Greece in Mid-October (Weather and Driving)

This whole itinerary involves quite a bit of driving; I would never spend that much time in a car rushing from one site to another. As they say in Greece, "Siga Siga" (Slowly, Slowly).

But since this is your first trip to Greece and you're coming from far away, I imagine it's pointless trying to reason with travelers who have decided to tick off as many "must-see" boxes as possible and see as much as they can in the shortest amount of time.

Anyway, keep in mind that for most of the route you'll be on winding mountain roads. The driving isn't difficult, but you'll rarely exceed 40 mph on average.

It gets dark earlier in October, and the archaeological sites close earlier than in the summer, so it's a good idea to visit them in the morning. I'm mainly wondering why you're staying two nights in Monemvasia? Do you have a particular interest in this place compared to others?

From Monemvasia, I suggest taking the coastal road via Leonidio to reach Nafplio. Unless, of course, you want to get there as quickly as possible and don't like scenic routes. You could just as easily visit Mycenae and Epidaurus from Nafplio.

Regarding days 15 to 19, I'm also wondering why you've planned Mykonos? Are you wealthy partygoers? The main reason why people who know what they're looking for go to Mykonos is this:

https://youtu.be/dMpaksY4sTE

Is there a reason you put the island time at the end?
You need to be in Athens on day 19 to fly out, correct?

I would consider putting all your days in Athens at the end. I would go to the islands first. Then rent a car.

Realize that Mykonos and Santorini are the most touristed and expensive islands. I would consider replacing Mykonos with another island or spend 3 nights on Santorini and move the 2 nights you have for Mykonos to Peloponese. Five nights really isn’t enough time for two islands. You lose 1/2 day moving between islands.

I think you need one more day in Nafplio. Mycenae really isn’t on the way to Nafplio from Montemvasia.

Your day 10 has a lot of driving. You might add a night somewhere before Montemvasia.

We were in Greece from 11th October to 25th October last year.

We didn't drive so can't comment, but weather wise it was pretty good for someone that doesn't enjoy hot weather.

We started in Athens and that was mid-20s, then went to Naxos which was lower 20s. Both were sunny and lovely.

Next was Santorini, where sadly we got the only rain and clouds of the whole trip. Luckily we did still manage on great sunset on our final evening.

We ended with six nights in Rhodes and again, low to mid-20s and bright and sunny.

These temperatures are in celsius of course.

I thought it was the perfect time to travel.

We visited Greece both spring and fall - the weather is great. Driving in Greece is generally easy. Avoid driving in Athens. We've done it and, while slow, was nerve-racking to the navigator. DO NOT believe the Google travel times on roads other than the super hwys/toll roads. The roads are relatively narrow, often windy and sometimes under repair (or should be). Plus you will want to stop frequently for pix, food, etc. I think Santorini is mandatory once in a lifetime - so picturesque. Monemvasia was a good day trip from Gytheion as was the Diros Caves. We stopped at Sparta, Mystras and Corinth on the way from Gytheion to Nafplion. Tiryns is an easy trip from Nafplion; Mycenae and Epidavros are a bit longer drive. If you want to visit an island other than Santorini, Paros is very good but Naxos is the best. Skip the others with your available time. And yes, do the islands earlier and Athens last. Enjoy your trip to friendly Greece.