Snap! I've got time off in July and have booked a 17-night island hopping expedition through the Cyclades and finishing on Crete.
Now I've been to Greece many, many times. If I was going to recommend an island to start with, it would definitely be Crete - it's big enough that it really caters for every kind of tourist. The weather is probably the best in all of Greece (200 miles off the coast of Africa so it does get hot in July-August). Obviously avoid Malia/Hersonissos unless you like to party hard. Agios Nikolaos and Elounda in the east are very nice (fly in to Heraklion) as is Rethymnon and Georgioupolis in the west (fly into Chania) and I've heard Palaiochora is nice on the south west coast (close to Elafonissi beach - check out the photos).
Otherwise there are plenty of other nice islands - Kefalonia, Santorini and Mykonos are all good, though will get busy in peak season (if you can go early July before the schools finish it'll be cheaper and less busy). These are the more expensive islands though. Crete will be somewhat cheaper depending on where you stay. For cheap deals (I know we're contractors so I'm sure this isn't relevant!) you will have to look at places like Corfu, Zante (Zakynthos is the same place, it's shortened to Zante), Rhodes, Lesvos etc. To be honest even these islands will have quieter resorts so don't be put off by the fact that they all have 'party destinations'. The flights will be cheaper and more regular, and once you get to your resort you could be anywhere and it won't be full of drunken youths.
Any other questions I'm happy to help, Greece is my favourite place
Edit: shameless plug but I made a short YouTube video from my trip to Crete last year. If you can overlook the cheesy Greek dance soundtrack it'll give you an idea of what the northern coastline resorts are like: https://www.youtube.com/watch?v=IkiO4T58m0U
Now I've been to Greece many, many times. If I was going to recommend an island to start with, it would definitely be Crete - it's big enough that it really caters for every kind of tourist. The weather is probably the best in all of Greece (200 miles off the coast of Africa so it does get hot in July-August). Obviously avoid Malia/Hersonissos unless you like to party hard. Agios Nikolaos and Elounda in the east are very nice (fly in to Heraklion) as is Rethymnon and Georgioupolis in the west (fly into Chania) and I've heard Palaiochora is nice on the south west coast (close to Elafonissi beach - check out the photos).
Otherwise there are plenty of other nice islands - Kefalonia, Santorini and Mykonos are all good, though will get busy in peak season (if you can go early July before the schools finish it'll be cheaper and less busy). These are the more expensive islands though. Crete will be somewhat cheaper depending on where you stay. For cheap deals (I know we're contractors so I'm sure this isn't relevant!) you will have to look at places like Corfu, Zante (Zakynthos is the same place, it's shortened to Zante), Rhodes, Lesvos etc. To be honest even these islands will have quieter resorts so don't be put off by the fact that they all have 'party destinations'. The flights will be cheaper and more regular, and once you get to your resort you could be anywhere and it won't be full of drunken youths.
Any other questions I'm happy to help, Greece is my favourite place
Edit: shameless plug but I made a short YouTube video from my trip to Crete last year. If you can overlook the cheesy Greek dance soundtrack it'll give you an idea of what the northern coastline resorts are like: https://www.youtube.com/watch?v=IkiO4T58m0U
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