What are the pros and cons that some of you have found with booking in advance vs. booking while we are in Greece as we go?
I am concerned that room prices will be steeper, and we will not be able to find availability.
Chania June 8-12
Santorini June 12-14
Naxos June 14-16
Mykanos June 16-19
Athens June 19-23
Definately book before arriving in Greece. Hotels are fully booked in Greece and specially on islands.
You should book earlier or decide on some other destinations other than Santorini & Mykonos.
Since Chania on Crete & Naxos are large enough to offer more options and escape from tourists you should be OK but may want to pick other islands beside Santorini/Mykonos
However, if you have your heart set on the Big Name Islands book ahead of time and prepare to spend lavishly.
Athens is Athens. Regardless of when you go they'll be people. It's a city of millions but you'll have a lot more options for accommodations in a wide variety of prices and you can find places out of the tourist zone to escape the crowds.
We had trouble booking hotels in Greece four months ahead and had to reverse our itinerary to get reservations. Book ahead now.