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Thanksgiving in Grand Cayman, New Year’s in Rio and Fourth of July in Greece

ByThe Miles Professor
View of Rio de Janeiro from Corcovado
View of Rio de Janeiro from Corcovado
I love New York, but I don’t love the cold… and as soon as it starts to get even a tiny bit chilly, I start planning my little getaways to warmer weather. So last October, I started planning a Thanksgiving trip to the Caribbean and a Christmas/New Year’s trip to Rio de Janeiro.

 

The problem was my dates weren’t very flexible and I absolutely had to meet the following conditions:

  • leave for the Caribbean on Thanksgiving Thursday

  • come back Sunday after Thanksgiving (biggest travel day of the year!)

  • fly to Rio the weekend before Christmas (also a big travel weekend)

  • be back at work by January 2

I found a one-way ticket to Grand Cayman on Thanksgiving Thursday for $130 and thought that would be a great place to start! I had never been to the Caymans… plus I knew that Starwood was having a 40% off the Westin Grand Cayman point redemptions (more on that later!) This would get me to the Caribbean so 1 out of 4 legs completed!

From Cayman and to Rio de Janeiro:

An initial search on oneworld (American Airlines alliance) and Star Alliance (United Airlines alliance) yielded the following:

  • Sunday after Thanksgiving: No saver award space from Cayman (no surprise there!!!)
  • weekend before Christmas: No saver award space to Rio
  • December 31: Saver business class ticket on United Dec 31 from Rio to NY, no saver awards on oneworld

 

Since United had the business class saver award available, at this point, I could have booked the full trip on United paying 100k for the following “round-trip”:

  1. From Cayman to Rio in economy with a “stop” for about a month in NY paying for a standard award
  2. Back from Rio to New York
Kind of roundabout...
Kind of roundabout on United Airlines…
Much better!
Much better on American Airlines!

 

…but the flight on United from Grand Cayman stops in Houston and then the flight to Rio stops in Sao Paolo and going through an out of the way airport like Houston on a Thanksgiving weekend trip just seemed like such a hassle to me!

 

American Airlines, on the other hand, had a way more convenient flight from Grand Cayman to New York with a short stop in Maimi and a daily non-stop to Rio leaving at 10:30 pm. Since American books all award trips as a one way and allows a free stopover in the North American city from where one leaves the region on transcontinental awards, I instead decided I wanted to book a “one way” trip from Cayman to Rio with a stop in New York with the following legs:

  • Cayman – Miami – New York on Sunday after Thanksgiving
  • New York – Rio direct on Saturday, Dec 22
  • COST: 54k AA miles

(an Aanytime ticket from North America to Rio costs 60k miles Citi AAdvantage Visa card holder earns you 10% rebate on redeemed miles up to 10k miles a year).

Getting back from Rio:

The ticket in business class from Rio to New York with a stop in Houston cost 50k United miles. United international roundtrips allow a stopover and two open jaws which basically allows one to tack on free or heavily discounted one ways to roundtrips. I wanted to try to combine the one way to Rio with a longer trip somewhere since I feel redeeming just a one way award leaves miles on the table!

South America to Europe in business class is 70k miles each way and New York is conveniently on the way from Rio to Europe :) I know for sure I am going to Europe in the next year as there is a potential cousin trip to Greece or I may stop by Nice to spend labor day weekend with the family. My Greece plans weren’t certain, but a date change on United is free with no destination change or $75 for a destination change. I saw the whole thing as not a huge deal if I do need to change it. I picked the following flights:

  • Rio-New York in business class on United with a stop in Houston on December 31

  • New York-Athens in business class on Lufthansa leaving evening of June 28

  • Athens-New York in economy on Austrian Airways on July 7

  • COST: 100k UA miles.

Final miles cost for all 3 trips:
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I really feel I didn’t leave any money or miles on the table there!

Summary

While I could have booked the Cayman-New York, New York-Rio, Rio-New York segments for 100k UA miles total for the first two legs in economy and the last one in business, I would have ended up with kind of inconvenient flights from Cayman and to Rio. Moreover, doing things this way, my flight in business to Europe and back in economy only end up costing me an incremental 54k AA miles ONLY. According to the United airlines award chart, it actually costs 80k UA miles for the same roundtrip!

So lesson learned: Plan ahead and combine as many trips as possible :)

Stay tuned: Arranging friends to join me in the Caymans!

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