How We Booked a $20,000 Vacation With Points

#289: Chris and Amy booked a last-minute week in Bora Bora that would have cost over $20,000, almost entirely on points. They break down how it came together, why they chose Bora Bora over Fiji, the Marriott award search quirk that hid available rooms, flying business class in both directions by mixing two airlines, and using card travel credits on the inter-island flights. Then, three nights in, they decided to abandon the deal and pay more to switch resorts. They compare and rank the major Bora Bora resorts, weigh points versus cash, and explain what makes French Polynesia one of the easiest long-haul trips from the West Coast.

Link to Full Show Notes: https://chrishutchins.com/bora-bora-on-points-2026/

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Resources Mentioned

Hotels & Resorts

• Hotel Upgrade Program
• The Westin Bora Bora Resort & Spa
• Four Seasons Resort Bora Bora
• The St. Regis Bora Bora Resort
• Conrad Bora Bora Nui
• The Brando
• Le Taha'a
• Nanuku Resort
• Waldorf Astoria Costa Rica
  
  

Products

• Monopoly Deal
  
  

Health & Sauna Research

• Bryan Johnson — Is Sauna ACTUALLY Good For You? (90-Day Experiment)
  
  

ATH Podcast

• #285: Why Net Fulfillment Beats Net Worth with Bill Perkins
• #287: Putting Die With Zero Into Practice with Brad Barrett
• Hotel Upgrade Program
• Best Cards Page
• Gift Cards Page
• Newsletter
• AMA: Submit Questions
• Leave a review: Apple Podcasts | Spotify
• Email for questions, hacks, deals, and feedback: [email protected]
  
  

Full Show Notes

(00:00) Introduction
(02:09) How a Kid-Free Trip Came Together
(03:33) How Chris and Amy Choose Vacation Destinations
(13:09) Why French Polynesia Over Fiji
(14:59) Booking The Westin
(20:43) Flying Business Class Both Ways on Two Different Airlines
(26:22) Air Tahiti Nui and the Inter-Island Flights
(31:15) A Surprise First Class Upgrade on Air Moana
(32:47) Arriving in Bora Bora and Checking Into The Westin
(34:29) First Impressions: A Brand-New Property with Great Bones
(37:33) A Thousand Little Cuts: The Westin's Service Problems
(44:50) The Math Behind Checking Out Early
(52:21) The Four Seasons vs. The Westin: What the Extra Money Buys
(59:23) Why the Four Seasons Spa Facilities Stood Out
(01:00:37) Getting Serious About Sauna Again
(01:05:51) Pickleball, Paddleboarding, and Space to Get Lost
(01:08:00) Did the Four Seasons Save the Trip?
(01:13:18) How to Actually Get Deals at the Four Seasons
(01:16:20) Ranking All Four Bora Bora Resorts
(01:19:32) Why Fiji Is Still at the Top of the List
(01:21:45) Where AI Can Go Wrong
(01:23:15) Packing a Travel Med Bag for Remote Destinations
(01:24:20) Final Thoughts and Why Bora Bora Keeps Winning

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