I can easily repeat this seemingly once-in-a-lifetime excursion again (hello, honeymoon).

The math gets complex, so please let me know in the comments section if you have any questions!

Breaking down the calculus of award redemption step-by-step

While the travel hacking blogerrati assigns different values to each loyalty program, when it comes to burning points and miles, I consider any award redemption above 2 CPP as outsized in redemption value. Redemption value is the cent-per-point (CPP) that excludes any added expense incurred as a result of booking an award. The formula I use to calculate CPP is as follows: CPP = 100 * (Cash Prize - Expenses) / (Award Prize).

Flights for two people (337,500 total AmEx MR points transferred 1:1 to Emirates Skywards; 290,000 total Delta Sky Miles redeemed for Air France flight):

• First class suites on Emirates from IAD to DXB retailed for $26,796.
• Redeemed via 272,500 Skyward miles (and $361.20 in taxes and fees)
• CPP = 100 * (26,796 - 361.2) / 272,500 = 9.70 CPP
• Business class on Emirates from DXB to MLE retailed for $3,889.
• Redeemed via 105,000 Skyward miles (and $157.92 in converted taxes and fees)
• CPP = 100 * (3,889 - 157.92) / 105,000 = 3.55 CPP
• Business class on Air France from MLE to JFK retailed for $7,937.
• Redeemed via 290,000 Delta Sky Miles (and $398.30 in converted taxes and fees)
• CPP = 100 * (7,937 - 398.30) / 290,000 = 2.60 CPP

Hotel for two people (185,000 total Chase UR points transferred 1:1 to World of Hyatt):

• 1 night in upgraded suite in Hyatt Regency Dulles retailed for $107.
• Redeemed via 5,000 World of Hyatt points (and $0 in taxes and fees)
• CPP = 100 * (107 - 0) / 5,000 = 2.14 CPP
• 5 nights in upgraded beach pool villa at Park Hyatt Maldives retailed for $7,079.
• Redeemed via 150,000 World of Hyatt points (plus $1,099.99 in seaplane transfers for two and $739.20 for a room supplement to upgrade our last 2 nights to an overwater sunset pool villa)
• CPP = 100 * (7,079 - (1,099.99 + 739.2)) / 150,000 = 3.49 CPP 
• 1 night in upgraded suite in Park Hyatt Paris retailed for ~$827 USD (€792).
• Redeemed via 30,000 World of Hyatt points (and $0 in taxes and fees)
• CPP = 100 * (827 - 0) / 30,000 = 2.76 CPP

Without redeeming airline miles, the retail value of both of our premium cabin flights roundtrip would have totaled ~$38,622. On the same vein, without redeeming hotel points, the retail value of our scenic stays would have totaled ~$8,013 USD. Using a combination of hotel points and airline miles, I just needed to pay $917.42 out of pocket for this entire trip to cover the required excise taxes and fees of two butts-in-seats, $1,099.99 for the resort transfer for two bodies via seaplane, and an optional $739.20 for a bungalow upgrade with a private pool. In other words, approximately 94.09% (or $46,635) of the trip has been subsidized by award redemptions with me only having to pay 5.91% (or $2,756.61) of what the trip was actually worth (which were also eligible to be reimbursed further with particular credit cards that cover airline incidentals). For the sake of simplicity, I only included travel-related redemptions in the analysis (so items like the engagement ring or souvenirs or rideshares to and from the airport were out of scope for this report).

Mentally accounting for an around-the-world adventure

The resort accommodation was significantly easier to budget for since World of Hyatt (currently) sticks to a predictable redemption chart. Even though Globalist room upgrades do not apply on select resort properties like the one in Hadahaa, I was comfortable splurging a bit to secure an overwater pool bungalow because the trip served a special occasion. I raked in over 2 CPP for each stay on this vacation, which is an all-around win across three continents!

In optimizing for optionality in seat selection, I was more interested in trying out a variety of different cabins than restricting our travels to hard-to-find first class redemptions. After extensive sleuthing, I found first-class suite availability on Emirates (a travel hacker’s dream redemption), but needed to depart from IAD to do so (yes, there were no other available departures from American hubs like JFK, BOS, DFW, IAH, ORD, LAX, SFO, SEA on the weekend we slotted PTO for travel). While the Air France itinerary I found didn’t have the La Première first-class equivalent (which became even more elusive in the pandemic), business class remained an excellent option for catching up on sleep via lay-flat seating, and I redeemed this award using the less valuable Delta Sky Miles I had in stockpile instead of my more valuable American Express Membership Rewards points. Both Emirates and Delta have dynamic pricing to take into consideration, which fluctuates with the supply and demand of award travel, which is even harder to account in a pandemic. 

Overall, I felt satisfied with redeeming 852,500 points and miles that covered the bulk of transportation and accommodation for two adults in premium class and comfort. I’m sure savvier travel hackers could find even better deals than I could, but given the sheer number of unexpected twists and turns that went into preparing for this trip, I’ll take what I can get so that I can shift my attention from planning mode to living large.