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Critique a draft itinerary please!

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Hi
Thanks for providing such a wealth of information and a great forum for sharing your experience and knowledge. I’ve read through some posts and have found some great information.
My girlfriend and I plan to travel to Greece, Italy, France and Spain next May/June. We have a comfortable budget and around 4 weeks to cover our itinerary. We have put together a bit of a mind dump of an itinerary which I suspect has way too many destinations. Using the itinerary FAQ’s ‘divide by 3.5’ rule of thumb we should only be visiting around 8-9 places over the 30 odd days we have available.
The current draft itinerary has 25! Haha ☺
I have been to France, but when I was 10 so i don't remember a great deal.
My girlfriend has been to France, Italy and Spain, but on a quick two week Contiki tour.

I'm keen on visiting the Loire Valley and Meteora (please let me know if its worth it).

She is set on visiting Santorini.

To help with responses: the type of advice we'd cherish is advice on whether certain places are worth seeing based on certain attractions (e.g restaurant, landmark, view, festival, nightlife etc), your experiences there, how the place fits in with the others on the list (eg is it not worth seeing place x because place y has a better something anyway) or other consideration. We know we have way too many places and your insight will help with whittling the list down!

Not that keen on:
mosh pit type crowds
nightclubbing/partying
backpacking type travel
museum overload
overrated anti-climatic cliched experiences
touristy booze/drug culture areas/'attractions'
harassment by peddlers

Interested in:
anything to do with food or cooking
meeting people
village life
military history
clothes/fashion
oddball history
essential landmarks
amazing panoramas
One question is whether to fly to Athens and start from Greece, or fly into Lisbon and start from there or vice versa… or something completely different.
Any comments would be great, we'd love if you could share your experiences and help us hack down the number of places we have on the list!
Thanks in advance
Sorry for the long link, but here is our itinerary on Google Maps:
https://maps.google.com.au/maps?saddr=Athens,+Kentrikos+Tomeas+Athinon,+Greece&daddr=Santorini,+Greece+to:Mykonos,+Mikonos,+Greece+to:Delphi,+Fokida,+Greece+to:Meteora,+Ikonomou,+Kalabaka,+Trikala,+Greece+to:Positano,+Salerno,+Italy+to:Rome,+Italy+to:Florence,+Italy+to:Cinque+Terre,+Riomaggiore,+SP,+Italy+to:Venice,+Italy+to:Milan,+Italy+to:Genoa,+Italy+to:Nice,+France+to:Paris+to:Versailles,+France+to:Chambord,+France+to:Mont+Saint-Michel,+Le+Mont-Saint-Michel,+France+to:Bordeaux,+France+to:San+Sebastian,+Spain+to:Barcelona,+Spain+to:Madrid,+Spain+to:Toledo,+Spain+to:Andalusia,+Spain+to:Seville,+Spain+to:Lisbon+Portela+Airport,+Alameda+Comunidades+Portuguesas,+Lisbon,+Portugal&hl=en&ll=42.617791,8.173828&spn=27.915834,67.631836&sll=41.873634,8.197401&sspn=28.235736,67.631836&geocode=FeOVQwIdnhRqASnxQ3AGH72hFDHdjWZ2RTU2Jw%3BFYisKwIdfxGEASnpvOMFzs2ZFDHboe-7ksH0CQ%3BFeJkOwIdLLSCASlFLDBY0LiiFDGAx7niLL0ABA%3BFb1CTAIdloNVASl1Sa6sbXlfEzF93f1IAZ!%205i0Q%3BFd7fXQIdoPJJASFBtL20eTJ7sSnfc-8wzA9ZEzFBtL20eTJ7sQ%3BFVXvawId9QXdACkb0hCnaJc7EzEx3s5jKAvejA%3BFTQ8fwId2He-ACm7jpL5lmEvEzE4bmWTBncPuQ%3BFZnkmwIdgaGrACmt1tKAplYqEzEDKsfvF3nVkw%3BFenloAIdDZWUACkHi6xxifrUEjGAZfiHtA-eEQ%3BFU9ftQIde-u7ACmJPdbx2rF-RzEvEJK98Majew%3BFW6_tQId1CyMACnndRI_ScGGRzGNDnTGE83_PA%3BFZKTpQIdUIKIACmtmtTcUkHTEjEKYoEY8YRqIw%3BFaS_mgIdON1uACkxLYVqENDNEjFwmpf9pRkIBA%3BFSZ-6QIdXuQjACkPt-IGH27mRzFglIxow4ILBA%3BFXCz6AIdNmAgACGPzllfwfw4BSl1TLHXlH3mRzGPzllfwfw4BQ%3BFTeQ1gIdpiYXACFxKA5hdbAfbSkhKLh-063kRzFxKA5hdbAfbQ%3BFZIf5gId2_Do_yGWn9h5IiU7OynBxww3RFgGSDGWn9h5IiU7Ow%3BFZ0rrAIdlCn3_ymBylH36CdVDTGJejl7A4ZjeQ%3BFT78lAId0cTh_ykV_mg7_q9RDTFJRoaUWcU-5A%3BFWh8dwId3CkhACnlMI5xFpikEjEKZkdPPfuwRA%3BFQe2aAIdEnzH_ymBPAqAlylCDTFpIoxhwd42xA%3BFTBCYAIdRYzC_ynx_bULrQtqDTH-rXVq6Ft_xg%3BFU_hPAIdN9y3_ylFxZ3PsdkRDTEP8_F3TWXJwQ%3BFUB_OgIdhrek_ymRYr4UEWwSDTFIVv4cYhjwNA%3BFf6WTwId0LF0_yFGbQNYPqVmCimDAdkWRjIZDTFGbQNYPqVmCg&oq=Athens,+Kentrikos+Tomeas+Athinon,+Greece&t=h&mr!%20a=ls&z=5

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