inauspicious positioning

Once in a while an amazing flight deal comes along, one that’s almost impossible to pass up. It is because of one of these amazing deals that I’m about to embark on a journey that I’ve always wanted to do, a journey that circumnavigates the globe.


Back in May I received a message from my friend Tim asking if I wanted to get in on an amazing flight deal. As part of this deal we would be able to fly from New York to Italy and from Prague to Singapore for under $325. It was a deal that was too good to pass up, but it would take a good deal of planning to fill in the holes in the itinerary. In travel blog parlance, we’d need to take what’s called a ‘positioning flight,’ a trip that we’d need to make solely to take advantage a fare deal.

For our positioning flight we decided that we would take a red-eye flight to New York, leaving California late at night and arriving in New York the morning before our scheduled international flight. Then we’d spend a night relaxing and eating in New York, before flying out to Europe. In Europe we would be taking the trains from Milan to Prague, stopping in Venice and Vienna along the way. From Prague we had our ticketed flight to Singapore, which we’d use as a base from which to take discount Asian airlines to Phuket (Thailand) and Siem Reap (Cambodia.) The plan was then for Tim to fly home from Cambodia, and I’d continue on using airline miles to visit family in Korea for a little over a week before flying back home. It seemed like a good plan, but all hinged on that initial positioning flight to New York.

Our itinerary seemed like it would have an inauspicious start when we received an email from US Airways stating that our flight had been rescheduled. Instead of being a red-eye flight arriving the morning after our departure, the flight had been rescheduled to arrive very late at night the same day. This would mean that either we’d need to spring for another night in a hotel or we’d need to spend the night at the airport. Since both of us are kinda cheap, we decided that we’d just rough it on the airport floor.

Luckily we didn’t have to rough it at the airport. Tim had some other friends who had gotten in on the same flight deal as us, and luckily for us they weren’t as cheap as us. They had booked a hotel for the night, and they were fine with us crashing on their hotel room floor. They were staying at the Marriott in Queens, and when I checked my email I saw that lo and behold I had a Marriott free room certificate.

My Marriott credit card had just been charged for its annual fee, and as part of that deal I get a free room certificate good for up to a category 5 hotel room. When we arrived at the Marriott at Queens I asked what category their hotel fell under, to which they replied category 5. What seemed like an inauspicious start to our trip wasn’t looking too bad anymore. In fact, it seemed like things were starting out on an awesome note! But when I called the Marriott reservations line, I found that the front desk had been mistaken, the Marriott in Queens was actually a category 7, so I wasn’t able to use the certificate. So we still ended up on the floor in Tim’s friend’s hotel.

This was again looking like an inauspicious sign for the rest of the trip. If we had this much trouble with flights and hotels before even leaving the country, things would only be more difficult after we leave the country, since communication using our cell phones may not be possible. And to make things even more complicated, for most of our trip we’d be using AirBnb instead of hotels, and I figured if we had this much trouble with a hotel, AirBnb might be even worse, since we may have trouble getting in touch with our hosts. And if the huge US Airways was able to reschedule a flight for a different day, wouldn’t a small discount airline in Asia be even more unreliable? I’m not usually one to worry, but these thoughts, especially the worries about communicating with our AirBnb hosts, would stay on the back of my mind throughout our crazy round the world trip.

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