Anatomy of an award trip: Winter jaunt to Italy

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This is another entry in my occasional series, "anatomy of an award trip."

Background: the fuel dump

Back in May, an apparently-longstanding fuel dump broke into the open on Flyertalk. Low base fares on Alitalia-coded flights meant it was possible to book tickets from New York City to Milan for between $100 and $250, as long as you added a leg at the end of the trip from one of a number of European cities to Asia. The fuel dump was bookable for a huge range of dates through the end of the flight schedule, so folks rushed to book summer, fall, and spring trips before the mistake was caught and fixed.

Since my partner abides by an academic's calendar, my only options were to book something in January or speculatively for next Spring. I booked a few one-ways for various available dates and waited for her to get home.

We ended up settling on an early-January flight that priced out at $233.20 each.

Once we settled on a date for the outbound flight to Milan, I naturally had to put together the rest of the trip.

Getting there: Upper Midwest to New York City

Since the fuel dump was booked out of New York City, first we had to get there.

This part was easy, since there was low-level award availability on American Airlines through Chicago, so I booked 2 tickets for 12,000 British Airways Avios and $5 each. While Avios are rightly praised for short, non-stop flights, I found that even with the connection in Chicago, the flight priced out cheaper than it would have using any other currency (plus I still have too many Avios from my January credit card application).

It's true I could have saved 9,000 Avios by driving to Chicago instead, and if our connection looks hazardous due to weather conditions we may still end up having to do that. But if the skies are clear, I'd much rather fly than drive.

Total cost: 24,000 Avios and $10. Total value: $300. Value per point: 1.2 cents per Avios.

While this would be considered by some travel hackers as an embarrassingly low redemption for Avios, I had way too many Avios in my account and was eagerly searching for a way to redeem them. Remember: the least valuable mile will always be the one you don't redeem.

Getting back: Rome to Chicago

While I briefly considered popping up to Budapest and making the second flight to Tokyo, my partner needs to get back and I realized that I'm already locked into a potentially expensive 9 days of eating and drinking all over Italy, so I started looked for return flights from Milan and Rome.

There were a lot of options for the return, but I ended up settling on a non-stop flight on US Airways from Rome to Philadelphia followed by a short hop up to Chicago. Since there was low-level availability and the flights are during American Airlines' "low" European award season, I was able to book the tickets for 20,000 AAdvantage miles and $69.60 each.

I briefly considered using Iberia Avios to connect in Madrid, but while Iberia charges lower fuel surcharges on their own flights than British Airways does, they're still not cheap: $352 compared to BA's $506.

Total cost: 40,000 AAdvantages miles and $139.20. Total value: $3,707 (the price of the cheapest flight that doesn't involve overnight stays). Value per point: 8.91 cents per AAdvantage mile.

Note: this is the kind of absurd award valuation you get when you value particular awards independently of the trips they're a part of. A round-trip flight to Milan in January costs $1,162; the fact that one-way flights are outrageously priced is interesting, but not dispositive when deciding whether to purchase a round-trip flight or redeem miles for a one-way.

Using that $1,162 price, you can arrive at a much more realistic 2.67 cents per point (saving $854.20 while spending 12,000 Avios and 20,000 AAdvantage miles per ticket).

Staying there: Italian vacation

I've done Italy before, but this is my partner's first time so I'm still in the process of putting together a trip that's going to let her see as much as possible. Here's the rough outline so far — it would be great if readers could chime in with their own Italian experiences!

  • Park Hyatt Milan, 1 night. 30,000 Hyatt Gold Passport points, located right in the center of town at the Duomo;
  • Hilton Molino Stucky Venice, 1-2 nights. 50,000 Hilton HHonors points per night, and I've heard great things from a reader about this property;
  • AC Hotel Bologna, 1 night. 1 Category 4 Marriott Rewards certificate;
  • Hilton Florence Metropole, 1 night. 30,000 HHonors points;
  • Radisson Blu es. Hotel, 2 nights, 66,000 Club Carlson points (for a premium room award – why not, I have the points);
  • Renaissance Naples Hotel Mediterraneo, 1 night. 1 Category 5 Marriott Rewards certificate;
  • Hilton Sorrento Palace, 1 night. 30,000 HHonors points.

Conclusion

It turned out that I was able to build a very reasonable award trip around a very cheap flight between New York City and Milan. But that won't always be the case, and it's worth pointing out that once you've booked a mistake fare like this, there's no shame in walking away from it if you can't put together an itinerary that makes sense for you and your travel companions.