Every January, Ben Sorkin and Max Teirstein embark on an adventure to celebrate their anniversary—a “big winter trip,” as they call it. After meeting on a dating app in January 2021, the two quickly bonded over their love of exploration, even if their first pandemic-era dates were limited to socially distanced hikes and home-cooked meals.
To kick off 2025, the then-Boston-based couple searched for something rugged, outdoorsy, and on the opposite side of the globe. Sorkin, the more points-savvy of the two, secured a week-long journey to New Zealand and Australia.
While the total cash cost would have been more than $13,000—they flew on business class flights and stayed in luxury hotels—the couple spent a fraction of that. Here’s how they did it.
How They Booked It
Sorkin was strategic with how he booked both the flights and the hotels for this winter trip.
The Flights
The Flights by the Numbers
- The destination: Auckland and Sydney
- Points breakdown: 60,000 American AAdvantage miles for American Airlines business class from Los Angeles to Auckland + 80,000 Avianca LifeMiles for United Airlines business class from Sydney to San Francisco
- Redemption value: About $12,000
- The total actually spent on flights: $2,200
Instead of deciding where they wanted to go first, Sorkin built their trip around a single flight deal. When he got the email from Thrifty Traveler Premium, a subscription service that alerts users to award flight availability, he knew this deal was the one.
“We saw a unicorn offer for American business class from LA to Auckland for about 60,000 miles one-way,” said Sorkin. “I already had enough miles in my AAdvantage account, and we bought some miles for Max for around $1,600, which still felt like a steal for the experience.”
Generally, purchasing airline miles or hotel points isn’t worth it—with one major exception. “Topping up,” or acquiring additional points or miles to reach a specific redemption goal, can be a sensible approach. “Buying miles can sometimes still be cheaper than paying cash, especially when redeeming for long-haul business class seats,” Sorkin added.
For the return business-class flight from Sydney to San Francisco, Sorkin redeemed 80,000 Avianca LifeMiles per person, thanks to another email alert from Thrifty Traveler Premium.
While Avianca is a Colombian airline, you can book flights on the carrier’s partners (both Avianca and United Airlines are part of the Star Alliance). In this case, Sorkin booked United business class using Avianca miles, which was less pricey than booking directly through United.
Leveraging the power of transfer partners is a key points and miles hack. In this case, Avianca LifeMiles is a partner of most of the major transferable point programs (American Express Membership Rewards, Chase Ultimate Rewards, Capital One Miles, Citi ThankYou Rewards, and Bilt Rewards).
The couple also paid cash for separate flights from Boston to Los Angeles (and for the return from San Francisco to Boston). Since award availability for international flights is often limited, it can make sense to purchase standalone flights, in cash, to “position” to and from the long-haul legs. And instead of burning even more points for the domestic segments, Sorkin and Teirstein took a more balanced approach: they spent some cash but also redeemed points where they could get the most value. In total, they spent about $300 per person for these two domestic legs.
Vidhya Raithatha/Hyatt
The Hotels
The Hotels by the Numbers
- The destination: Auckland and Sydney
- Points breakdown: 43,000 World of Hyatt points for two nights at the Park Hyatt Auckland + 50,000 Capital One points for two nights at the Intercontinental Sydney
- Redemption value: $1,600
- The total actually spent on hotels: $0
For their stays, the couple also booked hotels using points. At the time, the Park Hyatt Auckland required 43,000 World of Hyatt points for a two-night stay. The Intercontinental Sydney offered a room for 50,000 Capital One points (or $500 in cash) through Capital One Travel, a platform only open to Capital One cardholders.
How to Book It Yourself
To redeem Hyatt points, you need a World of Hyatt account. Conveniently, two of the best credit card programs in the space—Chase Ultimate Rewards points and Bilt Rewards points—transfer to the Hyatt program instantly, at a one-to-one ratio. To move Chase or Bilt points to travel partners, log in to your account, navigate to the respective portal, and select the option to transfer. For first-timers, you’ll also need to enter your loyalty program account information.
What the Experience Was Like
The trip kicked off in style as Sorkin and Teirstein flew to Auckland in American Airlines’ lie-flat business class. “I was honestly impressed. The food was better than United’s, and the seat was great,” said Sorkin. “Also, Max and I finally got to sit in a paired center seat setup—which I never do when I’m flying solo.”
To add to the celebratory nature of their South Pacific adventure, they landed on Sorkin’s birthday. The couple hit the ground running, driving straight to the Bay of Islands; here, the couple booked accommodations with cash.
After a few nights exploring the area, they returned to Auckland for a stay at the Park Hyatt.
“The hotel was stunning and our bathroom alone was giving spa vibes. Huge rain shower, a soaking tub, fancy bath products—we loved it,” said Sorkin. “Plus, a major tennis tournament was happening nearby and we just kind of stumbled into it.”
Finally, they traveled to Sydney and checked into the Intercontinental, which featured a rooftop restaurant and views of the Opera House. “We had wine overlooking the harbor, watched ferries float by, and even took a ferry to the Sydney Zoo,” said Sorkin. “It was the perfect base for exploring the city.”
The journey ended with a United business class flight back to the U.S., where the couple got cozy in the airline-provided pajamas. “On the way back, we realized we had just literally skydived in New Zealand from 15,000 feet, and we were now cruising at 35,000. It really put things in perspective.”
Points and Miles Tips for Travelers
Sorkin credits the success of the trip to a few key strategies.
- Use Deal Alert Services: Thrifty Traveler Premium was “gold,” according to Sorkin. “We wouldn’t have found the deals otherwise.”
- Don’t Fear Buying Points: “Buying miles can still be cheaper than paying cash—especially for long-haul business class.”
- Be Flexible with Positioning Flights: “We couldn’t find great East Coast options, so flying to the West Coast first and stitching things together helped a lot.”
“It wasn’t just a trip,” said Sorkin. “It felt like we were building a new chapter of our relationship—flying through time zones, soaking in views, eating amazing food, and making each other laugh the whole way. And doing it all in style made it even more memorable.”
