Every 3 years or so, my family goes on a vacation, and while I'm very glad we are able to, we generally go to an all-inclusive in Mexico or Dominican Republic for a week or two, maybe including an excursion out of the resort. This can be a nice vacation, but I think it'd be fun to do something more adventurous. So for our trip in a few years, I want to pitch the idea of Greece to them. My plan is to fly into Athens, stay 2-3 nights and see the top priority sights during our full day(s), and then do 3-4 nights each on two different islands in the Cyclades (one would be Naxos, taking suggestions for the other), followed by one night in Athens before our flight home. With 4 days on each island, we have a day to get to the island, a day to do a fun excursion or activity, a day for an optional hike, and a day dedicated to relaxation. The second island could be only three days, combining the shorter travel day with the hike or excursion.
My selling points are:
Reasons I think they will be hesitant:
Help me build my argument for Greece, or tell me I need to find someone else to go to Greece with and let my family live their comfortable life going to all-inclusives. Any other tips or insights regarding family travel and/or travel to the Cyclades is welcome!