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Each January, Ben Sorkin and Max Teirstein embark on an journey to have a good time their anniversary—a “massive winter journey,” as they name it. After assembly on a courting app in January 2021, the 2 rapidly bonded over their love of exploration, even when their first pandemic-era dates had been restricted to socially distanced hikes and home-cooked meals.
To kick off 2025, the then-Boston-based couple looked for one thing rugged, outdoorsy, and on the other aspect of the globe. Sorkin, the extra points-savvy of the 2, secured a week-long journey to New Zealand and Australia.
Whereas the overall money value would have been greater than $13,000—they flew on enterprise class flights and stayed in luxurious motels—the couple spent a fraction of that. Right here’s how they did it.
How They Booked It
Sorkin was strategic with how he booked each the flights and the motels for this winter journey.
The Flights
The Flights by the Numbers
- The vacation spot: Auckland and Sydney
- Factors breakdown: 60,000 American AAdvantage miles for American Airways enterprise class from Los Angeles to Auckland + 80,000 Avianca LifeMiles for United Airways enterprise class from Sydney to San Francisco
- Redemption worth: About $12,000
- The whole really spent on flights: $2,200
As an alternative of deciding the place they needed to go first, Sorkin constructed their journey round a single flight deal. When he bought the e-mail from Thrifty Traveler Premium, a subscription service that alerts customers to award flight availability, he knew this deal was the one.
“We noticed a unicorn provide for American enterprise class from LA to Auckland for about 60,000 miles one-way,” stated Sorkin. “I already had sufficient miles in my AAdvantage account, and we purchased some miles for Max for round $1,600, which nonetheless felt like a steal for the expertise.”
Typically, buying airline miles or resort factors isn’t price it—with one main exception. “Topping up,” or buying further factors or miles to succeed in a particular redemption aim, could be a smart strategy. “Shopping for miles can typically nonetheless be cheaper than paying money, particularly when redeeming for long-haul enterprise class seats,” Sorkin added.
For the return business-class flight from Sydney to San Francisco, Sorkin redeemed 80,000 Avianca LifeMiles per individual, thanks to a different electronic mail alert from Thrifty Traveler Premium.
Whereas Avianca is a Colombian airline, you possibly can ebook flights on the service’s companions (each Avianca and United Airways are a part of the Star Alliance). On this case, Sorkin booked United enterprise class utilizing Avianca miles, which was much less expensive than reserving instantly by means of United.
Leveraging the facility of switch companions is a key factors and miles hack. On this case, Avianca LifeMiles is a accomplice of a lot of the main transferable point programs (American Specific Membership Rewards, Chase Final Rewards, Capital One Miles, Citi ThankYou Rewards, and Bilt Rewards).
The couple additionally paid money for separate flights from Boston to Los Angeles (and for the return from San Francisco to Boston). Since award availability for worldwide flights is commonly restricted, it will possibly make sense to buy standalone flights, in money, to “place” to and from the long-haul legs. And as a substitute of burning much more factors for the home segments, Sorkin and Teirstein took a extra balanced strategy: they spent some money but additionally redeemed factors the place they might get probably the most worth. In whole, they spent about $300 per individual for these two home legs.
Vidhya Raithatha/Hyatt
The Resorts
The Resorts by the Numbers
- The vacation spot: Auckland and Sydney
- Factors breakdown: 43,000 World of Hyatt factors for 2 nights on the Park Hyatt Auckland + 50,000 Capital One factors for 2 nights on the Intercontinental Sydney
- Redemption worth: $1,600
- The whole really spent on motels: $0
For his or her stays, the couple additionally booked motels utilizing factors. On the time, the Park Hyatt Auckland required 43,000 World of Hyatt factors for a two-night keep. The Intercontinental Sydney supplied a room for 50,000 Capital One factors (or $500 in money) by means of Capital One Journey, a platform solely open to Capital One cardholders.
Learn how to Ebook It Your self
To redeem Hyatt factors, you want a World of Hyatt account. Conveniently, two of the most effective bank card packages within the area—Chase Ultimate Rewards factors and Bilt Rewards factors—switch to the Hyatt program immediately, at a one-to-one ratio. To maneuver Chase or Bilt factors to journey companions, log in to your account, navigate to the respective portal, and choose the choice to switch. For first-timers, you’ll additionally have to enter your loyalty program account data.
What the Expertise Was Like
The journey kicked off in type as Sorkin and Teirstein flew to Auckland in American Airways’ lie-flat enterprise class. “I used to be actually impressed. The meals was higher than United’s, and the seat was nice,” stated Sorkin. “Additionally, Max and I lastly bought to sit down in a paired middle seat setup—which I by no means do after I’m flying solo.”
So as to add to the celebratory nature of their South Pacific journey, they landed on Sorkin’s birthday. The couple hit the bottom working, driving straight to the Bay of Islands; right here, the couple booked lodging with money.
After a number of nights exploring the realm, they returned to Auckland for a keep on the Park Hyatt.
“The resort was gorgeous and our lavatory alone was giving spa vibes. Enormous rain bathe, a soaking tub, fancy tub merchandise—we cherished it,” stated Sorkin. “Plus, a serious tennis event was taking place close by and we simply sort of stumbled into it.”
Lastly, they traveled to Sydney and checked into the Intercontinental, which featured a rooftop restaurant and views of the Opera Home. “We had wine overlooking the harbor, watched ferries float by, and even took a ferry to the Sydney Zoo,” stated Sorkin. “It was the proper base for exploring the town.”
The journey ended with a United enterprise class flight again to the U.S., the place the couple bought cozy within the airline-provided pajamas. “On the best way again, we realized we had simply actually skydived in New Zealand from 15,000 toes, and we had been now cruising at 35,000. It actually put issues in perspective.”
Factors and Miles Ideas for Vacationers
Sorkin credit the success of the journey to a couple key methods.
- Use Deal Alert Providers: Thrifty Traveler Premium was “gold,” based on Sorkin. “We wouldn’t have discovered the offers in any other case.”
- Don’t Worry Shopping for Factors: “Shopping for miles can nonetheless be cheaper than paying money—particularly for long-haul enterprise class.”
- Be Versatile with Positioning Flights: “We couldn’t discover nice East Coast choices, so flying to the West Coast first and stitching issues collectively helped lots.”
“It wasn’t only a journey,” stated Sorkin. “It felt like we had been constructing a brand new chapter of our relationship—flying by means of time zones, soaking in views, consuming superb meals, and making one another snigger the entire approach. And doing all of it in type made it much more memorable.”
















































