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Feedback Requested on 2 wk Naxos-Santorini-Athens Itinerary for Family of 4

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I would appreciate some feedback on a tentative itinerary that I put together for our Greece vacation. My husband and I are planning a trip for two weeks next June/July 2016. Our two sons, who will be 11 and 13 years old next summer, will be with us. This will be our first time in Greece.

A little about ourselves: When we are on vacation, we like to relax, take our time at different sights, have leisurely-paced meals with high-quality, healthful foods (all 4 of us are foodies!), and over the years have realized that we enjoy accommodations in areas that are less touristy or crowded. We prefer smaller hotels, instead of big resorts. My sons and I are very much into history, so we are planning to view some of the ancient sites. I love architecture. I could also see myself spending hours just staring out to the caldera on Santorini, taking in all the colors and breathtaking views. My husband would really like to stay right on a beach for at least part of our vacation. Our family is adventurous, and we like to stay active on vacations by exploring, hiking, beach activities, but we must also have our downtime to read and lounge. We hope to experience a taste of Greek culture. When searching for an "authentic" restaurant, we would look for where the locals go and not a tourist hotspot. We only have 2 weeks, but we would still like to immerse ourselves into Greek culture, beauty, history, food, and traditions as much as possible - and do this at a relaxed pace, where we return to the US feeling refreshed and grateful that we were able to spend quality time together as a family; we dislike the feeling of needing to take a vacation from our vacation. :)

Tentative Itinerary
14 nights total
Naxos - 5 nights
Santorini - 5 nights
Athens - 4 nights

Day 1: Travel from US to Athens and fly straight to Naxos; Naxos (5 nights, 4 full days); Stay at
Medusa Resort & Spa on Plaka beach
Day 2: Naxos - beach day and explore Naxos town
Day 3: Naxos - Naxos bus tour to explore island; olive and cheese tastings??; check out marble
quarry??
Day 4: Naxos - Mount Zeus hike
Day 5: Naxos - beach
Day 6: Travel to Santorini via ferry; Santorini (5 nights, 4 full days); stay at Athermi Suites hotel in
Megalochori
Day 7: Santorini - Drive/bus to Fira and hike to Oia; watch sunset at Oia (realize lots of crowds)
Day 8: Santorini - Drive around island and explore Megalochori
Day 9: Santorini - Day trip to Nea Kameni volcano and Therassia
Day 10: Santorini - beach/pool day; soak in Caldera views
Day 11: Fly to Athens (4 nights, 3 full days); stay in Koukaki neighborhood at Herodion Hotel
Day 12: Athens - Acropolis; Acropolis Museum
Day 13: Athens - Food focus thru Monastiraki Square and the central city market, Varvakios
Agora; Benaki Museum?? (free on Thursdays)
Day 14: Athens - National Archeological Museum; Syntagma Square; lounge at hotel
Day 15: Travel back to USA

Questions:
1. Given my family description, does this itinerary make sense?
2. How far advance should I book flights and hotels?
3. Are Megalochori and Plaka too out of the way?
4. Should I rent a car on Santorini and/or Naxos, given where we are staying on the islands?
5. What two museums in Athens would you recommend? We plan to visit the Acropolis Museum, especially since it's 2 minutes from our planned hotel. Are both Benaki and National Archeological Museum recommended? I'm concerned that my boys (really, my husband) may be a little "museum-ed out", even though they could spend several hours easily at any one museum. Or should we plan on both Benaki and National Archeological museum and perhaps spend less time at each?

Would love feedback from experienced travelers to Greece! Thank you!

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