TPG Reader Hall of Fame: The ultimate luxury vacation

Oct 25, 2019

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Today’s TPG Reader Hall of Fame story comes to you courtesy of Tom, who took the ultimate bucket-list vacation with his wife — an ultra-luxury 11 days spent on board some of the finest cabins and in the fanciest hotels around the world. Let’s see how they did it.

Photo courtesy of Tom Ainsworth.
(Photo courtesy of Tom Ainsworth)

Tom and his wife splashed out for a high-end vacation at one of our favorite properties — the Conrad Maldives — combined with some truly incredible nights at the Conrad Singapore and the JW Marriott Dubai.

Photo courtesy of Tom Ainsworth.
(Photo courtesy of Tom Ainsworth)

To swing this they applied for a number of credit cards, including:

  • Alaska Airlines Visa Signature® credit card — Limited Time Offer: Earn a $100 statement credit, 40,000 bonus miles and Alaska’s Famous Companion Fare™ from $121 ($99 fare plus taxes and fees from $22) after you make $2,000 or more in purchases within the first 90 days of opening your account.
  • Chase Sapphire Reserve — Earn 60,000 Chase Ultimate Rewards points after you spend $4,000 on purchases in the first three months of account opening
  • Chase Freedom(No longer open to new applicants) Earn a $150 bonus (15,000 Chase Ultimate Rewards points) after you spend $500 on purchases in the first three months of account opening
  • The Hilton Honors American Express Aspire Card — Earn 150,000 Hilton points after you spend $4,000 on purchases in the first three months of account opening. Terms apply.
  • Hilton Honors American Express Surpass® Card — Earn 130,000 Hilton Honors Bonus Points after you spend $2,000 in eligible purchases on the Card in the first 3 months of Card Membership. Plus, you earn an additional 50,000 points after spending a total of $10,000 in purchases on the card in the first six months. Terms apply.
  • Marriott Bonvoy Brilliant™ American Express® CardEarn 125,000 bonus Marriott Bonvoy points after you use your new card to make $5,000 in purchases within the first three months. Plus, earn up to $200 in statement credits for eligible purchases at U.S. restaurants within the first six months of card membership. Offer ends 5/12/2021.

The information for the Hilton Aspire Amex card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

They also spent five years accumulating a truly impressive 200k+ United miles via actual butt-in-seat flying, in addition to frequent use of the United MileagePlusX app and bonuses from rental cars. This enabled them to fly EVA Air’s phenomenal business-class product for the long journey from San Francisco to Singapore.

(Photo courtesy of Tom Ainsworth.)

As if that weren’t amazing enough, they also snagged United saver-award space on Singapore Airlines for the flight from Singapore to Male, and even better, cashed in their Alaska Airlines miles (earned via welcome bonuses, flying and shopping portal bonuses) for flights from Male to San Francisco (with a free stopover in Dubai) in Emirates first class:

All told, they spent just under 800,000 points for flights and hotels. If that seems suspiciously low to you, that’s because it is. Tom and his wife are no newbies, and they managed to squeeze incredible value from travel rewards credit card perks to extend their stay. Using the annual free weekend night offered by the Hilton Honors Aspire Card they both applied for, and a third free weekend night earned by spending $15,000 on the Hilton Honors Surpass Card, they managed to stay five whole nights while spending only 190,000 points. That’s an incredible redemption, especially at a hotel that regularly goes for more than $1,000 per night.

Photo courtesy of Tom Ainsworth.
(Photo courtesy of Tom Ainsworth)

They also used the annual statement credits offered by the Marriott Bonvoy Brilliant Card to pay for the JW Marriott in Dubai, turning their cash stay (which earned them bonus points and elite credits) into a completely free affair.

Photo courtesy of Tom Ainsworth.
(Photo courtesy of Tom Ainsworth.)

Here’s the breakdown of the points they spent:

Program Points used Current TPG valuation in cents per point
United Airlines 237,000 1.30
Alaska Airlines 300,000 1.80
Hilton Honors 190,000 0.60
Chase Ultimate Rewards 43,000 2.00

Here’s how they redeemed them:

Flights City Airline Class of service Points used Comments
Flight San Francisco to Singapore EVA Air Business 180,000 United Airlines miles
Flight Singapore to Male’ Singapore Airlines Business 100,000 United Airlines miles
Flight Male’ to Dubai to San Francisco Emirates First 300,000 Alaska Airlines miles


Hotels Location Name Points used Comments
Paid hotel Singapore Conrad Centennial Singapore N/A Out of pocket $1,455 (four nights)
Hotel reward Maldives Conrad Maldives Rangali 190,000 95,000/night (two nights)
Credit card rewards Maldives Conrad Maldives Rangali N/A Covered with Aspire and Surpass free weekend nights (three nights)
Credit card rewards Dubai JW Marriott Marquis Hotel Dubai N/A Covered with the Bonvoy Brilliant annual statement credits (two nights)

Tom and his wife put together a truly memorable vacation, from their awe-inspiring Emirates redemption to the five nights in their overwater bungalow. And clever use of hotel credit cards, dedicated mileage earning and credit card welcome bonuses meant that this high-end vacation was nearly free. Inspirational!

Featured photo courtesy of Tom Ainsworth.

Updated on 4/8/2021

Chase Sapphire Preferred® Card

WELCOME OFFER: 80,000 Points


CARD HIGHLIGHTS: 2X points on all travel and dining, points transferrable to over a dozen travel partners

*Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.

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More Things to Know
  • Earn 80,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $1,000 when you redeem through Chase Ultimate Rewards®. Plus earn up to $50 in statement credits towards grocery store purchases within your first year of account opening.
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  • Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards®. For example, 80,000 points are worth $1,000 toward travel.
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