Greece in October

We travel to Greece in October every year because it's the off-season with lower prices, less tourists and still very nice weather. What are you looking for in a Greek experience: islands, mainland, culture, nightlife, partying, shopping, archeological interests, beaches, etc? There are many choices of where to go in Greece. What we do is fly to Athens and spend a couple days catching our breath and visiting our favorite areas: Acropolis, Plaka, Anafiotika, Central Markets, various squares and archeological sites & museums. We usually take a ferry or fly to an island and spend most of our time there then return to Athens at least one day before our departure. Normally weather is still very comfortable with usually just a short sleeve shirt during the day and even at night. More chance of rain but not a real problem. You need to be more specific in what you want from your time in Greece.

I have enjoyed Greek islands in the first two weeks of October, including some of the smallest, e.g., Agathonisi and Lipsi in the Dodecanese. I swam in warm, protected harbors on those two islands and also spent a beach day on Patmos. This trip was by ferry and finding accommodations upon arrival. Expect ferry service to be about half what it may be in high season and island buses also sparse. Weather, hotel and restaurant accommodations quite adequate.

I also had mostly fine weather (with some rain) and accessibility in late October on the northern Greek mainland, around Thessaloniki, Larissa, and Meteora. But found the resort-y Halkidiki peninsula quite dead by October 30 (like I was the only tourist). This trip was with a rental car and driving no problem (except for rocks on mountain roads and resulting flat tire).

For your first trip, I'd actually focus on the Peloponnese area covered in Rick's guidebook, together with Athens.

We went w/ our college age boys a few years ago, in December. We're from Minnesota. To us it was warm and our sons wore shorts in Athens. They had many stares.
In December we covered as far north and inland as Meteora and were not "cold" except for one day at Mycenae where the wind whipped off of the sea. THAT was MN cold. but I wouldn't have packed differently, we survived the ONE day, ONE location.