Fuck I am finally flying somewhere it’s been forever

It’s been a while. No, I didn’t die. At least on the outside.

I was dying on the inside, though, until about 72 hours when a friend of mine who’s studying in Europe asked me if I wanted to come over and go somewhere. I’m like, “Sure, where?” And he said “how about Moldova?” Because he’s an awesome traveler, so of course he’d want to go somewhere other people don’t go.

Work is work, and I couldn’t leave any sooner than Thursday night, and I gotta be back after the long weekend, so there were parameters. First I had to figure out where the hell Moldova is. It’s far Eastern Europe, wedged between Romania and Ukraine (and the de facto, but unrecognized, state of Transnistria).

Then I had to kick all my shit into gear to try to get there. Of course I wanted to fly biz. I yanked up Google Flights to see what airlines go there, and it was pretty much all Star Alliance: Lufthansa, Turkish, Singapore, Austrian, with a couple of one-stop options (rather than two).

I felt my United love shine through because that’s where I have the mostest points, and their web site made it pretty easy to find whether there was biz saver award availablity from NYC -> KIV. There weren’t a whole lot of biz saver outbound options on Friday except on Austrian…except that I’d have to fly to Chicago to catch that. I decided that fuck it, I’d just do that, for 70,000 United miles. Lotta extra travel, but the econ options only got me in a couple hours sooner, and I’d rather just stretch out and enjoy whatever liqueurs were on offer. Plus I could check out the Polaris lounge in Chicago.

For the return I was able to book Lufthansa business, one stop to JFK through Frankfurt — perfect. And on the 747! I’ve always wanted to fly on the top bubble area of a 747, and now I’m gonna get to before they all go away. Again for 70,000 United miles. I transferred some Chase points to get enough.

So, that seemed easy, except I have to make everything difficult, so I took advantage of United’s 24-hour cancel policy by 23 hours later rebooking the exact same flights and canceling the original so I still had options. I don’t like being pinned down.

The thing that was gnawing at me is that I really wanted to get there on Friday, not Saturday. I wanted to leave Thursday, but I had a 5:30 PM appointment with a new client, and they didn’t want to move it to an earlier time. I thought about moving them, but if I was somebody’s new client and found out I got bumped because someone wanted an extra day in Moldova for a last-minute joyride, I’d be pissed, so I decided to be a fucking professional and suck it up.

But I still wanted to get in Friday. There had to be a way. (My feeling in life is that there is always a way — it’s just a question of how much time and expense and headache is required to find and execute it.) There had to be some flight that left Thursday night and didn’t have an insane layover so I could get there on Friday. But none of the programs where I have points (or to where I can transfer points) had anything to offer me all the way to KIV. I mean, I was flying to fucking Chisinau, Moldova. It ain’t London.

And then I had that moment: What if  forgot about trying to route to KIV, and just worried about getting to a major city in Europe, and then just paid for whatever carrier could get me to where I was going from wherever I was, on a separate ticket? I’m a genius.

Next thing I did was find the website for KIV airport. It helpfully had a list of arriving flights for the next three days. So I looked in the time range I wanted (like 2 PM – 8 PM), and ignored any flights from locations that were obviously out of the way from the US, like Moscow, or from places that couldn’t be gotten to nonstop from the US, like Bucharest.

So now I had a list of arrival times and origin cities. Candidates were Paris, Rome, Frankfurt, Geneva, Vienna, Warsaw, Istanbul. I went on Google Flights to search each one’s nonstop options to Chisinau, so that I had the departure times.

Now I had to figure out if there were any flights that a) departed after 9 PM from NYC nonstop to any of those cities, b) arrived with at least 2 hours to connect to the next flight, and c) didn’t cost an obscene amount of cash or miles.

Based on departure and connection time, Warsaw, Vienna, and Geneva were off the list. That left Paris-CDG (Air France, Primera, XL), Frankfurt (Lufthansa, Singapore), Rome (Alitalia, Norwegian), and Istanbul (Turkish).

Just for laughs, I looked at the cash prices for these in Google, and the real airlines were around $3K for economy, so I said no thanks. The low-cost carriers like Primera, XL, and Norwegian had options for like $1000-$1200, and then I suddently thought how happy I would be flying in a middle seat on a single-aisle plane, which is to say that I could not absolutely rule out arrest, or burial, upon landing. And it was certainly more cash than I wanted to spend. Plus, all those cheapie airlines suck to try to book with Chase points; you have to call the dumb outsourced Chase travel people and have them try to do it for you. Say what you will about Amex, at least they have their own travel agency.

So now it was time to try to get a miles ticket. And this is why redeeming miles takes so fucking long. It took all the above just to get here, and now the real work begins, because there ain’t no Kayak for award flights.

There’s no way to get miles into Lufthansa and Turkish from Chase or Amex, and I didn’t have enough SPG/Marriott. But they’re both Star Alliance, meaning United partners, so I searched on United hoping they’d let me book them as a United ticket, but…no. There might have been non-saver options: 70,000 miles for economy, or 155,000 for business, but I wasn’t gonna blow my precious points like that. And then I tried AeroPlan, to which I can transfer from Amex…and no dice there, either. Sucky.

I had hope for Singapore, especially to try to fly them in biz or first. Or anything, really. Both Chase and Amex transfer to Singapore. But Singapore had no award tickets in any cabin. Also sucky. Air France has direct transfers from Chase and Amex as well, but they shrugged me off, too.

That left Alitalia, which I almost accidentally overlooked when I first made my list. And it really had a flight in the sweet spot — 9:30 PM departure, and a nice 3.5 hour transfer in Rome, which should be enough buffer to deal with a massive customs line or delays or whatever.

And, amazingly, after being denied by every other dumb airline…Alitalia had one lonely saver economy award seat left for me, for a reasonable 30,000 miles. I contemplated whether I was willing to, you know, fly economy just so I could arrive a day earlier, but at least it was an Airbus 330, which is a widebody, double-aisle plane. Less claustrophobia, because there are only two seats on the sides, and four in the middle.

I said fuck it, let’s just do it. I transferred the 30,000 Amex points to Alitalia, booked the ticket, and then saw what was gloriously revealed to me for my efforts: tons of open seats in economy. I might not die. I might not have a seat neighbor I might even get a row to myself in the middle, if I’m lucky, and, you know, lie flat.

I booked the Alitalia flight, and then booked my separate flight on world renowned Air Moldova. That one I probably could have or should have booked on the Chase portal, but I used Orbitz, because Orbitz gives you 24 hours to change your mind, regardless of airline, plus I’d rather save the points and do better than 1.5 cents each for them.

Also…Air Moldova. I figured if I needed to call in for anything, Orbitz might have slightly more of a clue. It was only $149, so I just paid cash and called it a day. Of course I put it, and my award ticket taxes/fees on the other flights, on my Citi Prestige, which offers expense reinmbursement if a flight is delayed more than three hours. (Well, until July 29, when Citi kneecaps the Prestige again, by raising the delay requirement to six hours, just like their competition offers. Way to win the race, guys! That’s also right around my anniversary date, conveniently enough, if you see where I’m going with that. 4th night free is all that card will have left, and I’m not sure that’s quite enough, in my case.)

Finally, I cancelled the original United/Austrian flight out. (But I definitely kept my flight back on Lufthansa, in business. This is why I book separate one-way itineraries.)

All I can say is that Moldova had better be fucking awesome! Although it really doesn’t matter. It’s somewhere, in the world, far from here. I’m already kinda satisfied.

3 thoughts on “Fuck I am finally flying somewhere it’s been forever

  1. Jack

    Really great and interesting walk through your thinking and what it actually takes to get the best deal for your miles. Would love to hear how Moldova was when you get back (I’d actually like to visit it and Eastern Europe), as well as hear how your flights were on Alitalia and “world renowned Air Moldova” (yeah, good luck with that). Hope you have a great trip.

  2. Tom

    Thank you for finally starting to post again, I very much missed your posts over the last few months and I feel like my life is once again complete now that you have returned. Please don’t ever leave us again, you are the best travel blogger by far!!!


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