About my credentials to advise, Travelsoon, it is from deep study and long experience. I wanted to go to Greece since your daughter's age but Life got in the way... couldn't go until my 60s but since '99 I have made 12 trips of 3-4 weeks each -- on 9 of these I took along 3-4 "travel pals" so I could afford it (I'd do the planning & organizing, they pitched in to cover my airfare).I have visited 25+ islands, many of them multiple times (Milos 3x, santorini 7 times, naxos 13x, Paros-antiparos 6x, Crete 7x, and many East Aegean islands as well), a dozen major sites on mainland. I have 2 shelves of Greek travel guides, 3 shelves of other greek titles, have taken grad. course in Greek lit, archeology etc at U. of Penn. I have numerous Greek friends I now visit with on each trip, and contact constantly w. them and other frequent Greece travelers to stay current. So yes, I am experienced.
I don't want to sound scoldy but I will -- PLEASE just look at a MAP. in your eagerness to avoid a stop in Athens, you are setting yourself up for a Back-track. Why? By trying to start w. Santorini. You never mentioned wanting to visit Santorini (in fact you listed it among islands you'd already visited). Second, if you look at a map you'll see that there are several Cyclades Island chains http://www.explorecrete.com/crete-maps/images/greece.gif (click & it gets BIG) -- West, Central and East -- and they almost never connect. THis (outdated but useful) ferry chart shows that Santorini is the CONNECTOR between west & central. http://www.greeceathensaegeaninfo.com/ferry-info-greece/greek-islands-ferry-chart.htm Therefore, if you want to include MILOS, Santorini needs to be in the middle, not first. That is why I gave you the sequence before. I know this from experience.
Besides, what is the problem about stopping in Athens airport? You don't have to go near the city itself. You land, carry your luggage to the other end of the airport, and get on a domestic fiight to Milos. Allow 90 mins, just in case your Europe flight is delayed a bit. Done! After time on Milos -- daily ferry goes to Santorini. i recommend no more than 3 nights there, then leave on 10:30 am fast-ferry to Naxos, for at LEAST 4 nights, then on to Antiparos. From Paros you can fly.. OR ferry back (7pm - 11:30pm) 1 day in Athens for the Acropolis then FLY. OR... you could do reverse -- start by flying from ATH airport to paros, it's a 10-min. ferry to Antiparos - then Naxos- Santorini - Milos - Fly direct to airport & gone!
As for Santorini, you haven't been there since the Monster Cruise Ships have made Oia look like Times-Square rush hour between 10 am - 4 pm. Of course, it's lovely, but I advise taking bus tosee it between 8:30 - 10:30 am, then scramming. when 3-4 Megaships dock daily, that's as much as 10,000 cruisers, PLUS all the bus-tour mobs. I have found away to enjoy the Famous View, from a lovely balcony on Caldera, where NO group-tours go... stay in Firostephani. That's an area just NORTH edge of Fira, walkable to shops, museum, cafes (and some really nice cafes of its own) but no crowds. Lovely hotels right on the rim path, and from their inland side, just steps to bus stop. Of course, you're very late making plans --remember June is Bridezilla month, and Santorini is destination #1!! You may need to rely on a savvy Greece-based agency to get you a booking -- 3 well-regarded ones (Dolphin-Hellas, Fantasy Travel, Aegean Thesaurus) are used to working via E-mail w. N. american travelers.
If you still want to do it yourself, the key is -- get logistics locked in first, before you do hotels. You need to use both the ferry schedule website -- http://www.gtp.gr/RoutesForm.asp -- and the flight websites. The Aegean site is good --http://en.aegeanair.com/e-services/e-ticket/ and also one that shows Ryan air & a few others -- http://www.airtickets.gr/flights.asp?lang=en This will take time and patience ... of course this is melting your brain. You can't short-cut it unless you use an agency. But sometimes when you don't have the time to spend, you must spend the money; it's a trade-off.
Next, hotels. If websites show 2 rate levels, one nonrefundable, and another slilghtly higher that's changeable up until 2 weeks before -- don't lowball it. you may regret it. One quick way to see both availability and location is to use Booking.com AFTER you have have figured what dates for each place. Put in location (Firostephani Santorini), and click on the first hotel, just to bring up the Google MAP, which shows the LOCATION of all the available hotels, RED circles for fully-booked, blue for still available. (NOTE: some hotels shown as fully booked still hold back a few rooms ... not always the ones with the best balcony views however).
