My fiancé and I are traveling to Greece from the US for our honeymoon at the end of May/beginning of June. After 8 years together, this is our first big trip abroad together. We will be there for 15 days inclusive of travel.
Our tentative itinerary is as follows:
Day 1: ORD —> ATH
Day 2: Land in Athens in the AM. Get coffee/brunch and check into our airbnb.
Day 3: Meteora
Day 4: Visit Acropolis, ATH —> Milos.
Days 5-7: Milos (Plaka, mining museum/Paliorema, Sarakiniko, Paliochori beach, Firiplaka beach, archeological museum
Day 8: Ferry to Naxos
Days 9-12: Naxos (Naxos Town, Agios Georgios/Agios Prokopios/Mikri Vigla beaches, Portara, Mount Zas, Eggares Olive Press Museum, Alyko)
Day 13: Ferry to Santorini
Day 14: Santorini
Day 15: Santorini —> ATH —> ORD
We are in our late 20s and would like a mix of relaxation and exploration. Our interests include beautiful beaches, historic sites and museums, great food (and drink/coffee!), cute towns/cities, and scenic hikes/drives. Clubbing/luxury shopping don't interest us at all, and we prefer to avoid tourist traps unless there is something that is a must-see. We would love to get to know authentic Greece and its people in addition to sight-seeing. Our vision for Santorini at the end of our trip is to get a villa with caldera/sunset views in Oia (or Imerovogli?) to hole up in for the afternoons/sunsets and go into town for some drinks and a bite to eat after the tourists clear out at night.
Primarily, I am looking for advice on the order in which we should visit the three islands. Ideally, we would end in Santorini, but I know that it would be easier to take ferries from Santorini to/from Naxos and Milos than it would be to take a ferry directly between Milos and Naxos, so we are considering going to Santorini in between the other islands. We are thinking of flying directly to our first island from Athens (and then flying back to Athens at the end) as it seems like it might be faster (and I am somewhat worried about getting seasick, so this would eliminate a few extra ferry rides). We only plan on spending two or so days in Santorini because of how touristy we have heard it to be, and will spend the bulk of our trip on Naxos and Milos.
Overall, we are trying to be somewhat frugal, with a few splurges throughout the trip (such as our hotel in Santorini).
Other questions: is Meteora worth giving up a full day in Athens? Should we prioritize a boat ride out to Kleftiko or Cave of Sykia in Milos? Are there any other boat rides/snorkeling excursions you'd recommend? In addition, we would appreciate any suggestions for places to stay, food/coffee, and sights/activities!