Greece Plus Santorini and Mykonos with NO boats?
 

This will be a first time travel to Greece for my husband and I in early September. We have an 8-Day Trafalgar Tour of Athens, Olympia, Delphi, Meteora in mind for mainland Greece. In addition we'd also like to see both Mykonos and Santorini however my husband has gotten seasick in the past so ferries are out.
1st question is is it feasible or crazy to consider flying from Newark to Athens and then immediately flying on to Mykonos for 2 nights, then fly back to Athens to take our land tour which starts and ends in Athens, then flying to Santorini for a few nights before returning to Athens for our flight back to Newark, NJ?
2nd -- how many days should we leave per each island?
3rd -- what part of the island of Santorini for hotel that's well situated for getting around and seeing the island w/out a car (Fira, Imerovigil, Oil, Firostefani)?
4th -- what suggestions for sightseeing on each island?
We're both 70, in pretty decent shape so looking for a moderate activity trip. Not sunbathers but like seaside villages.
Thanks in advance for suggestions and insights.

I think your plan to fly to each island is fine. It is nice to go by ferry with fresh air and seaviews but I totally understand if your husband wants to avoid boats. I get motion sickness on just about anything that moves. He could try different drugs for motion sickness, I've only found two types that work for me in all the years I've travelled.

Three nights would be the minimum amount of time I'd want on each island, longer if you can. On Santorini there are buses and taxis to get around. We stayed in Fira and Oia and preferred Oia.

Spending the night before your international flight home in Athens is sensible but that does mean an extra one night stop.

If you're self connecting what are you going to do if your first flight is late or if either flight gets a schedule change?

You can certainly fly but you're looking at losing a chunk of time. Not saying you won't lose time with the ferry but if you only have two days spending most of one arriving and most of a second departing I'd question if it's worth it.

You plans sound very rushed. I think Greece is best enjoyed at a more leisurely pace and being frequently at the airport and on planes wouldn’t be what I would choose.

Thanks KayF!

Good point...May need to build in extra days if I'm doing those flights

Thanks Traveler_Nick. I've read on Fodors and Rick Steves pages suggesting an immediate flight to an island after landing in Athens. I have thought about the long travel day with a 9 hour flight followed by collecting luggage and getting on another flight. Might work better for travelers from Europe to Athens which would have a shorter flight time.

Why not choose one of the islands, spend longer there and relax a bit? I understand the desire to see it all, but sometimes, most times, less is more. Cuts out two polluting flights too. Given Rick Steves and Fodors cater for American travellers why not take their advice, bite the bullet with one long travel day, a few days on one island then back for your tour, and fly home after the tour?
Both those islands are over touristed even in September.

If you do a flight Newark to Santorini (instead of to Athens and then a separate flight to Santorini), your luggage will be checked through to Santorini and you won't have to pick it up in Athens (or elsewhere if your connection is somewhere else). In addition, if it's all on one ticket to Santorini, if your original flight out of Newark is delayed and you miss the connection, they have to put you on the next flight to Santorini. If Athens to Santorini is on a separate ticket and you miss the connection, you will have to buy a new ticket.

Same thing on the way home from Mykonos, do it all on one ticket. You would search for a multi-city ticket, Newark to Santorini and Mykonos to Newark.
Or vice versa if you go to Mykonos first.

My thought, too, and and an obvious way to reduce stress & the chances of a hang-up that airlines seem so ready to inflict on us. Being there is the joy of travel for most of us, not the moves from one place to another. With 4 or 5 nights somewhere you can begin to relax into the experience that Greece is & you’ll be ready for your tour. I think on such a short trip so far from home you’ll love the longer stop with a deeper dive into one place.

Of course if you do just one island (a good idea with your time), the multi-city ticket would be Newark to Santorini and Athens to Newark. You could add Santorini to Athens in the middle, but I don't know if that will be more expensive than doing just Santorini to Athens.

Thanks SusanP. I assumed the flights to Santorini were little puddle jumpers that we’d have to ticket separately. I’ll look into making it one flight ticket and maybe limit to just one island as. Few folks have suggested.

If you book with the same airlines, like Aegean Airlines, which is the most reliable in Greece, you will not have to collect your bags. Please note that Aegean Airlines is star alliance, so if your other flights are combined with the same group that would not be the issue.

Travel to the Greek islands generally takes more effort coming from North America. It once took us 28 hours SFO-MUC-ATH- CHQ. We are currently in Rhodes but arrived directly from London after a week in the Cotswolds. So much simpler than several flights all at once. I too get sea sick so also rarely do ferries. I think flying on one ticket EWR to either JTR or JMK should be on one ticket or cover yourself with travel insurance. Given your time limits I also would just do one island.

Thanks!