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TPG Reader Hall of Fame: The ultimate luxury vacation

Oct. 25, 2019
6 min read
ConradMaldivesWatertaxi
TPG Reader Hall of Fame: The ultimate luxury vacation
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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)

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)

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

  • Alaska Airlines Visa Signature® credit card — Earn 40,000 bonus miles plus Alaska's Famous Companion Fare; from $121 ($99 fare plus taxes and fees from $22) when you make purchases of $2,000 or more within the first 90 days of opening your account.
  • Chase Sapphire Reserve — Earn 50,000 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 purchases on the Hilton Honors American Express Surpass Card in the first 3 months of Card Membership. Plus, you can earn an additional 50,000 Hilton Honors Bonus Points after you spend a total of $10,000 in purchases on the Card in the first 6 months. Terms apply.
  • Marriott Bonvoy Brilliant™ American Express® Card — Earn 75,000 bonus points after you spend $3,000 in purchases within the first three months of card membership. Plus, earn up to $200 in statement credits for eligible purchases made on your new card at U.S. restaurants within the first six months of card membership.

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.

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(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.)

Here's the breakdown of the points they spent:

ProgramPoints usedCurrent 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:

FlightsCityAirlineClass of servicePoints usedComments
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
HotelsLocationNamePoints usedComments
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!

Updated on 11/3/21.

Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

TPG featured card

Best for dining at restaurants
TPG Editor‘s Rating
4 / 5
Go to review
Apply for American Express® Gold Card
at American Express's secure site

Rewards

1 - 4X points

Intro offer

As High As 100,000 points. Find Out Your Offer.

Annual Fee

$325

Recommended Credit

Excellent to Good

Why We Chose It

There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits. (Partner offer)

Pros

  • 4 points per dollar spent on dining at restaurants worldwide and U.S. supermarkets (on the first $50,000 in purchases per calendar year; then 1 point per dollar spent thereafter and $25,000 in purchases per calendar year; then 1 point per dollar spent thereafter, respectively)
  • 3 points per dollar spent on flights booked directly with the airline or with amextravel.com
  • Packed with credits foodies will enjoy
  • Solid welcome bonus

Cons

  • Not as useful for those living outside the U.S.
  • Some may have trouble using Uber and other dining credits
  • You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $6,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
  • Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
  • Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
  • Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
  • Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
  • Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
  • $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
  • $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
  • $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
  • $120 Dining Credit: Satisfy your cravings, sweet or savory, with the $120 Dining Credit. Earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, and Five Guys. Enrollment required.
  • Explore over 1,000 upscale hotels worldwide with The Hotel Collection and receive a $100 credit towards eligible charges* with every booking of two nights or more through AmexTravel.com. *Eligible charges vary by property.
  • No Foreign Transaction Fees.
  • Annual Fee is $325.
  • Terms Apply.
Apply for American Express® Gold Card
at American Express's secure site
Terms & restrictions apply. See rates & fees
Best for dining at restaurants
TPG Editor‘s Rating
4 / 5
Go to review

Rewards Rate

4XEarn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
4XEarn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
3XEarn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
2XEarn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
1XEarn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
  • Intro Offer

    As High As 100,000 points. Find Out Your Offer.
  • Annual Fee

    $325
  • Recommended Credit

    Excellent to Good

Why We Chose It

There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits. (Partner offer)

Pros

  • 4 points per dollar spent on dining at restaurants worldwide and U.S. supermarkets (on the first $50,000 in purchases per calendar year; then 1 point per dollar spent thereafter and $25,000 in purchases per calendar year; then 1 point per dollar spent thereafter, respectively)
  • 3 points per dollar spent on flights booked directly with the airline or with amextravel.com
  • Packed with credits foodies will enjoy
  • Solid welcome bonus

Cons

  • Not as useful for those living outside the U.S.
  • Some may have trouble using Uber and other dining credits
  • You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $6,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
  • Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
  • Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
  • Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
  • Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
  • Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
  • $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
  • $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
  • $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
  • $120 Dining Credit: Satisfy your cravings, sweet or savory, with the $120 Dining Credit. Earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, and Five Guys. Enrollment required.
  • Explore over 1,000 upscale hotels worldwide with The Hotel Collection and receive a $100 credit towards eligible charges* with every booking of two nights or more through AmexTravel.com. *Eligible charges vary by property.
  • No Foreign Transaction Fees.
  • Annual Fee is $325.
  • Terms Apply.