Where: Greece: Santorini, Mykonos, Ios (amongst others)
When: Sometime between Spring and Fall… Nobody wants to be there when its too cold.
Get there: Greece is the perfect place for Island hopping. The ships are quite cheap (unless you chose the speed boats) and the distances if you’re in the Cyclades Islands are small so you can get easily from one place to another. However in most of the islands you’ll find small narrow streets in the cities and villages and they can also be pretty steep. So if you want to get around and see the windmills you’ll have to walk, but its always nice to discover new little streets and shops on the way.
Price: Getting to a Windmill is for free, but most of the times you cannot go inside and they’re locked. Once in a while you’ll find one that is open and you can get in for a donation or a very small fee (I found one in Mykonos).
Do: Why eat always at a restaurant when you can do it outside? Buy stuff for a picnic at a local supermarket, find a place with a nice view and enjoy there. In Greece it is generally accepted to drink outside so you wont get in trouble if you have some beer or wine at your picnic. However please clean everything up when you’re done so the place stays as beautiful as it is (also there is a high risk of fire in the summer when you leave glass bottles outside).
My tip: Travelling on a budget? Don’t book your ship tickets online. In my experience you’ll only find the speed boats which are way more expensive then the normal ones. Every island has at least one travel shop. Just go there and ask them for the cheaper ship tickets and you can save up to 30 Euros.