Athens/Santorini/Naxos??

Actually Athens and jet lag do not go well together, that is why regulars suggest you fly out to your next island ASAP on arrival in Athens. There is something special about waking up next morning on an island.

The big question for you is what time does your transatlantic flight arrive Athens. I suspect the flight from Philadelphia is direct so it arrives around 10:30 am. Unfortunately the next flight to Santorini is too soon for the connection at 11:40. The next flight is at 15:50 which means about a 5 hour wait. That I suspect is the "gruesome" bit. If your flights get in later in the day there are frequent flights to Santorini at 17:15. 19:50 and 21:50. You will need about 2 hours or a bit less to make a connection.

Indeed, even I wouldn't be happy with a 5 hour wait after a transatlantic. There was a recent discussion on Tripadviser where the person weighed the options of staying in Athens for a couple of days a the beginning or put in the wait time and ultimately decided to wait for the 15:50 flight to Santorini. Keeping your 4 nights together at the end of the trip does allow you the time to do that day trip to Delphi ( which by the way is a great site)
Athens http://www.flickr.com/photos/stanbr54/sets/72157632121475515/
Olympia Delphi Meteora https://www.flickr.com/photos/stanbr54/sets/72157645469717811/

There are several ferries a day from Santorini to Naxos. The most stable is the blue star which departs around 15:00 and arrives Naxos two hours later. It is a large conventional ferry. The other alternative would be the Championsjet 1 or 2. We took Championjet1 from Santorini to Naxos last June and arrived at 1:30 which minimized the ferry wait in Santorini and maximized our day on Naxos.
Championjet 1 is a large cat and stable though not as large as Blue Star. You will want to avoid any of the small seajets which can be bouncy. Chances are any of the larger boats already mentioned and your husband will be fine.

Naxos is a perfect companion island for Santorini and meets all of your wants.
Just as an aside my wife gets sea sick as well and we purchased little wrist bands with a hard button that activates a pressure point which really cuts down on sea sickness. Cost was about $8, By the way that was for a Pacific cruise through 4 days of rough water. She has never needed them on the large Greek ferries.

Naxos is a perfect companion island for Santorini and meets all of your wants.
It's only a 2 hour trip and Naxos is certainly worth the effort.

Naxos Town http://www.flickr.com/photos/stanbr54/sets/72157632094558042/
Trip around Naxos http://www.flickr.com/photos/stanbr54/sets/72157634605629689/
Naxos 2016 https://www.flickr.com/photos/stanbr54/albums/72157671589993576

There are about three daily flights from Naxos to Athens. i am the one who personally witnessed a dozen people miss their same day connection flights home when there was a 4 hour delay because of mechanical issues. It doesn't happen very often but when it does its very inconvenient. Thats why we suggest you get back to Athens at least a day before your return flight.
Hope that helped.

Trying to decide to continue to your final destination after landing in Athens is one of most asked about questions on this and many other forums. So much depends on arrival time in Athens, when the flight/ferry is to your final destination is, how much energy do you have left after a cross-Atlantic flight, age, health, etc.

We have always flown to Athens then stayed for a day or two to catch our breath, rest up, see Athens then head for an island or the mainland we decided to see then return to Athens for 1 or 2 days to make sure we have time to make our flight back home.

We have done this many times and have seen everything there is to see in Athens a number of times. Still we love Athens and we always find something new.

Since we have seen everything there is to see and experience in Athens we always check to see if there is a way to by-pass Athens and get to our final destination.

Again, age, health, time, stress and how tired and jet-lagged you are will be the key to deciding to continue on to your destination with/without a stay in Athens.

As far as getting sea sick, the majority of ferrys are large and very stable, even in rough seas. We have never gotten sea sick. We have also taken flights from Athens to islands that have airports.

If you've never taken a ferry and the time to get to an island is reasonable, 4 hours or so, then it's quite an experience. However, if your destination is an island like Santorini then a flight is quicker and really not a whole lot more expensive than a ferry. Remember, time is money when traveling, especially considering getting to/from hotel to ports, airports, wait time, etc.

More than likely you'll fly with Aegean Airlines, a very reliable and highly recommended company. We've flown them many times and have never had any major delays or cancellations. Still, it's possible.

Aegina is a lovely island, often overlooked because it's so close to Athens, but very nice main town and waterfront with a major archeological site right in town, plus one of the best preserved temple in Greece just a short ride away, an abandoned Byzantine Village in the hills, ancient olive groves and lots more.

Naxos is one of our favorite islands and definitely a must with a nice combination of Old & New World Greece.

Lots to consider and think about and with numerous choices of where to go it can be difficult, but also lots of fun doing your research. The more research you do the harder it is to make a decision.

Still, Greece is one of the nicest and best deals of any European Country to visit.

I agree that it's best to fly directly to an island and save Athens for the end of your trip. It's actually not as grueling as you might imagine. My husband and I are around your age and have done it many times ... mostly because it's just so nice to wake up on an island, and spend your first day just enjoying being there. Then, at the end of your trip, you're rested and relaxed and looking forward to busy Athens.

What time does each couple arrive in Athens? If there is not a conveniently timed Santorini flight, perhaps you could change the order of your trip and fly to Naxos first.

And regarding the ferries ... I too can get seasick in rough water but have never had a problem on Greek ferries. There are never any guarantees on weather but we were there last May and the seas were calm on all three of our inter-island ferry trips. I would recommend taking the big Blue Star to minimize any chance of seasickness.

Some thoughts . . .
We are a couple, average age 79, who are also making a trip to Greece in May. I don't know anything about East Coast flights; but we have a flight from SFO, which arrives at ATH around 5:30 p.m. Our plan is to stay overnight at the airport Sofitel. We'll get an early dinner there, shower, sleep, and catch a morning (not too early) plane to our first destination, Rhodes.
One thing I discovered while planning is that the attractions of the islands are somewhat repetitive; i.e., gorgeous beaches, quaint villages, archaeological sites, etc. For that reason I included Santorini as our natural beauty destination and cut Naxos. Our itinerary now includes 23 days, not counting travel from and to the U.S., to be spent on Rhodes, Crete, Santorini, and Athens. The final determination was based on our interests - - we're huge art and history fans - -and ease of travel. We've already secured very inexpensive tickets from Santorini to Athens, and are watching prices for the other connections.
We've been to Athens before, but there are a couple of sights we still want to see. Nothing could induce me to spend the night before departure anywhere but at the city where the airport is located. Therefore we've put Athens at the end.

You might want to consider Napflio as another close-to-Athens destination. It's an a very pleasant town, close to the ruins of ancient Mycenae. We didn't visit Hydra, but that's also close.

You could also consider flying directly to Naxos then boat to Santorini and then end in Athens. I flew into Athens around 10:30 am and then caught the 12:55 flight to Naxos just this past October. Worked very well. Keep in mind that Athens is ~45 minutes away from the airport requiring transport to and from. If using taxi that will add up doing it for two different stays. I also made the daytrip from Naxos to Delos. It is very impressive and very beautiful with the azure blue sea all around and nothing but the ruins on the island. I will say that the boat ride there was very bumpy in early October. It did not bother me but did see other .people getting sick. I am not sure if sometime in October they stop taking the large cats between Naxos and Delos as well as Santorini because for one of the two trips I was told it was the last week they were going and that was either the last week in September or first week of October. I felt well worth it but then I didnt get sick. I used the sea bands Stanbr referred to as well as using ginger chews, also do not sit inside. Seemed like the sick people were all sitting in a protected area of the boat.
Aegina is wonderful with lots to see. It does require a ferry ride of 45-90 minutes. You could take the larger vs the flying dolphin (the 45 minute one)as they can be bumpy.

I also thought about reversing your order and flying to Naxos first. However on that arrival date the only connecting flight to Naxos is at 17:25 that's two hours later than the first Santorini flight. Keep your eyes peeled for additional flights. It is probably too early for Aegean to add flights but as you can see from the previous poster in October this year there was a 12ish flight to Naxos. Thats lots of time to make the connection. That flight is likely to be added sometime in the new year.

Haven't read all the posts here, but I see that Stanbr's first post says if you fly the American Air (formerly USAir) direct flight from Philly, it arrives at 10:30 AM, so you cannot make a connection to a Santorini flight at 11:40.

I have taken that direct flight 9 times now since 2001 -- and every single time (including 2017) this flight has departure time of 4:25pm the day before, and ATH arrival time of 9:10. This flight is NEVER late arriving, because even if it's late departing from Philly. it has TEN hours mostly over water to make it up. You're off the plane at 9:30 and can easily make that 11:40 plane. The farther forward in the economy section you can get seats, saves you 5-10 minutes deplaning but really... no problem.

CONTINUED --- By taking that 11:40 flight, your sequence can easily be Santorini - 2 hr ferry to Naxos - fly back to Athens, As for that 2 hour ferry ... your husband will not even know he is on a ship! This blue star vessel takes 1800 passengers and 250-300 vehicles -- it is HUGE, a smalll ocean liner in size. It is so level, that you can sit in your reserve seat, and y our drink on its tray doesn't even move. The boat has less motion than a Greyhound bus on a highway. YOu can sit out on the capacious rear upper decks too, and look out at the wake of the boat. Finally, May and early June are notable as THE calmest water of the year, much of the time the sea is like glass.

And no, do NOT skip Naxos .... it is a remarkable island, Stanbr has photographs to prove it to you .... so much to see & do (not to mention about 15 miles of golden-sand beaches all in a row). Last Year Trip Advisor issued its list of the TEN BEST Islands in the WORLD to visit. There was only ONE island from the Mediterranean-Aegean ... Not Santorini, Not Capri, Not Rhodes. NAXOS. Already it is attracting many more people ... so go before it changes. You'll thank us.

I had seen posts saying the flight from Philadelphia arrives around 10:30. I bow to Jans experience. If it is 9:30 then you have lots of time to make that next Aegean flight to Santorini. Perfect.

The arrival time is actually 9:10, even better.

I haven't read all the posts either , but I like the idea of 2 days in Athens front and back of your visit . I am a firm believer in being in my departure city at least a full day and night before a return transatlantic flight .

We were on Mykonos this past May ( about mid month) and took the Blue Star feeey to Naxos . Seas were calm , and the ferry is massive and comfortable .

We LOVED Naxos .

We took the Blue Star from Athens to Santorini (stops in Naxos) this past April, spent 3 nights, then took it back to Athens. I get motion sickness but the ferry was so large I didn't even notice we were at sea. We did experience a flight cancellation out of Santorini due to a strike (hence the reason for the second ferry ride) so I would suggest flying from/to Athens and ferrying between the islands. If your flight back to Athens gets cancelled you can catch the ferry back.

OK. This is a lot to digest, but thank you ALL for this information. I am feeling a bit better about this whole trip. We will have to discuss all of this, but I think we will plan to love Greece and go back again and again. I really appreciate these remarks!

Judy