Absolutely no problems - have only ever slept at an airport once (out of choice - didn't think it was worth paying for a room for 3 hours!) and sat on a beach waiting for a village to wake up once! This is in 16 years of DIY to Greece.
Personally I would go for Late September (depending on where you're headed) - nice and quiet (but room prices don't really plummet until October) - the sea's nice and warm.
If you want deatiled info - drop me a personal message!
Personally I would go for Late September (depending on where you're headed) - nice and quiet (but room prices don't really plummet until October) - the sea's nice and warm.
If you want deatiled info - drop me a personal message!
I have been going Greek island hopping for something over 2 decades, never booking accomodation in advance. It is very easy to get accomodation on arrival out of the hi-season (July-August).
This applies to every standard of accomodatiom, however on the smaller islands there just is not any 3-5 star at all, it is either a small hotel 1 star or 'rooms for rent' places.
The times you suggest yourself are perfectly OK times to go.
Easy islands groups to start with would be the Cyclades, Sporades(ex Skyros), Dodecanese. You can fly direct to one of the islands within the group of islands or of course start in Athens.
This applies to every standard of accomodatiom, however on the smaller islands there just is not any 3-5 star at all, it is either a small hotel 1 star or 'rooms for rent' places.
The times you suggest yourself are perfectly OK times to go.
Easy islands groups to start with would be the Cyclades, Sporades(ex Skyros), Dodecanese. You can fly direct to one of the islands within the group of islands or of course start in Athens.
As the previous replies as have suggested it is very easy especially in September/October. We are in our 50s and have island hopped for longer than I care to remember.
There is no stigma attached to having a look at any rooms offered and then politely declining to find somehwre else.
If you arrive somehwere late just take a room for one night then look for another the next day. Most Islands have a small tourist room office and even those that don't, just ask at the ferry ticket office.
Go for it and have a lovely time.
There is no stigma attached to having a look at any rooms offered and then politely declining to find somehwre else.
If you arrive somehwere late just take a room for one night then look for another the next day. Most Islands have a small tourist room office and even those that don't, just ask at the ferry ticket office.
Go for it and have a lovely time.
Dave, I really envy you! We are both around the 60 mark, I want to try island hopping, but Mrs Parky won't wear it. 
For a first time, my start would be from Rhodes where you have a choice of Tilos, Kos and Symi. They are all a short hop from Rhodes. You'll get plenty of choice of accomodation in those places at both times of the year.
Good luck anyway.
Parky
For a first time, my start would be from Rhodes where you have a choice of Tilos, Kos and Symi. They are all a short hop from Rhodes. You'll get plenty of choice of accomodation in those places at both times of the year.
Good luck anyway.
Parky
been island hopping for years now. may/june is a nice time to go as its still low season so rooms will be cheaper. you will easily find accomadation when you arrive at a port. i think the cyclades is a good route to take.
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