Saving $50K in an Around-The-World Honeymoon!

Planning a world tour honeymoon started out as a perplexing points puzzle that required systems-level problem solving at a global scale! 

Highlights at a Glance 

We only had two weeks between our wedding and when Val started her full-time job as an attending physician, so I sought to plan an around-the-world trip with the following constraints: 

• Make it in time for a friend’s wedding the weekend after ours in Barcelona; 
• Avoid backtracking time zones meant continuously flying westward; and 
• Redeem fewer than a million points and miles per person. 

We set foot on 8 different time zones, spent a relaxing week across the waves of Polynesia, and enjoyed a couple of Michelin fine dining establishments in the Iberian Peninsula. According to the Air Miles Calculator, we flew more than 24,000 miles via plane (not including our hot air balloon ride) over a span of more than 50 hours up in the air. 

For folks interested in planning something similar, I’ve created a travel sheet that outlines our complete hour-by-hour itinerary, expenses, packing, and reviews.

Award Redemption 

Flights for two people (spent a total of $2,208.84 on flights worth $39,610): 

• 2 business class flights on Air Tahiti Nui from LAX to PPT retailed for $9,740. We redeemed 136,800 Qantas points transferred at a 1:1 rate from AmEx (and $243.40 in taxes and fees). 
• CPP = 100 * (9,740 - 243.40) / 136,800 = 6.94 CPP 
• 2 business class flights on Qatar Airways (QSuites) from AKL to DOH retailed for $9,900. We redeemed 280,000 Avios transferred at a 1:1 rate from AmEx (and 332.64 NZD or 206.90 USD in taxes and fees). 
• CPP = 100 * (9,900 - 206.90) / 280,000 = 3.46 CPP 
• 2 business class flights on Qatar Airways (QSuites) from DOH to BCN retailed for $5,574. For the second leg of DOH to BCN, we redeemed 86,000 Avios transferred at a 1:1 rate from AmEx (and $215.50 in taxes and fees). 
• CPP = 100 * (5,574 - 215.50) / 86,000 = 6.23 CPP 
• 2 business class flights on Virgin Atlantic (Upper Class Cabin) from MAN to JFK retailed for $14,396. We redeemed 95,000 Virgin Atlantic points transferred via 72,000 Chase Ultimate Rewards points (combined with a 2,000 referral bonus existing on my Virgin Atlantic account) during a 30% transfer bonus (and a hefty £1,211.84 or $1,543.04 USD in taxes and fees). 
• CPP = 100 * (14,396 - 1,543.04) / 72,000 = 17.85 CPP 

Reflections on further optimization: I bought the QSuite legs separately as soon as I had enough points I could transfer to Avios—I was making wedding vendor purchases during a promo period where each dollar yielded 3 additional AmEx points—I know I could have received a better point redemption if I bought these legs in one purchase, but I didn’t want to risk award availability for an aspirational honeymoon trip by waiting. I also did not know about the Virgin Atlantic 50% off companion fare until a week before the honeymoon; even though I called customer service to try to avail the offer, I was told that reversing the booking would not guarantee an Upper Class seat for my plus one. 

Accommodations for two people resulted in $13,478 of value from award redemptions: 

• 3 nights in an overwater bungalow at Conrad Hilton Bora Bora retailed for 1,191,212 XPF or ~$11,029 USD. We redeemed 360,000 Hilton Honors points from hitting sign-up bonuses on wedding vendor spend on our 2 Hilton Aspire cards. 
• CPP = 100 * (11,029 - 0) / 360,000 = 3.06 CPP 
• 1 night in Hilton Hotel Tahiti in an upgraded King Bed Premier Ocean View room retailed for $451 USD. We redeemed a free night certificate, so this stay did not cost us anything for accommodation. 
• 2 nights in AluaSoul Ibiza All Inclusive Resort in a double room retailed for $548. We redeemed for 36,000 World of Hyatt points and were not assessed taxes or fees. 
• CPP = 100 * (548 - 0) / 36,000 = 1.52 CPP 
• 2 nights in the Tapestry Collection by Hilton Atocha Hotel Madrid in an upgraded King Deluxe room retailed for $608. We redeemed 120,000 Hilton Honors points and were not assessed taxes or fees. 
• CPP = 100 * (730 - 0) / 120,000 = 0.61 CPP 
• 2 nights in The Emerald House Lisbon, Curio Collection by Hilton in an upgraded King Premium Corner room retailed for $842. We redeemed 322,000 Hilton Honors points without taxes or fees. This was the most suboptimal redemption of the whole trip, but at this point, we had over a million Hilton Honors points left and did not want to waste any more time trying to find another accommodation. 
• CPP = 100 * (842 - 0) / 322,000 = 0.26 CPP 

Travel hack for accommodations: Val and I availed the $400 resort credits for both of our Hilton Aspire cards by pre-paying for the boat transfers to and from the resort at different parts of the calendar year. We also took advantage of the card's $200 airline travel credit to book the plane fares required for island hopping. One of our wedding guests (shout out to Michael Seo!) also employed this strategy to pre-pay for our beach photoshoot activity and couples massages so that he could make the most of his Hilton Aspire credits in 2024—truly a thoughtful wedding gift for travel hackers!

Trip Report 

Activities 

• French Polynesia: Island Tour (Arahurahu Marae, Maraa Grotto, Water Gardens of Vaipahi, Faarumai Waterfalls, Arahoho Blowhole, Pointe Venus), Conrad Hilton Bora Bora Nui Resort Activities (Bike Ride to Sunset View Point, Snorkeling, Tea Time, Incense Ritual, Hilton Honors Beach, Hina Spa) 
• Auckland: Auckland War Memorial Museum, Sky Couch
• Spain: Gothic Quarter, Hi Ibiza, Hot Air Balloon Ride, Prado Museum, El Retiro Park, Michelin Dinner at DiverXO
• Portugal: Discover Lisbon Tuk Tuk Tour, Michelin Dinner at Belcanto

More to come!