Naxos, Paros or another island, and Santorini- Itinerary advice

You don't have enought time for 3 islands and Athens if you want a relaxing holiday. Choose Paros OR Naxos. They're similar enough that either will be a good fit with Santorini.

Each island hop eats up a minimum of a half day. The less hops you take the longer you have to enjoy the two Islands you choose.

Purely on a logistical point of view all three islands have airports. Santorini is a busy international airport with lots of flights. Paros is much smaller but does have more daily flights than Naxos. Naxios airport is very small. Choosing your islands may be influenced on the timing of the flights. You need two hours after landing in Athens to make a connection. Once you determine the best connection you will know which island makes the most sense. If you are arriving in the early evening there there will be no more flights to Naxos. The last flight to Paros is at 6:15. Santorini will have flights even in the late evening.
If you can make a Naxos connection then I would suggest that St George beach which is part of Naxos town perfectly suits your wants.
Naxos Town http://www.flickr.com/photos/stanbr54/sets/72157632094558042/
Trip around Naxos http://www.flickr.com/photos/stanbr54/sets/72157634605629689/
Naxos sunsets https://www.flickr.com/photos/stanbr54/albums/72157700728046481

Becky, plan your flight logistics before you book your hotels (and BTW, in hotels don't go for the rock-bottom nonrefundable rate; the risk is not worth the minor savings). You might also consider flipping your sequence depending upon WHEN your flight from US arrives in ATH. this is a price/time decision; here's the deal.

Only 3 nonstops (priciest) from N. America -- from PHL, JFK or Montreal -- arrive between 9 - 10:30 AM, giving you the most choices of onward flights.... If you opt for cheaper fare, you change in Europe and may not arrive until 2-5 pm NAXOS only has 3 flights per day, small modern turboprops, 40 psgrs, so unless you arrive by 10-10:30 you can't get their noonish flight and have a dreary airport wait. SANTORINI, on other hand, has many flights per day, on into the evening... so if you have a 1-stop or 2-stop in Europe, you still could get there by sunset. I'm guessing that, since you're not kids anymore, you might bite the bullet & go nonstop ... especially if you don't live on the East coast & thus have a flight-leg just to reach PHL-JFK-Montreal.

If you plan to fly into ATH & change for an island Start checking island flight schedules in late 2019, on Aegean & Sky Express. Aegean "newsletter" -- https://en.aegeanair.com/newsletter/?a_id=2183&related=1&session=BHtOo7mo -- alerts you to "sale" prices early in year.

As for your interests, Naxos is ideal; In late may I alway stay in St. George beach directly adjacent to Naxos Town.... easy stroll to all the attractions of town -- cafes, museums, shops, etc -- and local bus takes you to a row of other fab beaches, or to mountain villages. Great cuisine, dramatic inland landscapes, farms, ruins, history. Aaah. Go on booking.com to check it out; look at "map view" for accommodations directlyon the sand. You'll do best with 2 units, either a studio w. seaview balcony & ktichenette, or a 1-BR with main room/balcony/kitchenette. There are at least 7-8 theat are diectly on sands, or a few yards off, and if you research & reserve early, you'll get lovely units. Just a few: Studios Kalergis, Studios Thomais, Villa Naxia, Hotel Kymata, Hotel Palatia, Hotel Ippokampus, just a start. Enjoy your homework & planning - the more research, the better the experience!

I would go to Athens then pick two islands. Naxos and Paros are close to each other and make more sense than Santorini and another island, even if there are airports on each island.

You can take a ferry from/to Naxos/Paros in less than 45 minutes and you don't have to check in at an airport, go through security or wait extra for the flight.

It's really not sensible cramming 3 islands into the time you have because each time you move eats up time and time is valuable on holiday.

Since Paros and Naxos are part of the Cyclades Islands they'll be fairly similar as far as the classic white-washed houses with colorful trim. Santorini will have similar architecture.

The easiest combination will be Naxos/Paros with regular ferry runs between the two islands.

Slow down and relax and remember quality is more important than quantity.

Thank you for your helpful responses. We took the advice and booked our tickets to Athens and then reworked our itinerary. Since we don't arrive until 2:40 pm, we will fly to Santorini first, spend 2 nights, and then ferry to Naxos for 4 nights, then a 45 minute ferry ride to Paros for 2 nights, and then fly back to Athens to spend the second half of our trip in Athens and the Peloponnese. This forum post was specifically about the islands. We will definitely check out Janet's recommendations of places to stay on Naxos. We are looking at accommodations on Santorini and Paros, so would welcome any suggestions. Thank you.

Ok now that we have your arrival time I think you can easily make flights to all three islands.

Since you are interested in staying at St George beach on Naxos here are some images of the area.
St George Beach Hotels Naxos http://www.flickr.com/photos/stanbr54/sets/72157632162394787/
St George Beach Naxos http://www.flickr.com/photos/stanbr54/sets/72157632113170279/

Hoorah for you, for a workable Itinerary. As for accommodations on the other islands, just some observations:

• SANTORINI - a big challenge for enjoyment, due to the enormous tsunami of cruise crowds every weekday (a bit better if your 2 nights are on the weekend) - even so, other groups, coming on large ferries & jumbo jets, still can make for a mob scene. Strategy I've discovered is to stay in Firostephani, just on North Fringe of Fira town. Lots of rimside rooms with caldera-view balconies, an easy 10-15 minute stroll down the rim-path to the attractions of Fira...and because tour groups bypass this area, it's serene by day & night. (In fact, this past May 30, I enjoyed a nice light meal at Taverna Aktaion, seated right BY the rim wall, stayed 90 minutes, total bill about €13). AND one can take an EARLY am bus up to OIA to wander & take pix before the hordes arrive at about 10. Please avoid OIA sunset scrum! My fave Fira restaurant for sunset dinner is Stani's 3rd floor terrace.

• PAROS - Choices here depend on priorities. Port town of Parikia has most night-life, plenty of shops, restaurants, sightseeing ... lots of hotel/studio choices just at north edge of town, but the beach there however, is mediocre. There are little boats going to a nicer beach, Krios, but don't know if they run in May. Town of Naoussa at N end of Island once was a fishing village loooong ago, not for a long while, you'll see the real fishing vessels in Parikia. Naoussa is "picturesque" nice to stroll around in, feels a little "prettified" but that's just me; many adore it.. A small beach is walkable, but otherwise, you'd need a car for other beaches and to explore inland ... the bus service center is in port and bus lines extend from there like fingers of a hand, so, separate destinations.

Instead of 2 nights on Paros, you might enjoy spending those 2 nights on Antiparos, a tiny island accessible from Paros by frequent ferries. Antiparos will give you totally different experience. It's a tiny, charming, walkable place. In May, there will be hardly any tourists.

We enjoyed "A Lazy Day with Captain Ben" cruise from Antiparos ... a full day, including food and drinks and swimming, and amazing views. If you're interested, since you'd have essentially just the one day for sailing, you might contact him advance to check availability & make a reservation.

I agree with Charlene, if just 2 days, then Antiparos is perfect. I like it better now anyway... if I had a week, I'd stay in Antiparos and do the quickie little ferry 10 minutes to Paros, then a 15 minute bus, to Parikia for seeing Paros sights (the cathedral, the museum etc). Antiparos at night is MAGIC ... the winding mazey lane (Agora) is lit up, a fairyland.

Thank you so much for your responses! It really helps our planning and we follow much of the advice given. Stan, thanks for sharing your gorgeous pictures. Janet, we especially appreciate your detailed responses! We are staying at one of the places you recommended at St. George on the beach! We like that we can walk into town and use local buses to visit other beaches. We have another question. On Naxos, we would like to explore the island, visit some of the mountain villages, ruins and do some hikes. To do this, should we rent a car or rely on public transportation? If we rent a car, do you recommend one or two days?