We are just fine-tuning our early July plans and have, so far, come up eith the following options :

Option 1 :
Day 1: arrive Athensand immediately fly/ferry to Chania, Crete
Day 7: ferry to Santorini (arrive before noon)
Day 10: 7:00 pm ferry to Naxos
Day 13: 5:45pm ferry to Piraeus
Day 14 : 12:00 noon flight to Florence
Day 15 : Malls/Montepulciano
Day 16 : Pienza/Chianti
Days 17-21 : Cinque Terre/ Rapallo
Day 22: Florence
Day 23 : depart for Toronto

Option 2:
Day 1: Arrive Athens and immediately ferry/fly to Chania
Day 8: arrive Santorini by noon
Days 9-11-Santorini
Day 12 - fly Santorini to Athens (early morning) and fly to Florence at noon
Day 13 : Montepulciano/Pienza
Day 14 : Chianti
Day 15 : Malls/Lucca
Days 16-21 : CT/Rapallo
Day 22: Florence
Day 23 : Toronto

Please note that Florence and Athens are absolutely no priority - we spent a day in Athens 2 years ago and have no desire to return for any period of time, and we have been in Florence twice in the last 2 years, and have seen all the sites- we feel that a nice leisurely evening when we arrive as well as a relaxed day there before leaving (with of course 2 wonderful dinners being fitted in) will be more than acceptable.

Any comments?

Top-up for the afternoon crowd.

Commenting just about the Greek segment, looks fine to me ... only query, you're obviously taking the fast ferry from Heraklion-Thira (Flying Cat 4) .. if that date is a Wednesday be sure to check Hellenic Seaways site because it doesn't run on some specific Wednesdays; I discovered that and had to rejigger my itinerary.

Traveljan - thank you for your response.

There is no questionable Wednesday involved.

However, when you say that the Greek segment looks fine, which one do you mean? The longer Crete-Santorini-longer Italy one or the Naxos-Santorini-shortened Crete/shortened Italy one?

Thanks again.

I just wanted to make sure that you realized that the ferries for Santorini only depart from Heraklion, which is a two-three hour drive from Chania.

Weadles - our plan is to rent a car for our last 3 days, and will either drive to Heraklion the day before to visit Knossos (after some time at the beach), and stay near the port for the next morning boat, or (less likely) we will wake up very early on our last morning and drive to the port at Heraklion to drop off the car and board the ship.

Any more comments or suggestions?

Thanks for any advice.

Nevertoold i would suggest you to fly directly from the airport to Chania. Don't even go to athens, and there's no point going by ferry since aegean airlines have some great prices for Crete. (If you only put the taxi cost to Piraeus & ferry tickets flying may even be cheaper as long as you book them early).
I can't advise you about skipping or not Naxos but there are a lot of people in this forum that like that island very much, so consider the option1 carefully.
One more suggestion for Santorini.. Stay in Oia! Have a great time! ;-)

cristine - thanks for your advice, but we arrive in Athens at around 11:30 am, and the next flight out is too close in time to leave ourselves room if our flight from Toronto or our Paris connection is delayed.

The alternatives appear to be a late afternoon high-speed ferry, which we should be able to easily make, or an afternoon in Athens (to see the Parthenon/acropolis again), and a late-evening flight.

Unfortunately, unless somebody can assure us that a 12:00 noon arrival into Athens airport on Air France flight from Paris combined with a 1:30 departure to Chania is feasible, an "in and out" airport situation does not appear to be a viable alternative.

I see that aegean has flights for Chania at 16.00 as well. Check that out in their website.
Otherwise i would suggest you to stay that day in Athens and see Parthenon, go to Plaka for dinner etc, and leave the next morning for Chania.
Where have you seen late night flights for Chania? On olympic airways?

cristine - you are correct.

Aegean must have recently instituted a 4:00pm flight, as I did not see it nthere last week.

The other flight is Aegean at 9:10pm and is also on the web-site.

Thanks for your info.