Returning to the mainland from an island on the same day you have a scheduled flight out is risky. If there is a serious delay or mechanical breakdown of a plane or ferry you'll be stuck. Give yourselves at least a day back on the mainland to avoid this potentially expensive complication. Better yet, save your exploration of Athens for the end, at least 2 full days to see the major attractions.

Thanks for your quick response, brotherleelove2004! so in your opinion, even arriving in Athens from Santorini at 8pm-ish and then flying out to Istanbul the next morning or afternoon would be too risky? You're saying to allow a full day in between?

Obviously not brotherleelove2004, but in my opinion, it's a bit risky to take the last flight off a Greek island. If you miss it for any reason, you're stuck until the next day and you'll miss your flight to Istanbul.

All good points. Thanks, Weadles. Sounds like it would be best, although less convenient, to fly to Athens as early as possible the day before our Istanbul flight. I think that's about as soon as we could get there without losing days in Santorini.

Are you spending some time in Athens before you go to Santorini? If not, then I recommend going back the morning before your flight to Istanbul, so you can at least see the Parthenon and a few other important sites.

Those of us who advise on travel in Greece tend to err on the safe side, especially when it concerns return to the mainland by ferry. Flying back to Athens the day before your flight to Istanbul would be the safe thing to do. But I don't see why a connection from the islands would be different from any other airport connection. Flights from Santorini generally continue even when wind stops the ferries. If there is an air traffic controller's strike, it would affect all the flights, including the one to Istanbul.

There is nothing wrong with spending your last night in Athens, but if you really want that night in Santorini then I would go for connecting flights the same day. If you buy the tickets for both flights together, then if you are delayed, the airline would be obliged to get you on the next available flight. Worst case scenario is you will spend an extra night on Santorini. I don't know about you, but I could live with that.

My thoughts exactly, Heimdall! The time in Athens was another dilemma of ours. We'll be flying in from Rome, so we had thought of just spending that night in Athens and having the afternoon to catch a couple major sites. Then fly the next morning to Santorini..Then on the way out fly from Santorini on to Istanbul (with layover of course). We wish we had more time to spend in Athens, but due to work schedules our time is limited. We chose to devote most of it to Santorini, and possibly a night on Follegandros if daily ferries line up in early June.

Or we could do as you suggest and leave Santorini early the morning before our Istanbul flight and see some of Athens then. That would mean we would fly from Rome to Santorini on the way in and just have a layover in Athens...have I confused you yet? My head is spinning with options, so I appreciate all of the advice from the pros!!!

Also, would love to get your thoughts on the "flex" tickets on Olympic and Aegean airlines. We were thinking we'd close our eyes and go for the slightly more expensive fares just to have flexibility if needed. However it seems there's a lot of "fine print". Anyone have experience with these? Is it worth the extra $ to get the flexible fares?

I think your best option would be to fly directly to Santorini from Rome (look for direct flights), then spend as much time as you can in Athens before you fly to Istanbul. Try to squeeze in two consecutive nights in Athens if you can, not to insure you make the connection, but because there is so much to see.

If you need to change planes in Athens on the way from Rome to Santorini, then allow at least two hours for the layover. Since you are already in Schengen you won't have to go through customs or passport control, so even less would probably be enough, especially if your bags are checked through and you have a boarding pass.

Personally when I fly Aegean or Olympic Air I go semi-flex, but I've never had to use the extra advantages of that fare. Probably your best safeguard is to book connecting flights together, putting the onus on the airline if it causes you to miss a connection.

Folegeandros is very nice, but I'm not sure it would be a good idea for only one night, especially on a tight schedule. Plan to be back on Santorini two nights before your flight to Athens if you go there, and don't rely on the catamaran Superjet to get you back.

"Folegandros"

Thank you Heimdall! I think you've helped me make some decisions! Sigh I think we'll fly Rome to Santorini and then do Athens before our flight to Istanbul. Do you know which airlines fly non-stop from Rome to Santorini? I haven't had much luck finding any.

I'm bummed about Folegandros, as it's a dream of mine, but it sounds as if there won't be enough time for it this trip. I don't think we'll have enough time to leave two nights before our flight to Athens, and from what I've read standard ferries from Folegandros to Santorini may not be daily this early in June.

Thanks again to all for your help!

I was thinking of easyJet, but they don't fly Rome-Santorini until July, so that's out. Check Aegean Airlines for connecting flights via Athens. I did a quick check, and there seems to be a five hour layover for the early flight from Rome, and an overnight layover for the later one. Prices vary quite a bit from day to day, but there are good deals on some. I couldn't get the Olympic Air website to work, but that's another possibility.

Thanks again!!! I'm looking into the flight options. What's the general consensus on Aegean vs Olympic. I saw a flight on Olympic that would go out an hour earlier to Santorini once we arrive from Rome. This would cut the layover down from 5 hours to 4 hours. Wondered if it would be worth it to switch airlines for the second flight?

Or if we stick with Aegean for both flights, is a 5 hour layover enough time to venture out quickly to see anything in Athens? Or maybe too risky once we get the bags,etc.