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My 40-Hour Trip from San Francisco to New York

a view of clouds from an airplane window

***This is part 1 of my “Plane-cation” trip report detailing a recent trip from San Francisco to New York, via Hong Kong***

1. Introduction
2. Singapore Airlines First Class San Francisco to Hong Kong
3. Cathay Pacific First Class Lounges: The Pier and The Wing
4. Cathay Pacific First Class Hong Kong to New York
5. Eating NYC – Bouley, Donuts, and Pizza
6. JetBlue Mint Class New York to San Francisco
7. First Class Showdown: Singapore Airlines vs. Cathay Pacific

“How was your flight?”

It’s a pretty standard question that you may get asked after arriving at your destination. But in this case, I wasn’t really sure how to answer it.

All of the major U.S. airlines have a direct flight for the trans-continental journey from San Francisco to New York, and most of them even feature a special premium product for that route. The direct flight will take about six hours, plus or minus a half hour depending on the direction you’re flying, and even with a connection you can still get from coast to coast in less than ten hours.

But for this particular trip from San Francisco to New York, I decided to take the scenic route. Well that’s probably a huge understatement, since I literally flew halfway across the world on a journey that took 40 hours.

I had outlined the rationale for turning my stay-cation into a plane-cation, which was primarily a result of wanting to unplug for some “me time” and to burn more of my American Airlines miles before the upcoming devaluation. As I thought about how crazy this idea was, I had almost pulled the plug several times leading up to the trip, but I’m glad I went through with it since I loved every minute of the adventure.


Breaking down the 40-hour journey

The first leg of the trip was the 14-hour flight Singapore Airlines First Class flight from San Francisco to Hong Kong. As luck would have it, this would also be the first time that I got to sample their new First Class product.

singapore airlines first class san francisco to hong kong new seat

My 9-hour layover at Hong Kong International Airport was a whirlwind of eating where I managed to get all of my favorite Chinese foods, including dim sum, wonton noodles, egg tarts, and roast pork, without even leaving the airport and all for free. The majority of the time was spent at Cathay Pacific’s newly renovated The Pier First Class lounge which featured The Retreat day rooms. I occupied one of these for the duration of my visit, while ducking out to eat, shower, and massage as needed.

cathay pacific the pier first class lounge the retreat

The return flight to New York was in Cathay Pacific First Class, which I had not flown in over two years. I had forgotten how amazing this First Class product was, highlighted by the excellent food and service.

cathay pacific first class hong kong to new york first class seat

While I had flown Singapore Airlines and Cathay Pacific’s First Class products before, trying each one within the same day helped me focus on the comparison between these two Asian heavyweights which I plan summarize at the end of this trip report.

After a couple days of nonstop eating in NYC, including the best cream puffs I’ve ever had from Bibble and Sip, it was time to head home where I tried JetBlue’s Mint for the first time. In short, in my opinion this is the best trans-continental U.S. product available today.

bibble and sip nyc earl grey match cream puffs

I had outlined here what I was hoping to do during my time off, and here’s a breakdown of what I actually did during those 40 hours:

  1. Sit around the house all day in my pajamas
    • Other than the 9-hour layover in the airport lounge, happy to confirm that the remaining time was spent in pajamas
  2. Catch up on all the TV shows and movies that I’ve missed
    • Surprisingly only watched three movies – highlighted by The Hateful Eight, low-lighted by The Transporter Refueled, and with The Intern falling somewhere in between
  3. Surf the internet and watch Youtube videos for hours on end
    • No internet on either of the flights, which was probably a blessing in disguise since I was able to fully disconnect, but was able to keep in touch as needed during my layover
  4. Eat and drink whatever I want since I’m technically on vacation
    • Between the eating on the flights and the constant eating at the lounges, it’s fair to say that I arrived in New York significantly heavier than when I left just a day and a half earlier. As an added bonus, on my Cathay flight I was introduced to Banoffee pie which I have been obsessed with ever since
  5. Sleep 8-12 hours a day including countless naps
    • I arrived in NYC fresher and more well-rested than if I had flown directly. I slept for 9 hours on the outbound leg to Hong Kong, and 10 hours on the return to New York. That’s actually one reason that I didn’t watch that many movies, since that’s 19 hours of sleep out of the 30 hours of total flight time. It helped that both flights were red-eyes, meaning that I didn’t have to disrupt my body clock

cathay pacific first class hong kong to new york banoffee pie


How to plan your own plane-cation

So would I do another plane-cation? Absolutely. If you’re looking to do the same, here are my top 7 tips:


  1. There’s no denying that it’s an extremely indulgent way to burn your miles, so make sure that you’re truly OK with the idea of sitting on a plane and essentially flying in a circle
  2. Use the time to unplug and really enjoy some “me time”, even if wifi is available on the plane resist the urge to buy it
  3. Drink lots of water and stay hydrated, minimize booze consumption if you can help it
  4. Walk as much as possible between flights. I still registered about five miles each day for those two days by doing laps around the airport rather than just sitting around
  5. Even though I ate a lot, I avoided carbs by not touching the bread or pastries during meals which helped me feel a little less gross
  6. I know there is a lot of debate about how to “maximizie” the First Class experience, but I’d recommend going for the red-eye flights so that you can get a proper night’s sleep which will help minimize jet lag
  7. Lastly, Global entry is a big plus since I didn’t have to talk to the Customs agent and explain why I had flown across the world only to turn right back


    1. Thanks! Yes, booked everything about 1.5 weeks before when the CX F availability opened up

      1. That’s definitely the long way round to NYC. How did you manage the transit in HKG from the SQ award onto CX? Were you able to get the new boarding pass issued in the transit area?

        1. I had checked in online for the CX flight and was able to get the boarding pass in the transit area, same as if I was connecting onward anywhere else from HKG. No questions asked!

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