I love to travel in September or October to prolong the summer... This time
the plan is to go to Greece.
Greece has many many beautiful islands

I have been to Greece three times - cycling trip to Corfu (2004), holiday in Creete with a short stop in Athens (2008) and meeting friends on Santorini
and Mykonos (2014). So where to this time?
Santorini

This time I am traveling with my family and none of them has been to
Greece. That is one of the reasons we chose Greece besides the fact that Greece has great food, lots of sunshine and islands, friendly people ... But the deciding factor was that I found really cheap plane tickets from Tallinn to Athens - only 97,72€ per person (hand luggage only).
Mykonos
It is not easy to find direct flights with great prices! The key is to plan early and look out for sales!

So as my travel companions have not been to Greece we must have a look around in Athens and definitely go to Acropolis. We arrive really early in the morning (at 7am) and our check-in is at 1pm, so we have plenty of time to get from the airport to the city, and to enjoy breakfast in some cosy cafe.
Acroplis, Athens
Hopefully, we can sleep on the plane as we take off at 3am, to have enough energy to explore the city. In Athens we will also meet my friend Dimitra, whom I asked for help to decide which islands to visit this time... Have a look at the map and you can see there are so many islands!
Beach on Creete

I had decided that we have enough time for two and Dimitra recommended Sifnos and Milos. So we stay on Sifnos for 4 nights and on Milos for 3 nights. We stay the first night in Athens, and leave to Sifnos next morning. The ferry takes 3 hours and it costs 40€ per person. 

One recommendation when looking for ferry tickets. First Google which companies offer their services on the route, have a look at the prices and then go to the website of the ferry company as it is much cheaper to buy from them directly.
Black sand beach on Santorini