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Itinerary Three Weeks Greece Fall 2018

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I need help on deciding places and times for a three week trip to Greece in the fall of 2018.

My wife and I are in our mid to late 60"s and like history, nice local towns, mid-luxury accommodations, good local food and normally stay at high end rental apartments or boutique inns and hotels.

We are leaving the US on September 25, 2018 and arriving in Athens on the morning of the 26th.
This is what i have so far, please advise on how to modify.

9/26/18 -USA - Athens
9/26/18 - Athens
Rental car
Lodging Nafplion 4 nights - Adiandi Hotel
Multiple day trips
Day trip to Spetses
Travel to Monemvasis - 2 Nights - Byzantino Boutique Hotel
Lodging Kinsterna Hotel & Resort - 3 Nights
Multiple day trips and relaxing (cooking classes, massage, chill)
Return car to Athens airport and fly to Santorini
Pick up rental car
Lodging - 3 Nights - Rental Apartment Oia
Return Car
Ferry to Naxos- High Speed
Lodging Naxos - Either rental apartment or Kavos-Naxos Hotel - 4 Nights
Return car
Ferry - Blue Star to Athens (Piraeus)
Lodging- Athens Rental Apartment - Plaka- 4 Nights
Fly out Athens to USA

Please advise on how I should modify my trip and if any of my predetermined lodgings should be switched.

Thank you in advance for your assistance.

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