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  • Lawrie Wallace

Gypsy adventures and travel

Updated: Oct 3, 2020

Traveling around the world or around town, follow Lawrie and friends on their adventures discovering new places and learn to plan and budget your own dream vacations.





Planning our Greek Island Vacation part 1


Booking an island hopping vacation to Greece within a year of buying our first new home seemed a bit excessive and unrealistic. Which is why it was perfect, you only turn 40 once, go big or go home… this lady is going to the Mediterranean.

Planning big trips is something I am actually quite gifted at. I can break down long hauls into measurable jumps, with maximum comfort for the money spent. I decided a long time ago that a gift like that is best when used frequently.

The original plan was to fly round trip to Athens, Greece and jump between as many islands as we could comfortably afford with a 2-5 day stop at each destination. I imagined us sailing on yachts through the Aegean Sea and wandering through white washed villages in Santorini. There were a few must see spots, but I was fixated on the beaches and scenery we would find. There were so many majestic sites in Greece, and they are not very close together.

We decide to be gone for 21 days. 3 weeks seemed an adequate amount of time to wander and get in touch with what being a Greek beach bum was all about. A trip this long would be an indulgent introduction to my 4th decade on the planet.

The key to this trip was to spend as little money as possible on flights to and from Athens. This would leave funds available for car rentals and ferries between islands. It would also allow us a bit more budget for accommodations.

I had spent countless hours planning routes we could take to see the major priorities of the trip: Santorini for all the classic Greek holiday feels and Kleftiko, which is closest to the island Milos. I also really wanted to see the spot where they filmed Mama Mia, but it was way off the beaten path and would have taken a lot of travel time to get there. Mykonos also came up, but ultimately we were less interested in night life and more interested in beautiful beaches and adventures.

We were planning to travel in late June and early July of 2018. Based on our must see stops it seemed to make more sense to fly to Heraklion, Crete which had an international airport. The we could take ferries between islands, gradually headed North to Athens where we could catch a flight home.

It was the morning of January 17th, 2018 and I knew that if I did not get a move on booking some flights and hotels then it would be harder to get where we needed to be, when we needed to be there.

The first step was booking the long haul flights out of DFW to London Heathrow to Crete all one way. This was also the first obstacle to overcome, because sadly there were no miles eligible flights to Crete from London. I explored other options for how to get to Crete and none of them were fitting into my minimal budget spent of airline flights game plan. What I did find was that Milan, Italy cost a minimal amount of miles to get to and was also a short 2 hour flight to Crete.

We had never been to Italy, and we could have just used it as a connection and gotten to Crete right away… but what’s the fun in that? This was a bucket list trip packed full of new places, and if we were going to stop in Italy we might as well enjoy a bit of it, right? I knew there was so much to see, and I didn’t want to try and cram something as massive as Rome or Venice into just a few days, so I opted for a quick train ride out of Milan to Lake Como.


Lake Como seemed like the kind of romantic getaway that would be fun to see over just 2-3 days and then we could leave the other Italian experiences for another trip. So just like that I booked us a one way flight from DFW to Milan connecting in London and a one way home from Athens connecting in London to Austin to DFW.

The total for our roundtrips flights to and from Greece cost us 210,000 miles + $794.00 in taxes and fees, we also paid for $210 for our flights to Crete from Milan… and we nearly crashed and died, but that’s another story.




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