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Thursday, June 20, 2024
HomePointsBookingHow to Book the Best Itinerary: AA, Avios, Aeroplan, Miles & Smiles,...

How to Book the Best Itinerary: AA, Avios, Aeroplan, Miles & Smiles, Flying Blue, LifeMiles, Capital One

How to Book the Best Itinerary is part of the Still The Best Trip Report.

I have been traveling on points since 2012 (see Angle Flat Lufthansa: My First Points Flight Review). I have consistently put together one insane itinerary after another (see The $77,000 Trip Heard Round the World25,000 Mile RTW Trip Including Iraq Booked!). Yet, somehow, I have failed to convince friends and family that all trips are possible if the points, not price, are right.

I now write these posts so I can celebrate my greatness. However, just in case someone else is reading, here is how I put together this stellar itinerary.

a map of the world

a table with numbers and a blue sky

a table with numbers and a blue sky a green and yellow table with black text

  1. San Juan to Tenerife: This was an easy booking. I transferred points from Amex to my Iberia Avios account with a 30% bonus. I searched SJU-TCI (see Not My Fault: Tenerife Airport, North Or South?).
  2. Tenerif to Cabo Verde: There were no convenient price/points options here. I used my Capital One Venture X to find the cheapest, most direct deal (see Can You Tell Me How to Get to Cabo Verde?).
  3. Cabo Verde to Nice, France: This was another easy booking. I again took advantage of the 30% bonus by transferring points from my Amex to British Avios account.
  4. Corsica to Paris, France: I wasn’t too upset about paying $227 to go to Corsica, but there was no way I was going to pay $459 to go from Corica to Paris. Luckily, I found availability on Air France using my FlyingBlue account. Once again, I will be flying coach on Air France (Flying Blu, Literally Depressed: DTW-CDG Air France in Coach).
  5. Paris, France to Pristina, Kosovo: The cheapest option was to use LifeMiles which are as abundant in the world as Avios. The search was simple: CDG-PRN.
  6. Pristina, Kosovo to Bodrum, Turkey: This is a great example of how having multiple points currencies pay off. Turkish Airlines is part of Star Alliance. Hypothetically, I could book this flight using United miles, LifeMiles or Aeroplan miles. In this case, the best, cheapest option was to transfer Citi ThankYou point to my Turkish Miles & Smiles account. At 11,300 points, this was by far the best way to get to the Turkish Riviera.
  7. Bodrum, Turkey to Bahrain by way of Kuwait City: There is a nonstop flight from Bodrum to Bahrain. Since I needed to add another country to my list (see 126 Countries Left, If I Go), I am taking the scenic route to Bahrain, stopping in Kuwait City for 8 hours. This time, the best deal was on Aeroplan. Instead of paying $2,025, I paid 20k points and $80.
  8. Bahrain to Riyadh, Saudi Arabia: To get to my final stop, Riyadh, I used Aeroplan points once again. 15k points and $91 is far better than $958.
  9. Riyadh, Saudi Arabia to San Juan, Puerto Rico: The best way to find long-haul points flights is to search the longest segment first then tack on the shorter segments. Typically, when I search X to Puerto Rico, I never find availability. Luck was on my side this time as I typed in RUH-SJU and found an impeccable deal of 80k AA miles and $90 on one itinerary (see AA Business Riyadh to San Juan Business: Big Deal, Small Deal, No Deal?).

257,100 points and $1,162.08 versus $26,733. You decide.



  1. Always interesting to see some of the crazy trips you’ve booked. For me personally it’s even more interesting to see how you booked them. One thing that would be immensely helpful for people trying to emulate part of your trips (I’d say it’s kind of unlikely that anyone would duplicate the entire trip) would be if you gave some idea of how far in advance you booked flights, particularly for long haul business/first class flights. For example, I’ve been interested in fly QSuites but can never find space half a year out or less. If you pulled this off then at least I’d know it’s possible.

    • How far in advance did you book the long haul flights? Finding Qsuites space to or from the U.S. in the 1-6 month range has been my personal boogeyman. Any suggestions or insights are appreciated.

  2. AA was the long haul, so that was one week. Iberia was the other, two weeks ago. Qatar I’ve had luck way in advance and last second. But this time I couldn’t find anything to any airport which is, among others, why I settled for AA. (All written in the AA post linked in this article).

  3. I love your writing, your humor, and your stream of consciousness posts which often lead to very strange and unexpected conclusions. This time, however, I think I missed the set-up for “the best itinerary” post — the reason you booked this rather messy (on a map) journey or what you were trying to accomplish. I’ve got the “so I can celebrate my greatness.” Should I expect more?

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