Planning Our Greece Vacation

Oct 14

It was Amy’s idea to go to Greece, and Steve and I were easily persuaded. We were delighted when Danny and Mei agreed to join us!

I’ve planned many family vacations over the years, and this was one of the most challenging. The steps were the same as with any vacation, but Greece presented some complications that were new to me.

Decide when to visit, and for how long. This step was relatively easy. I decided we should visit in the fall, after the busy summer season and before businesses closed down for the winter. (Spring is good, too, but I didn’t want to wait until next year.) Then I consulted Amy on specific dates that she could take time off from work.
Choose which locations to visit, and in what sequence. Greece is famous for its beautiful islands, and I really wanted the family to experience more than one. But which ones? There are 227 inhabited Greek islands! There were many excellent resources, but somehow the abundance of information made the decision harder. ChatGPT did a great job comparing islands, which helped narrow down the list. And I learned that we should spend a minimum of three nights (two full days) in each location.
Determine the best way to transit between locations. When Greek islands are involved, flights or ferries are needed. This late in the year, there were fewer routes available. ChatGPT was less helpful here, with multiple airports/ports and evolving timetables. One thing I’ve learned is to be flexible; sometimes it’s necessary to back up a step and change the itinerary, to reduce the time spent in-transit. That was certainly the case with our Greece trip.
Find the right balance of scheduled activities. We were five adults spanning a wide range of ages (25 to 62). We had early risers and late risers, walkers and riders, and shoppers and non-shoppers. Major archaeological sites in Greece now require timed entry tickets. And with the big time zone changes (7-10 hours), there was jet lag to consider. I decided to keep scheduled activities to a minimum.
Book accommodations, transfers, and tours. This step wasn’t very difficult, but there were plenty of moving parts. I had learned that travel in Greece is often affected by weather and labor strikes. So I made flexible bookings where possible and purchased some travel insurance. I also booked private transfers to/from airports and ports, a more reliable way for five passengers to travel.

Eventually, it all came together! The planning was fun, and I’m very happy with the result. Our itinerary had a variety of accommodations and modes of transportation, and we’d be seeing very different parts of Greece. As with most vacations, I wish we’d had more time. But we had a lot of fun, and I have no regrets.