Planning for The Greek Islands: Part Two

Here is Part One of this series

In our last post we mentioned that we wanted to go to the Greek Islands but had no idea what the region had to offer or where to target our short visit in such a vast area. We figured we'd start in the two most popular destinations: Santorini and Mykonos. We figured these islands are popular for a reason and they'd be a good a place as any to start.

We definately wanted to use our American Airlines / Oneworld Alliance miles to get to Greece. We've been hoarding them for quite a long time and have a nice amount banked. Better to use them now before they become even more devalued.

We figured out that we could get to Europe easily enough, but flying to Athens and the Greek Islands is a bit difficult with American and its partners. Many flights to Athens routed through Heathrow - which adds a lot of money to your "free" tickets in fees (England has high airport taxes and British Airway views frequent flier miles as a fee-worthy perk) so that really defeated the purpose of using miles. Air Berlin, a Oneworld partner, seemed to serve most of the Greek Islands, just not everyday, and mainly out of Vienna. On American we can't get to Vienna from Chicago directly. Additionally, not many award tickets were available on Air Berlin, or its partner, to the islands.

We tried working with two different weeks around Memorial Day: starting the trip Memorial Weekend or ending it Memorial Weekend. Dave ended up calling American directly since the website wasn't generating any results for Greece. For the itinerary starting the Memorial Weekend we found a route that took us overnight from Chicago (ORD) to Dusseldorf, Germany (DUS) (ironically the last time we were in ORD Dave made an observartion of the banners all around announcing this newer route), then a reasonable connection to Vienna (VIE), and finally a less-reasonable connection to Santorini (JTR).
Our goal was to get the return flight out of Mykonos (JMK).

That was not working in any way so we will have to make our way back to Santorini to get home. The first agent, whom really tried her best, got us the route of JTR -> VIE, then a 35 minute connection to Frankfort (FRA) where we'd stay over night. Then in the morning go to Dallas (DFW) onto ORD. This was not going to be pleasant.  Four agents later, we had no luck on getting any tickets to the islands on rewards. Dave then went back to the drawing board on the original itinerary and researched options home (since we secured the hard tickets to get we should be able to work the mainland Europe route easier). With a little more work on his own he found flights that almost reversed our original route with a sleepover in Vienna. Phew!

So the flights are secured with lots of miles and a $300 cash outlay.  Not too bad.   Next post, we'll cover the search for lodging.

Here is our next post: lodging